backroads tuscany trip

Review Of Backroads Tuscany Biking Tour

Thinking of taking a bike trip in Tuscany? I just went on the Backroads Chianti region biking tour in Tuscany and I’m here to give you a review and the full scoop on what to expect.

Backroads is a leader in guided bike tours in the United States and around the world. The company aims to provide the perfect vacation that combines activity and luxury.

This was my first bike tour in Europe, my first ever bike tour actually. Tuscany is an amazing place both to visit and to bike through. The scenery is stunning; it’s like biking through paradise.

But biking is not Tuscany’s only draw. With a wonderful combination of culture, food, and wine, Tuscany is synonymous with  la dolce vita . And Backroads does everything to pamper you and make you feel this vibe.

The region conjures images of vine-covered rolling hills, olive groves, and honey-toned hilltop towns. You may feel like you’re biking through a fresco.

The Backroads Tuscany biking tour lasted 6 days and 5 nights. We began in Arezzo and ended in Florence.

How To Get To Arezzo

Because the Tuscany bike tour starts in Arezzo, you’ll want to fly into Rome’s Fiumicino Airport. That’s the closest airport.

Plan to arrive at least one day in advance, maybe 2, in case there’s an airline snafu. You don’t want to miss the first day of your tour.

You can spend one day in Rome or head directly to Arezzo. Underrated Arezzo is definitely worth visiting.

After you collect your bags, head to the Felice Santini train station just outside the airport and take the Leonardo Express to Rome’s central Termini Station.

You should book a Leonardo Express ticket in advance . Trains depart every 15 minutes.

The Leonardo Express drops you off in Rome’s Termini Station, which is in northeast Rome. From there, you can take the train to Arezzo.

If you don’t want to take the Leonardo Express, you can book a private transfer from the airport to Termini Station.

The cabs at Fiumicino are notorious for ripping off tourists, so this is a good alternative. Your driver will be waiting outside baggage claim holding a sign with your name on it.

From Rome Termini Station, 40+ trains leave daily for Arezzo. The journey takes about 2 hours.

You should also book a ticket in advance for the Rome-Arezzo leg of the journey on Trenitalia . Be sure to validate your ticket before getting on the train.

Arezzo’s train station is just a 10 minute walk from its historic center. We were able to navigate with our bags fairly easily.

If this sounds all too complicated, you can also have your travel agent arrange a private transfer directly to Arezzo

This isn’t a bad option when you’re jet lagged. But it’s very expensive (possibly $500+).

Review of Backroads Tuscany Biking Tour

Here’s my honest review of everything you can expect on a bike tour with Backroads in Tuscany, with detailed information on the bikes, the biking routes, the hotels, and must know tips.

1. What To Expect On A Backroads Biking Tour

First off, you can expect to have outstanding guides. Our principal guides were Simone and Massimo, with a couple other guides providing support.

They were knowledgeable, extremely professional, provided personal service, and flawless execution. You won’t have to spend a second worrying about the logistics of your tour.

The guides are also exceedingly friendly. Their top concern is that you have the best experience possible and will move mountains to make sure you do.

Bike Options

There are four kinds of bikes you can ride on this particular tour– titanium performance bike, upright touring bike, or electric bike. For $500, you can upgrade to top-of-the-line lightweight carbon bike.

You’ll need to choose your bike in advance, so it’s worth putting some thought into your selection.

I don’t personally recommend using the touring bike. It’s very heavy and Tuscany is very hilly. You need something lighter.

In fact, you need to be in darn good biking shape to use the performance bike in Tuscany. I had thought Tuscany was gently rolling hills. Turns out, there’s some wicked long climbs and some of the climbs are rated for pro bikers.

For many, especially if you’re an inexperienced biker, an e-bike may be the best option.

I had booked an upright touring bike initially. But I began the biking tour with a sinus infection.

At my request, the guides found an e-bike for me. This was perfect because, even I had been completely healthy, I think the hills would have been too much for me.

Using An Electric Bike

With an e-bike, you can let the bike do all the work. Or, you can still get a something of a workout in.

The e-bikes have 3 speeds — easy, medium, and turbo. If you put the bike in turbo, that’s the easiest speed for the rider.

But the e-bikes don’t go over 20 kilometers an hour. If you go faster, you’re doing all the pedaling and all the work.

The best thing about the e-bike? Climbing tough hills is a breeze.

My husband couldn’t keep up with me on the hills when I used the turbo setting. But that meant I could stop and take some photos while he caught up.

2. Who Goes on A Backroads Tour?

There will be 16-26 people on your tour. On ours, in mid-May, there were 18. Quite a few of these people will likely be repeat customers.

This tour was for couples, solos, and friends. There were no children.

The age of people on Backroads tours skews to middle age. But on my “adults only” tour there was a range of ages from adult children traveling with their parents to those in the 60+ age group.

There were some excellent bike riders. And there were some non-athletes who were completely happy on their e-bikes. So a Backroads tour is really suitable for all skill levels.

3. What I Didn’t Expect On A Backroads Tour

Looking at the itinerary, you might conclude, as I did, that there were 3 groups of riders. That isn’t the case.

There are typically 3 distances — a morning ride, a post-lunch ride, and an extra ride for those who want to do more.

You usually start the day around 9:00 am and, if you select the longest ride, you return at 3:30 pm to 4:00 pm. (You’ll have some time to lounge at the pool or relax before dinner.)

