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Amazing Grace - Old San Juan Pirate Harbor Cruise

Exceptional value.

  • Excursion Details
  • Customer Reviews

old san juan harbor tours

Points of Interest

  • Old San Juan
  • Outdoor Adventure

Description

Be sure to read the Special Notes further down this page for important requirements and restriction.

WHAT YOU VISIT Amazing Grace Topsail schooners were used during the War of Independence and the War of 1812 by both the U.S. Navy and by privateers who mastered the use of the seven sails aboard the ship, which can be used in different combinations according to the weather and wind. Your picturesque cruise departs from the Old San Juan cruise port and offers spectacular views of the historical city, accompanied by a fascinating narrated story that takes you through nearly 500 years of history. End the day with a real explosion of a historical cannon ball. Old Town San Juan, Puerto Rico (views from the schooner) Founded in 1521, Old San Juan is the second oldest city in the New World (the oldest of the U.S. and its territories). It has survived the ages under the watchful eyes of the impressive fortresses of El Morro and San Cristóbal, both built to protect this treasured city from foreign invasion. The coast offers views of the scenic waterfront promenade, Paseo de la Princesa, with its graceful fountains; the majestic governor's mansion, "La Forteleza"; and the many historic buildings that grace the skyline. WHAT YOU SEE ALONG THE WAY Spectacular coastline views if Old San Juan which occupies a mere seven square city blocks, located on the Isleta de San Juan, a small parcel of land joined to the mainland by roads and surrounded by water. Much of this charming city can be seen as you traverse the gentle Bahia de San Juan with views across the deep blue Atlantic Ocean.  Don't miss the explosion of a historical canon ball!

Special Notes:

Tour timeline may vary to avoid overcrowding, etc.

Guides will escort guests to the vessel docked by the cruise ships.

Amazing Grace

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Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

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Amazing Grace - All You Need to Know BEFORE You Go (2024)

Wasaju

Historical Walking Tours in Old San Juan, Puerto Rico

Immerse yourself in puerto rico culture, history & traditions, old san juan walking tour.

Let’s walk! Explore the historic area of Old San Juan. Step back in time, over 500 years, and learn about the island of Puerto Rico. Visit incredible landmarks while your guide regales you with cultural tales.

  • Clock 2 Hours

Why Guests Love Our Old San Juan Walking Tours

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Juan was wonderful and so informative! He is knowledgeable about the history of San Juan and PR. He is energetic, witty, and a truly enjoyable person to spend a walk with. He is a gem in San Juan!

Juan Carlos was fantastic. Even after everyone else in my group canceled, he showed up on time to give me a solo tour with a bottle of water (which I was looking for) and a sample of his very own art. His tour was a great start to my adventures in Puerto Rico. He’s a native, perfectly bilingual, and very friendly and accommodating! Highly recommend.

Juan Carlos is great and fun tour guide! I would recommend him to anyone who's looking for a relaxing and comfortable tour!

We had a great time with Juan Carlos on our walking tour. It seemed like we saw the entire island by the time we finished as we circled old San Juan and cut through streets along the way. He even brought us water bottles and some of his own artwork as a souvenir!! We learned all sorts of historical facts and memories we will take home with us.

JC it’s the best tour guide you will find in PR !!! He knows the way around PR. Highly recommend JC whenever you visit Puerto Rico.

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Private Sunset Cruise Old San Juan Harbor

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Castillo Tours DMC

San Juan Harbor Sunset Cruise

Quick Details

  • Hour Glass Duration: 2 Hours
  • Users Ages: All Ages
  • Tags Occupancy: Up to 6 People
  • Info Category: Boat Tour

Sunset Cruise in San Juan, Puerto Rico

Our charters are designed for you to relax and take in the sights of the beautiful World Heritage Site Old San Juan and its protected bay. Enjoy a scenic cruise of the San Juan Bay, the largest harbor on the island. Enjoy one of the most unique views of your entire stay in Puerto Rico as you see the sun setting behind the Islet that lies across the world-class historic site El Morro, The Governor’s Mansion, the Gate of San Juan, and the Bacardi Distillery.

Charter Includes:

  • Water, sodas
  • One bottle of house wine — the option of red, white, or sparkling

Additional Services

  • Private car service
  • Open bar (top-shelf liquor)
  • Enhanced pre-fixed menu options
  • Professional photographer
  • Combine the sunset cruise with other top activities: stand-up paddleboards (SUP), kayaks, private wave-runners/jet-ski tour, helicopter tours

Meeting Location:  San Juan Bay Marina

Related Tours

  • Most Popular
  • Info Boat Tour
  • Tags Up to 44 People
  • Users Ages 4+
  • Hour Glass 5.5 hrs

Catamaran Day Trip (Icacos Island)

Book our most popular adventure and enjoy a half-day charter full of leisure and white sand beaches as you sail on our catamaran and enjoy world-class snorkeling!

  • Info Fishing Tour
  • Tags Up to 6 People
  • Hour Glass Half-Day, Full-Day

Deep Sea Fishing Charter

Enjoy the best deep sea fishing in Blue Marlin Alley when you book our deep sea fishing charter! We offer 4, 6, and 8-hour charters.

Use promo code "onlinediscount" for 10% off when booking online!

Private Tours of Old San Juan

All Tours in Puerto Rico

Take a look at all of our private tours in puerto rico.

Whether you’re interested in Old San Juan tours, heading into a rainforest, or relaxing in Puerto Rican hot springs, Private Tours of Old San Juan has something for everyone!

Don’t see the tour you’re looking for? Create your own itinerary with our customized tour and choose your own Puerto Rico tourist attractions! No matter where we go, I look forward to showing you our beautiful island.