People don’t ride in groups. People tend to ride as couples. And, with different skill levels, the riders are spread out over the bike route.

You’ll be given a GPS. This surprised me. I hadn’t realized I’d be navigating myself.

The GPS is quite small. If you need reading glasses, you might have trouble reading it. You can zoom it, but that makes it hard to know when a turn is coming up.

My husband and I are at very different bike skill levels. He’s an expert rider and I just work out casually on the peloton bike. I had thought I’d have a slower group to ride with, but that’s not the case.

If you and your spouse are at different levels, one of you might need to use an e-bike if you want to ride together.

I don’t really advise biking solo, unless you’re a very experienced rider. I felt like I could have gotten lost.

But there will be a Backroads rider on the course making sure that people make it through the checkpoints and don’t get lost. Another one or two will provide van support.

If you do get lost, help from Backroads is just a text or phone call away. You’re given the phone numbers of the guides just in case.

At various stops along the way, Backroads provide drinks and snacks for those who need it. This is where you can refill your water bottle and add some electrolytes.

They also shuttle people back to the hotel if they’ve had enough riding for the day.

I also didn’t expect it to be so hot in mid-May. It was over 85 by midday most days, though it would cool off at night. You’ll need to drink water frequently to avoid dehydration.

4. Review of Backroads Tuscany Itinerary

The best thing about Backroads is the extraordinary care they take in designing the tour itinerary.

It’s the perfect mix of breathtaking landscapes to pedal through, great food and wine at various agriturismos and restaurants, and a hefty dose of culture.

Here’s a quick recap of what we did on our Tuscany Backroads tour:

Arrival in Arezzo:

We took a private transfer to Arezzo from Rome. We did this because, as a travel blogger, I wanted to have a solid day to see Arezzo’s top attractions .

If you arrive in time to do some sightseeing, you should try to see:

• Piazza Grande, Arezzo’s gorgeous central square
• the famous Piero della Francesca fresco cycle in the Basilica of San Francesco
• Casa Vasari , a charming house museum with frescos by Giorgio Vasari
• Arezzo Cathedral
• Church of La Pieve

We had a delicious lunch at Antico Forte.

Take a bus from Arezzo to a farm to table lunch spot. Get a debriefing on what to expect on your Tuscany bike tour.

Bike in the afternoon. Check into your hotel, the Borgo San Felice. Group dinner.

Morning bike ride through the Chianti region. Fabulous lunch at Badia a Coltibuono , a former 11th century abbey.

Afternoon ride. Wine tasting and a “ grigliatia ” (mixed grill) group dinner under grape vines at the hotel.

Morning ride of 25 miles. Lunch at Il Pereto , an organic farm. In the afternoon, ride the famous Crete Senesi loop.

Shuttle to Siena for a contrada tour where you learn all about Siena’s famous medieval horse race, The Palio . Dinner on your own in Siena, with plenty of restaurant recommendations.

Morning ride to the ancient hilltop town of Raada in Chianti, with a stop at a ceramics store. After lunch, ride the rest of the way to your next hotel, Castello del Nero. Dinner at the Michelin restaurant, La Torre .

Morning ride to San Gimignano . Lunch and free time in the famous medieval town up to 2.5 hours. Afternoon ride on the San Donato loop back to Castello del Nero. Cocktail hour and final group dinner.

Optional morning bike ride. Shuttle bus to Florence Airport, where you’ll arrive around noon. From there, you can get a taxi into Florence or proceed to your next destination.

Deviations From The Itinerary

You don’t have to do everything on the itinerary. You can take the afternoon off. For example, on day 2, I went to Siena in the afternoon to explore instead of riding more.

5. The Premiere Hotels

No review of Backroads would be complete without discussing your accommodations. We stayed in two hotels. Both were gorgeous.

Borgo San Felice is about a half hour from Siena. Castello del Nero is about a half hour from San Gimignano. Both are five star hotels.

Borgo San Felice has a cozy (but luxe) step back in time feel. The charming hotel consists of a series of perfectly restored stone mansions, which were once a medieval hamlet.

It’s at the top of a hill surrounded by vineyards and olive orchards.

The grounds are immaculate, with flowers blooming everywhere. There’s a lovely pool and the rooms are spacious.

We had a suite with a separate sitting area and a huge bathroom with a hot tub.

The buffet breakfasts every morning were memorable, with farm to table honey, cheeses, and produce.

Castello del Nero is a renovated 12th century castle and has a real “wow” factor. It’s grander than Borgo San Felice. The views from the restaurant’s panoramic terrace were stunning.

The rooms are elegantly modern with muted colors and stone floors. You’ll have 20 foot ceilings and splendid views of the countryside through long windows.

There’s a Michelin restaurant onsite. And a large pool (you can do laps) and lounging area. The castle is perched up high, so you have dramatic views over the countryside.

6. Final Thoughts

Overall, the Backroads experience was exceptional. With the unsurpassed service and luxury, you may feel like it’s the trip of a lifetime.

Hopefully, I’ve provided you with a good overview of what to expect on a Backroads biking tour, so you don’t have any surprises.

I’m already planning my next Backroads biking tour!

I hope you’ve enjoyed my review of Backroads Tuscany biking tour. You may enjoy these other Tuscany travel guides and resources:

• 1 day itinerary for Florence
• 3 day itinerary for Florence
• Best museums in Florence
• Hidden gems in Florence
• Best things to do in Montepulciano
• 1 day itinerary for Siena
• 1 week in Tuscany itinerary
• 10 day itinerary for Tuscany
• Tuscany art bucket list
• Top Attractions in Pisa

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Last Updated on July 2, 2022 by Leslie Livingston

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Places You’ll See

• Introduction
• Day 1 Florence (Italy)
• Day 2 Florence – Lucca
• Day 3 Lucca – Cinque Terre – Lucca
• Day 4 Lucca – Pisa – Volterra
• Day 5 Volterra – San Gimignano and Siena – Pienza
• Day 6 Pienza
• Day 7 Pienza – Rural Tuscany
• Day 8 Rural Tuscany – Florence

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Here at Back-Roads, our passion is delivering small group holidays that delve a little deeper. Travelling by luxury mini-coach along scenic roads, our tours invite you to see each destination through the eyes of the people who know it best: the locals who call it home. We know that the best kind of adventure is one that introduces you to authentic experiences, never-to-be-forgotten views and hand-picked retreats brimming with local charm – while providing you with the time and space to explore independently. With intimate group sizes and expert Tour Leaders and Drivers, there’s no better way to feed your curiosity than with a Back-Roads tour.

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Customer Reviews

• Overall Rating Good 4.0
• Itinerary Good 4.0
• Guide Average 3.0
• Transport Good 4.0
• Accommodation Average 3.0
• Food Average 3.0
• Tour Operator Back-Roads Touring 4.4
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• EV Elaine · 2nd July 2023 Very good tour. Good value for the money. Loved all the sights and off the beaten path adventures. Trip date: June 2023

• C CherylMarley · 15th October 2019 The tour was exactly what we wanted. It took us to the places we wanted to see, provided the experiences we were after, in a small group with friendly and expert assistance. However with Flavio as our guide, we were provided with even more than we... Show more Trip date: May 2019

• J JohnPalmer · 14th October 2019 Flavio and our driver Pablo really made the tour. He was very inclusive and took care to ensure slower people were looked after. Always cheerful, ready with a joke or story and filled us in on 'local' practices and italian 'sign' language!! A real... Show more Trip date: August 2019
• A AllanMills · 14th October 2019 We had a fantastic time on our recent Tuscan Treats tour. Flavio was our tour guide....however, he is so much more than simply a guide. Flavio is so in love with his country, Italy that you can't help but fall in love with Italy also. Flavio uses his... Show more Trip date: September 2019

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Cinque Terre & Tuscany Walking & Hiking Tour

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• Two distinct and beloved regions of Italy in one amazing trip
• Hike the Cinque Terre's spectacular coastline, with brightly colored cliffside villages
• Outstanding seafood by the Mediterranean and simple hearty fare in Chianti
• Stroll through archetypal Tuscan villages, vineyards and cypress-flanked lanes
• Taste crisp Ligurian white wines and full-bodied Tuscan reds

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En route to pretty Portofino, playground of the rich and famous  A walk along Portofino's postcard-perfect waterfront is a must before heading inland to Chianti.

Vineyards and cypress-flanked lanes  Enjoy the distant views of Siena as you walk from historical Badia a Passignano Abbey to Greve in Chianti, and perhaps shop for local delicacies  A classic Tuscan landscape, with vistas of the medieval hamlet of Montefioralle, spreads out before you Sip regional wines at a fun and informative tasting.

Tuscany's simple hearty fare  Bold balsamic vinegars dance across your tongue in ancient ridgetop Radda, the epicenter of Chianti Classico  Visit Volpaia, a medieval village-turned-winery  Soak up grand pastoral panoramas from the strada bianca (white road), surrounded by vineyards and olive groves.

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Backroads Reviews & Ratings

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Discover the world of active vacations with Backroads. Backroads travel offers engaging trips from bike tours, walking tours and the best family vacations along the back roads. Find the perfect cycling holiday or hiking vacation at Backroads.com. Our Backroads tours range from Grand Canyon hiking to bike trips like Italy cycling trips to multisport vacations like our Costa Rica tours. Enjoy cultural exploration tours, adventures tours and family travel. Singles travel, solo trips and custom trips also available.

With an average tenure of 15 years, our trip designers have the ideal balance of passion, intuition and high-level expertise to create truly remarkable experiences that provide an overall sense of journey while leaving you free to add your own unique imprint. During the hundreds of behind-the-scenes hours that go into crafting each itinerary, we find the right blend of activities to showcase the best of a region, creating a rich tapestry that you can explore as fully as you wish.

Having all been Trip Leaders, they've seen firsthand what guests find most meaningful. Tom Hale works closely with each trip designer, scrutinizing the details to ensure each Backroads experience meets our gold standard for trip design.

A travel experience is not like purchasing a new bike—you can't give it a test ride. You have to be able to trust what the people providing that experience tell you. Unfortunately, we've seen too many examples of companies quietly subcontracting all aspects of their trips to others and seriously limiting the amount of control they have over trip quality.

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Indulge in Italy's Finest Foodie Pleasures During This 9-Day Guided Tour

Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the Vatican Museums, walk the narrow cobblestone streets of Siena to the shell-shaped Piazza del Campo and see the Torre del Mangia, the second-tallest tower in Italy. Visit a family-run olive mill, where a third-generation olive maker will share how its olives become the decadent oil you’ll taste at the mill. In San Gimignano, eat the best gelato in the world - literally. You’ll meet a world champion gelato maestro who will welcome you into his ice cream parlour to indulge in his favorite flavors. Alongside a Local Expert, marvel at the cathedral at the center of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.