  • Most Popular!

The Best of Puerto Rico in One Day – Private Tour

This tour focuses on the “must-see” sights in Puerto Rico. You will get a tour of Old San Juan (know the history and culture of Puerto Rico), El Yunque Rainforest (amazing), Maria de la Cruz Caves (impressive), Loiza (culture), Pinones (beach forest) and more.

  • Up to 14 people
  • Hour Glass 7 hours
  • Tags All ages

a group of people standing next to a lake

  • Hour Glass 7 hours or 10 hours

Customized Puerto Rico Private Tour

With this customized Puerto Rico tour, I will be your personal guide for a day! We can visit caves, lagoons, rivers, mangroves, coffee plantations, historic cities, archaeological sites, small towns, research centers, rainforests, among other places.

Private Wellness Tour: Waterfalls and Hot Springs in Puerto Rico

Waterfall tours in Puerto Rico are a must-do experience! We will explore some of the prettiest waterfalls in Puerto Rico. We’ll also go to the Coamo Hot Springs which many people consider to be the Fountain of Youth that Ponce de Leon was trying to find.

El Yunque Rainforest Wellness Tour

The rain forest is a great place to relax, take pictures and learn. But is more than that. Walking in the jungle (with the right consciousness) can help you grow, connect, get inspired and become a better person.

Atlantic Coast Full Day Private Tour

During this Atlantic Coast tour we will visit some of the best “off the beaten path” destinations like Cataño for great views of Old San Juan, Isla de Cabro, the statue of Christopher Columbus (largest in the Hemisphere), caves with petroglyphs, and La Boca, a beautiful black sand beach Puerto Rico has along the north coast.

Ponce Private Tour (from San Juan)

Ponce Puerto Rico is full of archaeological sites, museums, natural wonders, architecture and hidden gems. This tour can be customized to meet your requests. Take a tour from San Juan to the historical city of Ponce!

Rainforest and Hot Springs Private Tour in Puerto Rico

Have you always wanted to go on a Puerto Rico rainforest tour? Then come along with me and we’ll see rainforests, hot springs all while learning about Puerto Rican history, culture, geography and ecological features (birds, plants, etc).

  • Hour Glass 4 hours

El Yunque Rainforest – Private Half Day Tour

Enjoy the best of El Yunque Rainforest in 4 hours.

Private Tours of Old San Juan operates under Special Use Permit from the USDA Forest Service on the El Yunque National Forest, permit number YNF22061.

San Juan Tours and Transfers

Old San Juan Historical Tour

Historical tours

Quick Details

  • User Ages: All ages
  • Hour Glass Duration: 2 hours
  • Clock Minimum Requirement: 2 tickets

Discover Old San Juan

Walk the Historical city of old San Juan on a guided tour, going back in time over 500 years. Starting at Plaza Colon and going thru the rich history of the island dating back to the natives of the island (Tainos). Walk thru the blue cobblestone streets dating back to the 1800’s and explore some of the hidden secrets from San Juan. Enjoy and explore hidden spots and legends of the most popular landmarks in the Old San Juan area, including San Felipe del Morro Fortress (1539), Capitol Building, Ballaja Barracks, San Juan Gate, San Juan Cathedral and the San Juan gate.

The whole tour offers abundant photo opportunities as we walk along cobblestone streets dating back to the 1800s, and beautiful architecture throughout the city.

If you enjoy history or just want to get better acquainted with the area you’re visiting, this Old San Juan tour is perfect for you.

Important: Tour leaves SHARP at the time of departure. Arrive at least 15 mnts early for check in and additional extra time to find parking and meeting point.

All you need is your camera and comfortable shoes.

What to Bring

  • Water bottle
  • Wear comfortable clothing

Related Tours

  • Hour Glass 3 hours
  • User Ages 18+

Bacardi Rum Distillery Tour

Have you ever wondered how rum is made? Join us to tour Bacardi’s largest distillery and sample some libations.

  • Hour Glass 4.5 hours
  • User All ages

El Yunque Rainforest Tour

Grab your sunscreen and camera and explore the rainforest with us as we visit a waterfall, observation tower, river, and more.

My Puerto Rico Tours

  • Most Popular!

OLD SAN JUAN HISTORY WALKING TOUR

Quick Details

  • Hour Glass Duration: 2 hours
  • Users Capacity: Requires a minimum of 5 participants, maximum 15
  • Walking Effort Level : This walking tour involves moderate physical activity, requiring a reasonable level of fitness or mobility. Participants must be able to complete this tour without walking aids.
  • Wheelchair Accessibility: If you have mobility concerns, feel free to contact us before booking to discuss alternative recommendations for your needs.
  • Clock Check-in: Arrive 15 minutes early for check-in before your tour.

Unveil Centuries of History in a Small Group Setting

Our walking tour immerses you in the rich history of Old San Juan. As we stroll through historic landmarks, we share the narratives woven into the streets, exploring themes of indigenous and ancestral cultural heritage, colonization, and mesmerizing architecture.

Join us on this shared adventure, peeling back the layers of Old San Juan’s rich tapestry.

  • Chevron down What's Included?
  • Guided walking tour of Old San Juan
  • Professional Tour Guide certified by the Puerto Rico Tourism Company
  • Chevron down What's not Included?
  • Entry to Castillo San Cristobal or Castillo San Felipe del Morro is not part of the tour.
  • Access to the inside of any buildings during the tour is excluded.
  • Tipping is optional but appreciated.
  • Chevron down FAQs

To ensure a smooth experience, let’s address some key details:

  • Tour Specifics This is a walking tour in its entirety.