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ITALY , ITINERARIES

The perfect tuscany road trip itinerary.

Rolling hills covered in vineyards, and dotted with charming villages is a dream for a road trip. You’re in Tuscany, one of the most glorified regions in Italy. And it undoubtedly lives up to its reputation!

I’ve traveled around large parts of Tuscany and loved every bit of it. It’s surely a region you’ll go back to again and again!

A Tuscany road trip is the best way to explore the region and I’m here to help you with the route so that you get the most out of your trip.

This 10-day itinerary takes you through some of the best places to visit in Tuscany by car, but feel free to mix things up, shorten it, or prolong it with more destinations if you have the time. You can also check out my post with some of the best Tuscan towns here .

Disclosure: This post may contain affiliate links. That means that if you make a purchase through one of those links, I will get a small commission at no extra cost to you.

Table of Contents

Prepare for a Tuscan road trip

Before heading out on a road trip in Tuscany you need to make sure you have all the essentials. You can read my complete road trip packing list here .

Then you’ll need a car and travel insurance.

Since Tuscany is such a popular road trip destination, I do recommend that you book a rental car a good time in advance of your trip so that you don’t risk paying extra for the most expensive cars or even worse, that there are no cars left at all.

Some tips for renting a car in Italy is to consider how much space you’ll need in the car for luggage and how many people you are. It’s always recommendable to have enough space for all your belongings in the boot so that you can leave the car without anything to be seen when you park.

If there is anything in the car that indicates that the boot could be full, there are more chances for anyone breaking into your rental car. And you don’t want that.

Book your rental car here

When is the best time to go on a road trip to Tuscany

You can enjoy road trips to Tuscany all year round, but the spring and autumn are particularly beautiful and the temperatures are pleasant. That said, they’re also the busiest tourist months.

The winter can get cold with temperatures as low as 3-4 degrees Celsius in the hills and usually 3-4 degrees warmer by the coast. In the mountains, you’re likely to get snow. However, daytime temperatures can be much higher in the sun, so I do recommend dressing in layers if you travel to Tuscany in winter.

The hottest summer months are July and August and temperatures can easily hit 30+ degrees Celsius and are best enjoyed where you can cool down in the sea or a pool. But if this is the only time you’re able to go on a Tuscan road trip, don’t let it stop you!

The region is absolutely mesmerizing in summer too and the hills tend to be a little bit cooler. Keep the air-con on in the car and walk in the shade of medieval buildings in quaint Tuscan towns while eating gelato, and you’ll love it nonetheless.

Driving in Tuscany

Driving in Tuscany is absolutely lovely, especially through the mesmerizing countryside. There are only a couple of large roads on this road trip and it’s the motorways connecting Florence and Siena and Florence and Pisa. These are toll roads .

However, if you’re not used to driving on small, narrow roads it might feel a bit overwhelming at first, especially when meeting other cars. Then a smaller car can be a good idea for you so that you feel more comfortable.

One thing that I notice every time I’ve been road tripping in Tuscany is that a few months later, I get a fine sent to me for some traffic infringement that I haven’t been aware of. I’ve got them sent both to Norway when I lived there, and to Spain where I live now. So there is no hiding if you live in Europe.

So take note of the speed limits . In rural areas and small roads, it’s usually 50 km/hr unless other is marked. When it says end of 50 km/hr, usually it goes up to 70 km/hr. There are both fixed and mobile speed cameras, so the best advice I can give you is to drive within the speed limit at all times and if you’re unsure, drive slower rather than faster.

But there are also parking tickets. I do recommend that you always ask a local if you’re allowed to park for free or if you need to pay as well as where and how to pay if you are unsure.

Those things aside, I’ve never had any bad experiences with driving in Italy, let alone Tuscany, and it’s really all about following the rules (even though it might seem that the Italians don’t.)

Tuscany road trip itinerary

This Tuscany road trip itinerary starts and ends at Florence airport, but you can easily start or end it in Pisa airport too, as it’s only an hour away. For each town you’ll stay at, I’ve included a few hotel alternatives with parking for different budgets so that you can choose what fits you best.

The places we’ll cover in this Tuscany road trip itinerary are the following:

• San Gimignano
• Monteriggioni

Day one – Florence

Make sure you read my guide to where to stay in Florence before you go.

The first of your 2 days in Florence , start off with heading up to Piazzale Michelangelo for the iconic city views. There is paid parking there if you come by car, otherwise, take bus 12 or 11 if you’re not walking.

After having a coffee and enjoying the staggering views, leave your car at the hotel if you brought it and head to the Cathedral of Saint Mary of the Flower, known as Duomo di Firenze in Italian. The most prominent landmark in Florence is not to be missed.

Appreciate masterpieces of Michelangelo, Donatello, and other amazing artists in the Opera Duomo Museum and climb the dome for the day’s second winner view.

For lunch, check out the food market, Mercato Centrale, or find a cute restaurant in the old town.

Spend the rest of the day exploring the Uffizi Museum. Among the Renaissance masterpieces, you can expect to see is the Birth of Venus by Botticelli. But you can also admire art from a large number of Italy’s most famous artists as you wander through corridors lined with sculptures and paintings.

The Giardino di Boboli garden is also a must-visit while at the Uffizi. The museum and gardens deserve at least 2-3 hours but if you find that you have spare time, it’s perfect to wander around the streets soaking in Tuscany’s capital city before dinner.

Round off the day with a nice pizza or pasta in a nice restaurant.

If you want to swap out anything on the itinerary for something more adventurous, why not embark on one of the epic cycling tours of Tuscany’s breathtaking countryside with some wine tasting or a Tuscany Vespa tour ?

For affordable luxury, stay at Alfieri Signature Suites – Alfieri Collezione , a short stroll from Ponte Vecchio and Florence’s old town. However, if your budget isn’t quite there, check out Guest House L’Aranceto only a couple of kilometers from the center. This cute guest house has a free bike rental and a bus stop right outside that takes you into the main sights.

Day two – Florence – San Gimignano

After breakfast, start your second day of this Tuscany road trip itinerary by heading to the Basilica di San Lorenzo and the Medici Chapels. The church once used to be Florence’s main basilica and dates back to the year 393.

The highlight is the Medici Chapel where the Medici family is buried. Michelangelo himself built the sculptures of Giuliano and Lorenzo Medici’s tombs in the New Sacristy, which is one of three parts, the others being the Chapel of Princes and the crypt.

You should also explore the Cannon’s Cloister and the Museum of St. Laurence Treasure and Cellar, Donatello’s burial place.

After this cultural visit, have some lunch before it’s time to get the car and head to San Gimignano. But don’t worry, you’ll be back in Florence for the last day of this Tuscany road trip to explore more.

READ MORE ABOUT FLORENCE

• One day in Florence
• Winter in Florence
• Is Florence worth visiting

It takes one hour to drive from Florence to San Gimignano , but if you’re in the city center, you might take a little longer to get out of the city chaos. Drive south towards Siena and follow the signs right towards San Gimignano just before you get to Poggibonsi.

You can either walk around San Gimignano and soak in the medieval town before dinner or stay at a vineyard and drink nice wine and wander in the Tuscan countryside to relax a bit after a couple of culturally rich days in Florence.

If you’re going to spend extra money on one hotel and one experience during your Tuscany road trip, I highly recommend you spend your evening in the countryside surrounded by vineyards tasting the local produce.

Nothing can really compete with that and this is the place to do it! I’ve recommended a place to stay that I loved for just this below and you can take a leisurely walk through the vineyards in the morning to reach San Gimignano in under an hour.

For a true Tuscan experience, stay at Fattoria San Donato in the middle of the vineyards 3,5 km from San Gimignano. You can stay for dinner and as they produce their own organic wine and olive oil, there is no reason to go anywhere else for the night. There’s even an outdoor swimming pool. However, if you prefer staying in the heart of town, try Hotel Bel Soggiorno . For smaller budgets, stay centrally in the historic 1300’s building Locazione Turistica Totti .

Day three – San Gimiginano – Siena

Spend the day exploring the highlights of the medieval hilltop town. For being such a small place, there are a lot of things to do in San Gimignano .

Head into the heart of the historic center to Piazza della Cisterna where you can see an ancient stone wall in the middle of the square, surrounded by medieval houses and towers.

San Gimignano is famous for its towers. Now there are only 14 remaining, a reminder of the once-wealthy community that featured 72 towers built by the patriarch families to show off their wealth.

The highest of the remaining towers is the 54 meters tall Torre Grossa that’s worth a climb to get a bird’s eye view of the village and surrounding vineyards.

Then head to Piazza del Duomo where you find the Duomo di San Gimignano and Palazzo del Popolo where you can admire frescos painted by some of Tuscany’s leading artists.

Finally, make sure you check out the ancient fortress ruins of Montestaffoli which once protected the town from Siena. Also, make time to stroll around the cobblestoned streets and have a nice lunch at one of the restaurants during the day.

When you’ve explored San Gimignano, it’s time to continue your Tuscany road trip to Siena. The drive takes about 45 minutes past Colle di Val d’Elsa and Monteriggioni.

After you’ve settled in at your hotel, go for a stroll in the old town while looking for a nice place for dinner. The cobblestoned streets are super charming at night and bustle with life.

For a serious luxury experience next to Piazza del Campo, stay at the Grand Hotel Continental Siena – Starhotels Collezione . The 5-star hotel is almost like staying in a museum with beautifully decorated walls and ceilings covered in frescos. For a mid-range budget, stay at Hotel Athena and for a budget stay, try B&B La Verbena 3 km outside town or Villa Socini at walking distance from the historic sites.

Day four – Siena

It’s fully possible to see Siena in one day and still leave a bit of time for enjoying a nice lunch at one of Italy’s most famous squares, Piazza del Campo.

The shell-shaped square is home to a few of Siena’s main attractions, like Torre del Mangia, where you can climb the top for a bird’s eye view of the square, The Civic Museum, Palazzo Publico, and the Fonte Gaia fountain.

You can easily explore all of that before lunch and after lunch, you can head to the Duomo of Santa Maria Assunta, Siena’s mesmerizing cathedral where you also can visit the Baptistery of San Giovanni, the Crypt, Museo dell’Opera, and the astounding library, Libreria Piccolomini.

If you have any remaining time before dinner, spend it getting lost in the streets and soak in the medieval feel this amazing town still breathes.