If the minimum is not met, we will offer:

  • rebooking the same tour at a different time
  • rebooking into a Private Tour with 15% discount, based on availability
  • full-refund cancellation with 48 hours notice, giving you plenty of time to find an alternative tour.
  • Transportation Unfortunately, we do not provide transportation. Please arrange your own to our meeting point.
  • Wondering where to park your rental in Old San Juan? You can find parking options at: Doña Fela Parking, La Puntilla Parking, and Multipiso Covadonga.
  • Restrooms Restrooms are available along the walking route for your convenience.
  • Is there an additional charge associated with this tour? Online purchases include a 6% convenience fee.
  • Planning to join us on short notice? Same-day bookings are unavailable, so we recommend securing your reservation in advance for a stress-free experience.
  • Languages Spoken Our guides speak English and Spanish. Upon request, we can accommodate tours in both languages to enhance your experience.

Should you have any further inquiries, do not hesitate to reach out to us at [email protected] .

Should you have any further inquiries,  do not  hesitate to reach out to us at [email protected]

  • Chevron down Health & Safety Policy

Your well-being is our top priority!

At My Puerto Rico Tours, your safety is our paramount concern. Our Health & Safety Policy is designed to ensure a secure and enjoyable experience.

Please take note of the following detailed guidelines:

  • Hydration Essentials Remember to carry water to stay adequately hydrated during your activities.
  • Footwear Recommendations Opt for comfortable walking shoes to ensure ease and safety.
  • Weather-Appropriate Dress Code Choose light, breathable clothing suitable for tropical weather for your comfort.
  • Sun Protection Measures Shield yourself from the sun using a hat, sunglasses, and sunscreen to prioritize your well-being.
  • Weather Resilience Commitment Rain or shine, our tours go on. Stay informed on weather conditions to enhance your preparedness.
  • Chevron down Cancellation Policy

Customers will receive a full refund with 48 hours notice of cancellation. Cancellations made less than 48 hours in advance will be eligible for a 50% refund. In case of operator cancellation due to weather or other unforeseen circumstances, customers will also receive a full refund.

No-shows or cancellations on the day of the tour will not be eligible for a refund.

To cancel or inquire about rebooking your tour, please contact us:

  • Phone: +1 (939) 475-4386
  • Email: [email protected]

We appreciate your understanding and cooperation.

  • Chevron down Customer Reviews

Note: We’re Back! 🎉

After a brief hiatus, we’re thrilled to announce our comeback!

We appreciate your patience and continued support. Here’s a glimpse of what our customers have said about their experiences.

Informative, entertaining tour – highly recommended!
First time to Puerto Rico and My Puerto Rico Tours made this an awesome visit.

Thank you for being part of our journey! – Carlos & Alexandra

  • 888-366-6121 ext.3
  • [email protected]

Tour Old San Juan

  • Restaurants
  • Bars and Night Life
  • About Old San Juan
  • Child Friendly Attractions
  • Historic Places
  • La Fortaleza
  • The Legend of La Rogativa
  • A Walk Down Paseo de la Princesa
  • Old San Juan Videos
  • Old San Juan Gallery
  • Insider’s Tour
  • Night Legends & Ghosts
  • Religious Sites Tour
  • Capitol & Fort Tour
  • La Parguera
  • Gilligan’s Island
  • Caja de Muerto Island
  • A Walk Along Paseo de la Princesa
  • Vacation House and Apartment Rental
  • Grocery, Health Food Stores, and Pharmacies
  • Specialty Stores
  • Clothing, Handbags & Shoes
  • Factory Outlets
  • Art Galleries
  • Jewelry Stores
  • Events & Festivals
  • Major Holidays
  • Events in Old San Juan
  • Festivals in Old San Juan
  • San Sebastián Festival
  • Map of Old San Juan
  • Trolleys and Garitas
  • Useful Information
  • Transportation
  • Cruise Ship Travel
  • Accessibility

Disclaimer:

old san juan harbor tours

Recent Posts

  • Top Places to Eat Breakfast in Old San Juan
  • Top 10 Things to Do in Old San Juan
  • Your Risk of Covid on a United Airlines Flight is Practically Non-Existent

old san juan harbor tours

Things To Do In Old San Juan

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Ever wonder why Old San Juan is a must-visit? Picture this: a compact, walkable city brimming with history, stunning architecture, and a vibe that’s both laid-back and buzzing with life. It’s the kind of place where you can explore centuries-old forts, enjoy the local cuisine at a street-side café, and soak in the views of a sunset that lights up the harbor. Old San Juan offers a blend of experiences that caters to the curious traveler, the history buff, and the foodie in all of us.

Do You Need A Passport to go to Puerto Rico?

Do you need a passport to visit san juan.

If you’re a U.S. citizen, the answer is no—you don’t need a passport to visit San Juan, Puerto Rico. Since Puerto Rico is a U.S. territory, all you need is the same identification you’d use to fly domestically. This typically means a government-issued photo ID, like a driver’s license or ID card.

However, if you’re traveling from outside the United States, standard international travel requirements apply, and you will need a passport to enter. It’s always a good idea to check the latest travel guidelines before your trip to ensure a smooth experience.

What is Old San Juan?

It’s the historic heart of San Juan, Puerto Rico, known for its well-preserved Spanish colonial architecture, vibrant blue cobblestone streets, and a laid-back yet lively atmosphere. Imagine wandering through narrow lanes lined with brightly colored buildings, stumbling upon hidden courtyards, and soaking up views of the ocean from ancient forts.

It’s not just about the sights, though; this place buzzes with energy from its cozy cafes, lively bars, and artisan shops. Essentially, Old San Juan is a blend of history, culture, and Puerto Rican flair, all packed into a walkable area that feels like a world of its own.