RELATED: Siena from Florence day trip

Day five – Siena – Monteriggioni – Volterra

On day five of this Tuscany road trip, you need to get up early as you’ll be starting the day, after a good breakfast and aromatic Italian coffee, with driving to the walled town of Monteriggioni. The drive only takes 20 minutes and there is a big paid parking lot outside the walls with a short walk up a set of stairs to enter the gates.

Monteriggioni might just be the smallest town in the whole of Tuscany, but that doesn’t mean it’s a grand place to visit and with its proximity to the main road it’s become a popular stopover.

The dramatic history of the fortified town started in 1213 when it was built as a Siena defense strategy to protect the region against the Florentine. From the early 14th century, the Monteriggioni served as the Italian Brotherhood of Assasins’ headquarters. Further, the world-famous video game Assasins Creed is among other Tuscan destinations, set in Monteriggioni.

With this history, it’s hard to pass on this tiny corner of Tuscany. Walk through the town to the main square Piazza Roma, where you’ll find the Romanesque-style church of Santa Maria Assunta. There are also a few restaurants where you can have lunch before continuing on your road trip through Tuscany – or you can wait until you arrive at your next destination.

But before you leave, this unique place, make sure you climb the city walls. There is a small entry fee of 1,50 Euros (at the time of writing) but it’s absolutely worth it.

When you’re ready to leave, you have a 45-minute drive westwards, to the bigger walled town of Volterra .

When you’ve settled in your hotel and had lunch if you didn’t eat in Monteriggioni, head to the Pinacoteca and Civil Museum. Take in the astounding paintings and sculptures from different artists featured in the 15th century Renaissance structure. You’ll also find ancient ceramics and even the Medici coin collection.

The rest of the evening you can wander the streets and find a nice restaurant for dinner and wine.

Stay in the historic center of Volterra at Hotel La Locanda or for lower budgets, check out Chiostro Delle Monache Hostel Volterra set in a 15th-century monastery and only a short walk from the city walls.

Day six – Volterra – Pisa

Start the morning early with a good breakfast and head outside the city walls to see the Teatro Romano, a large archaeological site where you can maze at the remains of a Roman theater dating back to the first century. You should also visit the Parco Archeologico Enrico Fiume to see the remains of a second-century Etruscan Acropolis.

Nearby, you can see the Medici Fortress, though not open to visitors (it’s actually a prison now,) it’s still a unique structure with a dramatic history.

For lunch, head to Piazza dei Fiori where you also find the 13th-century Palazzo Pretorio and the oldest Town Hall in Tuscany, Palazzo dei Priori, built between 1208 and 1257.

After lunch, head to Palazzo del Popolo and visit Duomo Santa Maria Assunta which is a beautiful blend of different architectural styles from different centuries.

The 13th-century baptistery is the most prominent structure in Volterra and stands individually from the cathedral. You can also visit the Diocesan Museum of Sacred Art that’s found in the monastery next to the baptistery.

Before continuing your Tuscany road trip to Pisa, make time to wander the cobblestoned streets of Volterra to soak in the dramatic history that lived in the medieval walls. Make sure you don’t miss out on the Arco Etrusco, and the ancient gate in the walls that was later rebuilt by the Romans.

The drive from Volterra to Pisa only takes about an hour , but if you plan on having dinner in Pisa, you shouldn’t leave it for too late so you get time to get settled at your hotel too.

In Pisa, stay centrally at B&B Di Camilla , a wonderful and homely feel. For lower budgets, check out My Way . It’s a super friendly hotel within walking distance from the Leaning Tower of Pisa – great value for money!

Day Seven – Pisa-Lucca

You’re on the seventh day of your Tuscany road trip and in the city of one of the world’s most famous landmarks, the leaning tower of Pisa. So get up early, have a breakfast of champs, and head to Piazza dei Miracoli and this iconic tower.

On top of taking fun pictures of the tower, make sure you climb to the top. It’s a steep price of 18 Euros, but I’d say it’s a bucket list experience. You can see all updated information about tickets and opening hours on the official website here .

Next to the Leaning Tower of Pisa, you can visit the Cathedral of Maria Assunta, an astounding Romanesque basilica.

Make sure you head to Museo dell’Opera del Duomo to admire impeccable pieces of ancient art such as paintings, sculptures, tombs, and embroideries.

The Sacred Field, Campo Santo, is another great site on Piazza dei Miracoli worth seeing.

The cloister was built towards the end of the year 1200 and has an astounding courtyard lined with beautifully decorated arches.

According to legend, it was built on imported soil from Golotha so that the citizens could be buried in sacred ground. Today, the floor is a mosaic of tombs belonging to Pisan patricians.

After exploring all the sites at Piazza dei Miracoli it’s time for lunch and there are numerous restaurants to choose from. I do recommend removing yourself a little from the square as prices tend to be higher than necessary.

After lunch, it’s time to explore some of the lesser-known yet wonderful attractions in Pisa. The cutest church in Pisa deserves a visit, the Santa Maria della Spina, is a lovely, small Gothic church.

It was actually taken down and rebuilt at the current location in 1871 due to water damage from the river where it used to be.

Head to Piazza dei Cavalieri to maze at the beautifully decorated Palazzo della Carovana and visit the Church of Santo Stefano.

Finally, if you get the time, you should not miss the 10th-century Basilica Romantica di San Pero a Grado. It’s said that St. Peter landed in Italy on the exact spot the basilica is built in the year 44 AD when the Mediterranean reached that far up.

Driving from Pisa to Lucca only takes half an hour , so you can have dinner in Pisa or Lucca as you please.

For a Tuscan feel, stay at the medieval B&B Villa Corte Degli Dei just a short walk outside of Lucca’s city walls. For a charming stay inside the city walls, you can stay at B&B Relais Inn Lucca .

Day eight – Lucca

There are a lot of things to do in Lucca so get ready for yet another jam-packed day of medieval history and intriguing legends. Though you can see Lucca in one day , I’ve left two days to soak in this town as we’re getting close to the end of the Tuscany road trip and you do want to take the time to walk the streets and feel Tuscany when you’re there.

So why not start the day by walking on top of the city walls? This is a popular place for locals to jog or cycle so pay respect when you stop for pictures so you don’t block the road for others.

After your stroll, head to Lucca Cathedral, one of the most unique in Tuscany where all the columns are unique. It’s said that the city held a competition to choose the artist that was going to design the columns, but the citizens couldn’t choose among the finalists, thus they used all the different columns.

Next, get a bird’s eye view of the old town from the top of Torre delle Ore before lunch at one of the restaurants at Piazza dell’ Anfiteatro. The unique square is built on top of an amphitheater that now is buried under the ground. Only some arches are above ground and are incorporated in the pastel-colored, round-shaped buildings shaping the outlines of the structure below.

After lunch, explore the impressive basilicas of San Michele in Foro and Basilica of San Fernando. Then spend some time walking around the cobblestoned streets eating gelato. Maybe you see a nice hidden restaurant where you want to come back for dinner later too.

Day nine – Lucca – Florence

Start the day with an abundant breakfast with an aromatic Italian coffee before heading out to soak in more of wonderful Lucca.

Begin with another startling view of the old town by climbing the 14th-century Guinigi Tower. This is one of the few remaining towers in Lucca from the era when affluent Tuscan families competed to build the highest towers to show their wealth.

You should also explore the Museum of Villa Mansi where you can admire Flemish tapestry collections and other pieces of art. Especially beautiful are the Hall of Mirrors and the Music Hall.

Next, head to Piazza Napoleone where you find Palazzo Ducale di Lucca, a political and administrative center over the last 8 centuries where you can appreciate frescoes and statues.

After lunch, you can either spend a few hours wandering the streets of Lucca or head straight to Florence and wander the streets there.

It’s about an hour’s drive from Lucca to Florence and you might want to return to the same hotel you stayed at last time, or you can check out the options I outlined on day one of this itinerary.

Day ten – Florence

This is the last day of your Tuscany road trip itinerary and you’ll spend it in the incredible capital of Tuscany. After breakfast, I recommend that you go straight to the Ponte Vecchio, one of the most unique bridges you’ll ever see.

Crossing the Arno river, Ponte Vecchio was the only bridge in Florence that survived World War II. Back in the day, it used to be a defense bridge. Now, it’s one of the most photographed sites in Florence. The charming pastel houses with little Mediterranean-style windows look like little dollhouses from afar.

Crossing the bridge, you’ll find lines of jewelry and antique shops competing with art vendors to get tourists’ attention. Once across, you’ll step into Florence old town full of gelato bars (because you HAVE to have more gelato before you leave Tuscany!)

The rest of the day, let yourself get lost in the charming streets of Florence Old Town , eat as much pasta and pizza as you can before you leave, and take lots and lots of photos!

If you would prefer to visit one of the beautiful towns near Florence instead on this last day, you can easily take a day trip from Florence .

Reflections on this road trip in Tuscany

This is by far the best Tuscany road trip with only ten days in my opinion. You get to see the highlights of both larger and smaller towns as well as a couple of days to discover Florence.

If you don’t have a whole week, you can still explore quite a bit of Tuscany on a long weekend break in Italy .

There is no end to the beauty of Tuscany and I really hope you enjoy this road trip through Tuscany as much as I did!

Still haven’t booked your rental car? Make sure you do it straight away so you don’t risk they’re all sold out! Book here .

Heading to Rome next? Make sure you read my complete 4 day Rome itinerary before you go!

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4 thoughts on “ The perfect Tuscany road trip itinerary ”

Love this! I have done 3 road trips in Tuscany and I cannot wait to go again…it is so fantastic! I love your itinerary, I did something very similar the first time and had an amazing trip.

Thank you! I just can’t get enough of Tuscany:)

wow this looks amazing! giving me the travel blues already!

Hopefully you can go soon:)

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My husband and are booked on a five day tour with backroads inTuscany mid-May. The trip was originally a regular cycling/wine trip, but was changed to their dolce tempo style, which means everyone is on e-bikes. We’re not serious cyclists, so perhaps this is for the best. I do ride to work most days, a couple miles each way. What do people generally wear when cycling? Any recent experiences with the Dolce Tempo Tours? Thank you!

2 replies to this topic

I am not an expert on this and have not done any Backroads cycling trips, but I have crossed paths with some of their cyclists while on walking trips in Italy, though since it was a while ago I am guessing they were not on ebikes. The people I saw seemed to be wearing the same type of gear I once saw when staying in a hotel on the Amalfi Coast where professional Italian cyclists in a race were staying -- that bright and tight sort of latex looking stuff. Personally, if I were you I might just wear what you wear cycling at home -- I don't think a vacation is a good time to break in new cycling getups any more than it's a good time to break in new hiking boots. I think you'll also need helmets unless Backroads provides those. Maybe also gloves if that is something you use at home.