Historical Gems in Old San Juan

Puerto Rico has a rich and diverse history that is deeply ingrained in its culture. The island was first inhabited by the Taíno people before being colonized by the Spanish in 1493. The colonial legacy can still be seen in the architecture of the old town of San Juan, a UNESCO World Heritage site. In Old San Juan, you can visit impressive forts like El Morro and San Cristobal, stroll through colorful streets, and admire the colonial architecture.

Puerto Rico is also home to several museums and cultural institutions that showcase the island’s history and art, such as the Museum of Art of Puerto Rico and the Museum of the Americas. If music interests you, Puerto Rico played a significant role in the development of salsa with popularizing the Afro-Spanish music traditions of Cuba. Salsa music and dancing still play a significant role in the culture today.

Old San Juan Festivals

Puerto Rico is an island that knows how to party, and they know how to do it well. Some festivals are going on every month all year long. There are even festivals and celebrations that go on all year.

These festivals are highlighted with parades, music, food, drinks, and dancing. They are a convergence of Puerto Rican culture. The best months for these festivals are December and January, and daytime is the best time to experience them. At night, they tend to get a lot more crowded and rowdier.

Great Drinks

Puerto Rico is considered to be the King of Rum, and they embrace the moniker. There are amazing innovative mixologists! All over the island, they are using Puerto Rican rum and native fruits (like passion fruits, mangoes, papayas, and more) to create a perfect taste of Puerto Rico.

Many of these mixologists also compete internationally, so they are a lot of fun to watch work. There is everything from great drinks to beautiful paired drinks and courses, and you can find it all.

I took a food and drink tour recently and it’s definitely one of the best things to do in Old San Juan. I loved that you could tie so many things into one package, a historical walking tour, a couple tasty local dishes and some refreshing drinks! You can find the link to this tour here. Here are just a few photo’s of my day.

Bacardi Rum Factory

The Bacardi Factory in Puerto Rico is the largest in the world. This factory can bottle up to 100,000 bottles a day. Aside from just touring the factory itself, you can also go on a tasting tour.

This tour allows visitors to learn all about the rum, the bottling process, and the different flavors and tastes that Bacardi manufactures. It is an important part of Puerto Rico, and it is a lot of fun. I highly suggest you take an Uber, the fumes alone make it so that you’ll need a designated driver home.

The Food of Old San Juan is …Chef’s Kiss

The “Dining Capital of the Caribbean,” is the way that many Puerto Ricans refer to their homeland. Their cuisine is a harmonious blend of Taino (the native people of Puerto Rico), American, and Spanish cuisines. These different influences combine to generate amazing dishes like mofongo (mashed plantains) and Arroz con gandules y Lechon (rice with pigeon peas and pork). This is my go to!

Things to Do Outside of Old San Juan

The island has so much to offer that it might prove impossible to try to get it all in one trip. If you happen to want to venture outside of Old San Juan, you can check out my post on different locations to visit. You’ll find it here .

Here are just a few of my top recommendations.

Head Over To Vieques

Nestled just a few miles off the southeastern coast of Puerto Rico is the island of Vieques. The tiny island of Vieques offers visitors a rich history and a plethora of exciting activities to explore. Once used as a naval bombing range by the US Navy, Vieques is now a peaceful oasis with pristine beaches, bioluminescent bays, and lush wildlife reserves.

For those with a taste for adventure, hiking, snorkeling, and kayaking are popular activities. History buffs can explore the remnants of Vieques’ historic sugar plantations. And if you’re looking for a companion getaway, don’t worry!

Vieques is just a short ferry ride away from San Juan. If you are more adventurous, you can take a small plane. I don’t have the stomach for it!

But, if you’re looking for an island paradise that’s both rich in history and filled with excitement, head down to Vieques and experience all that this enchanting island has to offer!

Vieques is the home of a beautiful bioluminescent bay, and El Yunque is the location of the only subtropical rainforest in the United States. Below are my top three tours of El Yunque rainforest.

Don’t Forget Water Fun

No matter where you are going in the Caribbean, the beaches and ocean are an essential part of the trip. In Puerto Rico, areas like Culebra, Vieques, and El Yunque are great places to visit. Culebra is the perfect spot for snorkeling and scuba diving. Flamingo Beach in Culebra offers the ideal backdrop for your snorkeling and diving adventure. Below are a few of my top suggestions.

Which Things to Do in Old San Juan Will You Do?

Whether you’re a history enthusiast, a food lover, or a seeker of authentic experiences, Old San Juan offers something special for everyone. If you’re ready to turn this virtual adventure into a reality, our team of travel experts is here to craft a personalized itinerary that brings your dream vacation to life. Contact us today!

The post Things To Do In Old San Juan appeared first on Teach Travel Discover .

Ever wonder why Old San Juan is a must-visit? Picture this: a compact, walkable city brimming with history, stunning architecture, and a vibe that’s both laid-back and buzzing with life. It’s the kind of place where you can explore centuries-old forts, enjoy the local cuisine at a street-side café, and soak in the views of...

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In Washington State's San Juan Islands, Time Stands Still and Nature Reigns Supreme

By Jesse Ashlock

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All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

On a still summer morning on Washington State 's Orcas Island , I rented a pair of tandem kayaks from a sleepy-eyed, flaxen-haired attendant barely out of her teens, who quickly returned to painting watercolors in the tall grass beside the weather-beaten sales kiosk. A gentle wind went shhh through tall hemlocks as my family paddled, two by two, to a rocky islet at the center of Mountain Lake, on the flank of Mount Constitution. There we clambered ashore, and the kids, Agnes and Rex, immediately began darting among the lodgepole pines, collecting sticks and pine cones to build fairy houses. Aside from the faint smell of a forest fire burning in the Cascades and a smudge of smoke on the eastern sky, it could have been a scene from my own childhood.