Sorry, in my earlier post I meant to say spandex looking stuff, not latex.

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Driving along dirt roads and paths you get to admire the wonderful panorama of the Val d'Orcia.

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The sunset excursion is a unique experience. Walking along dirt roads and paths you arrive at one of the most evocative terraces of Monticchiello to enjoy a good aperitif, with the last rays of the sun illuminating the Val d'Orcia.

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Exploring woods and paths we will arrive near Pienza admiring one of the most enchanting views of Tuscany. Continuing along forest roads, you have the opportunity to contemplate Montepulciano.

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Going along dirt roads and paths we will arrive near the small village of Petroio; continuing the tour, you have the opportunity to do the real off-road. There will be really fun and adrenaline-pumping trial passages.

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After navigating the Montenegrin coastal roads, we decided to cycle inland into mountainous Bosnia-Herzegovina. After a border crossing at almost 1,000 metres above sea level, we descended into a beautiful country with wide plains and empty roads. Enjoying a section of the Ćiro Trail , a former railway route converted into a bicycle path – we enjoyed the spectacular 100-mile journey on the mountain-hugging paved roads into Mostar. The nine-day road trip through Bosnia-Herzegovina was memorable – a juxtaposition of beauty and war – a diverse landscape dotted with a scarred past evident with its landmine signs, gun-shelled houses and verdant valleys. Gwen Sim

Alpine highs on a circular trip from Munich

After a day’s sightseeing in Munich we headed south to Ötztal in Austria. Here we stayed at Hotel Stern for the night then hiked up to Farst at 1,450 metres to take in the views. After that we relaxed at Aqua Dome , floating in its heavenly outdoor pools as the moon peeked behind the mountains. On the next leg, we took the Timmelsjoch high alpine road (May-Oct) and crossed into Italy at nearly 2,500 metres, staying overnight at Albergo Hochfirst , high in the mountains with stunning views. The following day we headed west and entered Switzerland in Müstair , admiring the wonderful Unesco-listed Benedictine Abbey of St John. At Davos, 50 miles further west, we took the Schatzalpbahn funicular railway to 1,800 metres and enjoyed a breathtaking panorama and an invigorating walk. Then we drove along the shores of Walensee and Zürichsee into Zurich, where we visited museums and strolled around taking in Swiss culture, history and architecture. Our final stop before heading back to Munich was at Lindau on Lake Constance, where we sat in a quaint beer garden under chestnut trees, gazing at the soaring Alps on the other side of the lake. Marei

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Rivers and waterfalls, Zagreb to Dubrovnik

Our road trip started in Zagreb, which is great value and still has amazing foodie finds. Our next port of call was the stunning Plitvice Lakes national park, with its waterfalls and forests, before a beautiful 120-mile stretch of road to Skradin, a hidden sailing town gem, and a perfect base for heading out to Krka national park to enjoy more rivers and waterfalls. Next up was Split, where we took in views of the old town from the 12th-century bell tower of St Domnius Cathedral. We also took a relaxing boat trip to Hvar from Split. Back in the hire car we headed 150 miles south to crowded but utterly beautiful Dubrovnik – also a great place for eating out. Sophie

A precipitous drive in Provence

La Garde-Freinet is a well-preserved medieval village with a fascinating history about 10 miles inland from Saint-Tropez. The hairy roads and mountainous terrain have helped the area avoid the tourist saturation of the coast. When I was a teenager, we drove these mountain roads, eyeing the beautiful scenery and trusting my parents’ driving ability to navigate cliff edges and dust tracks. The village is absolutely worth the edgy drive. The beautiful stone houses, the deep chestnut and cork forests and the distant outline of the Alpes-Maritimes will capture any heart. Sarah

South of Naples on the road to Aspromonte

An Italian ice-cream seller told me a less crowded, equally spectacular road trip alternative to the Amalfi coast last summer: the evocatively named Violet Coast road in Calabria. Inspired by his praise, we headed south 260 miles from Naples in our camper – to the Capo Vaticano peninsula on a road of dramatic cliffs on one side tumbling down to soft sandy beaches and sensual cerulean sunsets on the other. I had to concentrate on keeping my eyes on the road so I stopped at the town of Tropea for an energising coffee. I carried on along narrow streets zigzagging their way past ancient castles and villas with the mountains of the Aspromonte national park in the distance until another break at the pretty village of Pizzo. More coffee and a view of the volcanoes of Stromboli (from Tropea) and Etna (from Lazzaro) drew me ever farther south before heading back to Naples via Siderno and Catanzaro. Will

Winning tip: A change of gear, Roscoff to San Sebastián

As one of a group of surfers I took the ferry from Plymouth to Roscoff and drove down the west coast of France to San Sebastián, just over the Spanish border, stopping along the way to surf the amazing breaks and eat some fantastic food. Highlights include the awe-inspiring Dune du Pilat (Europe’s biggest sand dune), eating fresh moules-frites by the port in Hossegor , and chipirons à la plancha (tiny fried squid from the Basque region) with a cold beer watching the sun go down in Guéthary . San Sebastián proved as wonderful as its reputation suggested: a beautiful city full of more gastronomic and architectural delights. Sarah D The last tip was amended on 26 April 2024. The ferry was from Plymouth to Roscoff, not Saint-Malo, as a previous version said.

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