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Aboard the ferry from Anacortes to Friday Harbor

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The Sugar Shack, an ice cream shop beside Cascade Lake on Orcas Island

When I was eight years old, my mother moved my three younger brothers and me to Anacortes, a small island town about two hours north of Seattle . It is the gateway to the San Juan Islands, an archipelago within the Puget Sound and the broader Salish Sea, which divides Washington State from Canada . As an underemployed single mom to four young boys, she needed inexpensive outlets for our considerable energy. Taking our bikes onto the ferry and spending the day in the San Juans was an ideal solution. Certain activities here—huddling inside beach forts assembled out of bleached driftwood, waving at cars while cycling along the agricultural back roads of Lopez Island, watching from the second deck for the underwater “burp” of the ferry as it departs a port—are woven into the helices of my DNA. But I hadn't been in more than two decades. So I booked a trip, to show the islands to my kids, to reconnect with them as an adult, and perhaps to have a few experiences that were out of reach for me as a child. As an added bonus, my mom came along too.

We posted up in a cozy log cabin at Lakedale lodge, a rustic mini kingdom on the island of San Juan, about 10 minutes from the main town of Friday Harbor. To enter, you cross a small causeway—the compound is an island within the island. Karl Bruno, Lakedale's well-seasoned general manager, told me that its founders were pond builders, who in the late ’60s convinced the county to raise the road so that they could create the three lakes around which the resort is now arranged. For a generation it was a campground only, but today there are yurts and canvas cottages in addition to the cabins and tranquil main lodge. Families come back every summer to play life-size checkers and chess, construct birdhouses, and fish in the lakes for cutthroat trout. Sometimes the kids return as grown-ups to have weddings here.

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Morning on the sound with Western Prince Whale Watching Adventures

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A guest at Lakedale lodge ready to go fishing

Friday Harbor, a charming village that spills up a steep hill from the ferry terminal, looked just as it had 35 years ago, though I suspect that when I was little, the cafés were less chic and the sandwich shops not quite so artisanal. Certainly, the San Juans today have more private islands owned by tech billionaires and more boho big-city refugees, many of whom arrived during the pandemic, than they once did, but this is a place whose residents like things to stay as they are. At Vic's Drive-In , a classic diner on the outskirts of Friday Harbor that claims to be the island's longest continuously operating restaurant, co-owner Brian Carlson, a predecessor of Karl Bruno at Lakedale, tells me about the outrage when a previous owner tried to change the name to Vic's Driftwood Drive-in. Why? “Because it's Vic's, and people in Friday Harbor hate change.” Driving through the woods of Orcas, I kept noticing signage that felt as if it could have been there 50 years ago: “American Legion Sunday Morning Pancake Breakfast”; “Orcas Island Jazz Festival”; “Indralaya, a Theosophical Society.” And, nailed to a telephone pole by a driftwood-strewn beach near the charming town of Eastsound: “Be Kind.”

But what most teleported me back to childhood was the San Juans' eternal landscape, especially its shorelines. On the other side of San Juan Island at Lime Kiln Point , one of the area's best places to spot whales , the kids and I clambered around the igneous rock formations splayed beneath the quaint 106-year-old Lime Kiln Lighthouse, marveling at the tenacity of the madrones that clung to them. Across the Strait of Juan de Fuca we could see the Olympic Peninsula, indistinct in the haze of the wildfires. If the day had been clear, I knew from memory, we would have been able to see Mount Rainier seeming to float on the southern horizon. On the Shark Reef Sanctuary Trail on sleepy Lopez, we emerged from old-growth fir trees to traipse along the bluffs, looking for crabs in tide pools, marveling at the countless barnacles, and observing a colony of sea lions sunning themselves on a rocky outcropping a few hundred feet offshore.

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A canvas cottage at Lakedale on San Juan Island

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Alpacas at Krystal Acres Alpaca Farm on San Juan Island

Later that day we went to Spencer Spit , where a sandy beach separates a quiet saltwater lagoon from the sound. Well-fed clouds, almost too substantial to be believed, floated above islands carpeted with evergreens, cheerful sailboats, and a poky ferry slowly gliding along the navy blue waters. My kids found a driftwood fort taller than me, with a plank you could move aside affixed with a sheet of paper that was labeled “Door.” They quickly joined forces with siblings from Oregon and embarked on an ambitious series of home improvements: patching up holes, putting in furniture, erecting a seaweed flag. There was already a lump rising in my throat when my mother turned to me and asked, “Does this remind you a lot of childhood afternoons?”

Something I never got to do as a kid was eat at nice restaurants, and there are so many on these islands that make ingenious use of the region's beautiful ingredients. Perhaps our favorite meal was at Buck Bay Shellfish Farm on Orcas, where we ate oysters on the half shell and seafood rolls artfully adorned with edible flowers at a picnic table steps from the bay where the restaurant grows its own crustaceans. Chi, my wife, trapped the persistent yellow jackets under spent oyster shells until a waiter arrived with lavender oil and instructed us to apply it to our wrists to ward off the insects.

I definitely never got to go on a whale-watching tour, so I booked one with Western Prince Whale Watching Adventures . Ivan Reiff, its owner and captain, bought the business more than two decades ago, motivated by a desire to escape the rat race and make a living on the water. Our guide was Katie Jones, a veteran naturalist who also works at the Center for Whale Research in Friday Harbor. “I'm going to stick my neck out and say orcas are some of the most social animals on the planet,” she said. “More social even than we are.” Before long, we found a pair: Sprinter, a 20-year-old adult male, and Esperanza, born in the 1960s and presumed to be Sprinter's grandmother. We followed them for 45 minutes as they cruised along, hunting harbor seals near a rocky outcropping covered with cormorants and other nesting birds. The sharp black triangles of their dorsal fins felt like the yin to the yang of the white sails dotting the sound.

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The porch of the Outlook Inn in the village of Eastsound, on Orcas Island

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Inside a log cabin at Lakedale

We ventured briefly into Canadian waters, then passed Turn Point Light Station , atop the striated sandstone walls of Stuart Island. The depth of the sound here reaches 1,300 feet. These islands, Katie observed, are just the tops of the mountains; their southern sides are often barren because of the movement of the glaciers which carved out the Salish Sea 10,000 years ago. In the place where our boat was, there once would have been a mile of ice above our heads. I realized right then that even if I'd had no childhood connection to the San Juans, I still would have found visiting them as an adult to be astonishing.

The feeling of wonder continued that evening, when Chi and I left the kids with my mom and ventured out onto the water at dusk with Discovery Sea Kayaks to experience the bioluminescent wonders of the noctiluca. This millimeter-long single-celled organism thrives in the deep, cold, nutrient-rich waters of the Salish Sea, especially during the long days of summer, which give it time to recharge. It operates according to circadian rhythms, growing brighter as the night goes on. Our guide was Kelly Yelverton, a Colorado native who'd been in the San Juans since 2010. She was assisted by Caleb Johnson, a native of Beaumont, Texas , who'd been traveling with his wife in a van for the past five years, doing seasonal work and hiking. They'd just been in Colorado for the wildflower season and planned to go next to North Dakota to work a beet harvest. “We just work different gigs and try to spend as much time outside as we can,” he told me.

As the sky darkened, the water began to glitter. There are many things you can do with a paddle to create different patterns, but my favorite was plunging it in vertically and watching plumes of dense sparkles emanate from the shaft. I felt like Poseidon. We paddled to dark waters near the privately owned Dinner Island, where two gorgeous modernist homes sat. There the water was so full of light it was as if we'd entered another world. We saw flashes as fish passed beneath our kayaks, then a bright column that rose to the surface. It was a harbor seal cavorting around us. Rain fell for a few minutes; each drop transformed into light as it hit the water.

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A view of the inlet from the village of Eastsound

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Buck Bay Shellfish Company, on Orcas Island

The scent of rain lingered as we paddled back. Kelly told us about being out with guests during the Perseid meteor shower, the drama downstairs matched by the fireworks above. “There were a lot of sore necks,” she recalled. Before we wrapped up, she took us to a secluded cove and pointed out the house where Stan Lee, the Marvel Comics legend, had once lived. “I like to think,” she said, “that walking this land gave him the inspiration for some of the superheroes he created.”

Besides the summer wildfires and ubiquitous burn bans, the biggest change I observed in the San Juans was to the ferry system. Actually, the ferries themselves—battered, hulking brutes, some dating to the Johnson administration, that glide ploddingly along the Puget Sound, their white masses contrasting with the blues and greens of the landscape—have scarcely changed at all. But the system, the largest in America, has grown increasingly decrepit and unreliable. “I've exhausted myself reaching out to our senators and congresspeople, telling them, ‘We have a problem here,’ ” Karl Bruno told me. “But it's hard to get noticed.”

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The system had been strained for years due to defunding of the Washington Department of Transportation and mandatory ship retirements, but worker attrition during the pandemic made things worse. And yet one could argue that there is a silver lining in all of this. The islands' inaccessibility has always been central to their charm, and a reason for their relative imperviousness to change. If you made the fleet bigger and faster, would the San Juans still be the San Juans? This is a place that is made for slowing down, getting away from it all, savoring the simple pleasures, having nowhere to be anytime soon. And we need these kinds of places more than ever these days.

After our last ferry ride, my family spent a few hours on Fidalgo Island, where my childhood hometown of Anacortes is located. We walked across Deception Pass Bridge , the magnificent set of cantilevered spans that soars over the strait separating Fidalgo from Whidbey Island , before heading down to Bowman Bay, where my mom said I'd kayaked for the first time, to stroll along one more rocky beach before driving to Seattle . My children swung pieces of bullwhip kelp that had washed ashore and discovered another driftwood assemblage, for which they began constructing an addition. You can find the best, perfectly round, flat skipping stones on these beaches, so we collected a bunch and I schooled them on technique. The sun was setting as I maneuvered the car out of the parking lot, feeling grateful that this northwestern corner of Washington is still a place that fresh generations of children come to, instantly make new best friends, and set about the important work of building forts and fairy houses.

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A driftwood fort on South Beach, on San Juan Island, looking out at the Strait of Juan de Fuca

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Goods for sale at the Market Chef

Where to stay

San Juan Island

Lakedale , 10 minutes from Friday Harbor, has grown up from its ’60s roots as a hippie campground. Families love the log cabins, canvas cottages, and yurts with Scandi-style interiors; the tranquil main lodge is adults-only. From playing life-size chess and tie-dyeing T-shirts in the activity tent to pop-up concerts at the edge of the lake, there is no shortage of fun things to do on-site.

Orcas Island

The Outlook Inn with 40 bright guest rooms has lived many lives since it was a general store in the 1890s, but one thing that has never changed is its great location. A prime address on Main Street in Eastsound puts it about 15 minutes from both the ferry landing and Moran State Park and a short walk from the town's finest shops and restaurants, with amazing views of Fishing Bay.

Multiple islands

For large groups, travelers seeking extra space (bikes and kayaks take up lots of room), or gourmands wanting to prepare their own alfresco feasts using the area's amazing summer bounty, a rental house is a great way to go. Northwest Island Escapes , a locally owned and staffed management company, has the San Juans' largest selection, with marvelous properties on Orcas, San Juan, and Lopez.

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The house salad at Coho, a restaurant in Friday Harbor

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A server at the Market Chef, an artisanal sandwich shop and provisions store in Friday Harbor

Where to eat

Start your day at Bakery San Juan with a cheese claw, a cinnamon roll, or a pain au levain batard that will bring a tear to your eye. It's one of the finest bakeries you will ever patronize. No joke. Since 2019, chef Ryan Lockhart has helmed the kitchen of historic Craftsman Coho Restaurant near the Friday Harbor ferry landing, serving highly regarded dishes that elevate the local ingredients. Forest hideaway Duck Soup calls itself a country restaurant, which is borne out by the rustic environs. But its artfully plated dishes, which interpret the Pacific Northwest through a global lens, will appeal to gourmands.

Beat the crowds that gather early on the porch of Eastsound favorite Brown Bear Baking and score a flaky kouign-amann and a morning bun. One of the most pleasant eateries in all the islands, Buck Bay Shellfish Farm offers a seafood-heavy menu (halibut ceviche, salmon sliders), tasty Washington wines, and a lovely alfresco setting. Located on the edge of Eastsound, Houlme serves inventive pizzas, Mediterranean-tinged small plates, and natural wines in its dining room or backyard.

Surrounded by heirloom plum orchards, the restaurant with water views at 1869 farmhouse Inn at Ship Bay sources as much as it can from Orcas—including the lamb it serves with quince grown on-site. While not fussy, it's about as fancy as the island gets. After a hike in Moran State Park, stop at Sugar Shack for tasty waffle cones from Lopez Island Creamery—the fruit flavors, like wild blackberry, are especially memorable.

Where to play

One of most seasoned operators in the region, Discovery Sea Kayaks offers sunset and bioluminescent tours, half- and full-day paddles, and overnight experiences. If you're traveling with kids, stop by The Farm at Krystal Acres , a 40-acre family-run on the west side of the island to feed the fleecy critters, then hit the shop to purchase alpaca socks, beanies, yarn, and more. Lime Kiln Point State Park , on the western edge of San Juan, is one of the best places on Earth to watch whales from land and an example of the numerous great state parks in this part of Washington.

In addition to orcas, you may see migrating baleen whales, not to mention seals and sea lions, bald eagles, and more, in the company of warm and knowledgeable guides at Western Prince Whale Watching Adventures . What's especially wonderful about The Whale Museum in Friday Harbor is the layered cultural history it tells about these remarkable mammals, as well as the intense pressures human activity has placed on them. Amazing for kids.

Orcas's best hiking and swimming can be found within 5,250-acre Moran State Park . There's an easy 2.7 mile hike around Cascade Lake and pedal boats and SUPs to rent. A bit higher up, Mountain Lake has more challenging trails and kayaks. For panoramic views, head to the lookout tower at the summit of Mount Constitution. Master potter Jerry Weatherman has turned out stunning ceramics with island-inspired shapes and glazes at his studio and showroom, Olga Pottery , since 1979.

This article appeared in the May/June 2024 issue of Condé Nast Traveler. Subscribe to the magazine here .

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‘Pirates of Penzance’ brings local touches to an old classic

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Contributed photo by Kelley Balcomb-Bartok Fredric (Cody Balcomb-Bartok), the Pirate King (Patriqi Holahan) and Ruth (Jill Urbach).

old san juan harbor tours

Contributed photo by Kelley Balcomb-Bartok Fredric (Cody Balcomb-Bartok) listens to the Pirate King (Patriqi Holahan).

old san juan harbor tours

Contributed photo by Kelley Balcomb-Bartok The Pirate King (Patriqi Holahan) with the General (Mason Turnage) in the background.

old san juan harbor tours

Contributed photo by Kelley Balcomb-Bartok The Pirate King (Patriqi Holahan) and his band of pirates.

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  4. Old San Juan Sunset Sail

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  1. Old San Juan Sunset Sail on 19th-Century Style Schooner 2024

    Overview. Float past hundreds of years of history and picturesque scenery during this 2-hour sunset sailing excursion in Old San Juan Harbor. Climb aboard the "Amazing Grace," a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area.

  2. Amazing Grace Harbor Tour of Old San Juan

    Amazing Grace Harbor Tour of Old San Juan. Old San Juan now has a great new tour option, the Amazing Grace! Now you can take a tour of San Juan in a top sail schooner, the same type used to fight the British in the American war for independence and the War of 1812. East Island Excursions runs 4 tours a day - 3 day tours and one sunset cruise.

  3. 2024 Old San Juan Harbor Sailing Tour

    Old San Juan Harbor Sailing Tour. See San Juan from a new perspective on this easy 1.5-hour boat cruise through the harbor. The deck of the traditional 19th-century-style schooner offers frame-worthy views of the coast and historic landmarks like La Fortaleza and Paseo La Princesa. Enjoy snacks and drinks on board and be sure to keep your eye ...

  4. Excursions

    Your picturesque cruise departs from the Old San Juan cruise port and offers spectacular views of the historical city, accompanied by a fascinating narrated story that takes you through nearly 500 years of history. End the day with a real explosion of a historical cannon ball. Old Town San Juan, Puerto Rico (views from the schooner) Founded in ...

  5. Amazing Grace

    Amazing Grace. NEW Old San Juan harbor sail! Come join us The adventure begins from Old San Juan cruise between pier 3& 4, where you can take in the enchanting views of this cultural city. Enjoy the beautiful sites around the bay, the Spanish fort "El Morro", La Fortaleza "Governor's mansion", Paseo La Princesa and more.

  6. Old San Juan Cruises & boat tours

    1. Old San Juan: Sunset Cruise with Drinks and Hotel Pickup. Gaze at a beautiful sunset on this cruise through Old San Juan from San Juan or Carolina. Sip delicious cool drinks and a variety of appetizers while relaxing aboard the boat, and absortbing the views from the harbor as the Old City's day turns to night.

  7. Old San Juan Harbor Sailing Tour

    Set sail on a 19th-century style schooner for a journey through time, taking in more than 500 years of history. Uncover the beauty of Old San Juan, El Morro, La Fortaleza, and Paseo La Princesa from the water on this 1.5-hour tour, admiring important landmarks and stunning landscapes as you go. Keep an eye out for dolphins and beverages are include

  8. Wasaju Walk San Juan

    Old San Juan Walking Tour. From $35. Let's walk! Explore the historic area of Old San Juan. Step back in time, over 500 years, and learn about the island of Puerto Rico. Visit incredible landmarks while your guide regales you with cultural tales. Book Now.

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    A Day in Paradise. San Juan Mini Boats. Icacos Snorkeling Beach Tour. Culebra Snorkeling Beach Tour. Vieques Full Day Beach Tour. Charters. Luxury Private Catamaran. Private Power Catamaran. Culebra Island Charters.

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    Description. 48 ft Power Boat charter. Our charters are designed for our guests to relax and take in the sights of beautiful World Heritage Site Old San Juan and its protected bay. Enjoy a scenic cruise of the San Juan Bay, the largest harbor on the island. During the months of December to February, the tour time will be 4:30pm-6:30pm, as the ...

  11. Amazing Grace

    Amazing Grace, San Juan, Puerto Rico. 32,394 likes · 1 talking about this · 1,553 were here. Departing from Old San Juan cruise port, you will take in the beautiful views of our Old San Juan...

  12. San Juan Sunset Cruise

    Combine the sunset cruise with other top activities: stand-up paddleboards (SUP), kayaks, private wave-runners/jet-ski tour, helicopter tours. Meeting Location: San Juan Bay Marina. Tweet. Join the captain and crew at Castillo Tours in Puerto Rico for a relaxing and informative boat tour of Old San Juan Harbor. Book your private charter now!

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    The Best of Puerto Rico in One Day - Private Tour. From $398.00. This tour focuses on the "must-see" sights in Puerto Rico. You will get a tour of Old San Juan (know the history and culture of Puerto Rico), El Yunque Rainforest (amazing), Maria de la Cruz Caves (impressive), Loiza (culture), Pinones (beach forest) and more. Book Now.

  14. Forts

    Forts El Morro and San Cristóbal along with 2.5 miles of city wall complete a fortification system that protected Puerto Rico, San Juan harbor and much of Spain's interests in the "New World" from pirates and foreign invasion. Spain spent over 250 years building and fortifying this system considered "state of the art" for its time ...

  15. Old San Juan Historical Tour

    Discover Old San Juan. Walk the Historical city of old San Juan on a guided tour, going back in time over 500 years. Starting at Plaza Colon and going thru the rich history of the island dating back to the natives of the island (Tainos). Walk thru the blue cobblestone streets dating back to the 1800's and explore some of the hidden secrets ...

  16. Old San Juan Harbor Sailing Tour

    Float past more than 500 years of history and picturesque scenery during this 1.5-hour sailing excursion in Old San Juan Harbor. Climb aboard the 'Amazing Grace,' a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you'll enjoy up-close views of Old San Juan sights such as El ...

  17. Old San Juan Tour

    Duration: 2 hours. Users. Capacity: Requires a minimum of 5 participants, maximum 15. Location. Location: Meet us at Plaza Colón in Old San Juan. Walking. Effort Level : This walking tour involves moderate physical activity, requiring a reasonable level of fitness or mobility. Participants must be able to complete this tour without walking aids.

  18. Old Harbor

    About Old San Juan; Forts; Child Friendly Attractions; Historic Places; La Fortaleza; Plazas and Parks. The Legend of La Rogativa; A Walk Down Paseo de la Princesa; Museums; Blog. Blog; Old San Juan Videos; Old San Juan Gallery; Walking Tours. Insider's Tour; Night Legends & Ghosts; Religious Sites Tour; Capitol & Fort Tour; Other ...

  19. Old San Juan Harbor Sailing Tour

    Float past more than 500 years of history and picturesque scenery during this 1.5-hour sailing excursion in Old San Juan Harbor. Climb aboard the 'Amazing Grace,' a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you'll enjoy up-close views of Old San Juan sights such as El ...

  20. Things To Do In Old San Juan

    It's the kind of place where you can explore centuries-old forts, enjoy the local cuisine at a street-side café, and soak in the views of a sunset that lights up the harbor. Old San Juan offers ...

  21. In Washington State's San Juan Islands, Time Stands Still and Nature

    San Juan Island. Lakedale, 10 minutes from Friday Harbor, has grown up from its '60s roots as a hippie campground. Families love the log cabins, canvas cottages, and yurts with Scandi-style ...

  22. Old San Juan Sunset Harbor Tour 2024

    Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck. Then, spy highlights like Paseo De La Princesa, La Fortaleza, the San Juan City Walls, and more, all while the sun goes down. Light refreshments and alcoholic drinks are ...

  23. 'Pirates of Penzance' brings local touches to an old classic

    For those who love a good laugh and pirates, "Pirates of Penzance" will be performed at the San Juan Community Theatre opening May 10 and running through the 26. "I cannot wait for the audience to see the pirate ship roll onstage, or for them to see many of the local touches from around the island. This is a production of Pirates of ...