Classic Tuscany - Cycling Florence to Pisa
Bike - Self-Guided Tour
Overview
The best way to explore one of Italy's most famous regions, Tuscany, is to cycle through it while enjoying the perfect blend of culture, cuisine, history, and rolling scenery. Tuscany is known for its earthy wines, rich art history, architecture, and its welcoming people. From Piazza della Signoria in Florence to Piazza dei Miracoli in Pisa, you will cycle through living history, also stopping in Siena, San Gimignano, and Lucca. This bicycle tour starts in the heart of Tuscany along the Chianti "wine route", followed by an endless number of wine valleys where you can visit a local winery. After magnificent Siena our bicycle tour continues to San Gimignano, famous for its adorning towers, and Lucca, known for the well-preserved Renaissance walls encircling its historic city center. Lastly, you'll visit Pisa and its leaning tower. Join us and experience Tuscany by bicycle.
Highlights
- Rennaissance Florence
- The Chianti wine region
- Marvelous Siena
- Monteriggioni, San Gimignano
- Vinci, the home of Leonardo
- Sleep in an agriturismo farm estate
- Lucca, ride on Europe's best preserved medieval walls
- Cycle to Pisa, the famous Leaning Tower
Daily itinerary
Day 1 Day 1 - Arrive in Florence
Highlights: Renaissance Florence, Uffizi Gallery
Arrive in Florence today and take in the city's rich history and its beauty: climb up Giotto's tower for a stunning view of the city below and the Duomo in the skyline; visit the Uffizi Gallery, or walk the Ponte Vecchio bridge for a striking angle. We will meet in the afternoon for a tour briefing and bike fitting, and give you suggestions for dinner.
Accommodation: Hotel Silla, or similar. Upgrades available - please inquire for details
Day 2 Day 2 - Florence to Radda in Chianti
Highlights: The Chianti region
As you leave Florence you will climb some of Chianti's famous hills, on your way to Radda in Chianti, your home for the night. Stop in Greve for a visit of the main square and the famous Macelleria Falorni, producer of local salumi (cold cuts). Radda is a delightful a small town and was historically an important junction for traveler's heading to north and south.
Daily distance: 61 km (38 miles)
Elevation gain: +1230m (4052ft)
Terrain Type: Hilly
Accommodation: Hotel San Niccolo, or similar. Upgrades available - please inquire for details
Day 3 Day3 - Cycle to Siena
Highlights: Medieval town of Siena, Piazza del Campo
Cycle the south part of the Chianti Region, then take the afternoon to explore Siena. Italy's best-preserved medieval city rivaled Florence for dominance in Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls.
Daily distance: 52km (32 miles).
Elevation gain: +958m (3143ft).
Terrain Type: Hilly
Accommodations: Hotel Il Chiostro del Carmine, or similar. Upgrades available - please inquire for details
Day 4 Day 4 - Ride to San Gimignano
Highlights: The jewel village of Monteriggioni, San Gimignano
Your bike ride today takes you into the heart of Tuscany. You will pedal past vineyards, 17th century villas, and small towns on your way to San Gimignano, one of the best-preserved medieval villages in Italy and designated a UNESCO World Heritage Site. San Gimignano is famous for its many towers, remnants from the 13th and 14th centuries.
Daily distance: 52 km (32 miles).
Elevation gain: + 895m (2936ft).
Terrain Type: Hilly
Accommodation: Hotel Leon Bianco, or similar. Upgrades available - please inquire for details
Day 5 Day 5 - From San Gimignano to Vinci
Highlights: Olive groves and vineyards, Leonardo da Vinci's birthplace and museum
Our ride takes you through rolling hills peppered with small towns along the way. Your final destination is Vinci, the birthplace of Leonardo da Vinci. Here you'll have a chance to visit the house where da Vinci was born and a museum with scale models of his inventions.
Daily distance: 72 km (45 miles).
Elevation gain: + 1021m (3050ft).
Terrain Type: Hilly
Accommodation: Agriturismo il Piastrino, or similar. Upgrades available - please inquire for details
Day 6 Day 6 - Bicycle to Lucca
Highlights: Medici villa, bicycle countryside of Tuscany, 17th century wall
Climb the stairway to the Medici villa in Cerreto Guidi today for a great view as you continue west to Lucca, where you'll stay the next two nights. Lucca was a Roman town and one of medieval Italy's most prosperous city-states. Today, Lucca retains its medieval charm with its small shops and sidewalk cafes, as well as the beautiful 17th-century wall surrounding the town.
Daily distance: 59 km (36 miles).
Elevation gain: + 438m (1437ft).
Terrain Type: Rolling Hills
Accommodation: Hotel La Luna, or similar. Upgrades available - please inquire for details
Day 7 Day 7 - Loop ride to Pisa
Highlights: Leaning Tower of Pisa, Piazza of Miracles, Lake Massaciuccoli
Your last day of cycling takes you to Pisa where you can visit the Leaning Tower and the Piazza of Miracles (arriving there by bike is a grand experience!). Our route to Pisa takes you by Lake Massaciuccoli, where Puccini wrote many of his operas. After a stroll through Pisa, head back to Lucca to enjoy an evening "passeggiata" along the main pedestrian way, or explore its countless amazing alleys and piazzas.
Two options for your ride today - cycle to Pisa and return by train (with bike aboard). Or a longer loop ride, through lovely Tuscan hills, vineyards and stately villas. If you are up for the challenge, add an out and back ride all the way to the Tuscan coast and dip your toes in the Tyrrhenian Sea!
Short option (cycle to Pisa, return to Lucca by train): 31 km (19 miles), with + 143m (470ft) Elevation gain - Terrain type mostly flat.
Long option 1: 61 km (37 miles), with + 367m (1205ft) Elevation gain - Terrain type mostly flat.
Long option 2: 77 km (48 miles), with + 527m (1729ft) Elevation gain - Terrain type rolling hills.
Extra ride to the coast: additional 29 km (18 miles), with 108m (350ft) Elevation gain.
Accommodation: Hotel La Luna, or similar. Upgrades available - please inquire for details.
Day 8 Day 8 - Tour ends
Highlights: Arrivederci!
After a breakfast buffet in your hotel, you're ready to continue your adventure wherever it may lead. We hope you have enjoyed cycling with us! Thanks for joining us and "buon viaggio"!
PLEASE NOTE: The final itinerary, including hotels and/or activities described here, are subject to changes according to availability.
Difficulty description
You will ride mostly on hilly terrain, with some good climbs, average daily elevation gain of about 800m (2600 feet). Few longer days aslo make this tour enjoyable by experienced cyclists, confident with some hard-packed gravel roads and prefering bikes with wider tires.
Visit our Tour difficulty level page to learn more about terrain levels and how we determine day and tour levels.
Map
What's included
- 7 nights in 3- and 4-star hotels
- All breakfasts
- Luggage transfers
- All Classic self-guided tour inclusions
Optional activities
- Cooking classes available in various tour locations! Organized by Le Cesarine, experts in Italian culinary experiences. You will be hosted by a local at their home - your "Cesarina" - in a class that lasts about three hours, during which you will help the Cesarina prepare three courses. In the fourth and final hour, you will enjoy the meal (lunch or dinner) which you prepared during the class. Water and one bottle of house wine for every 3 people are included.
- Guided visit of Florence
- Guided visit of Siena
- Wine tasting in Vinci (closed on Monday)
- Dinner in Vinci
Dates and availability
This tour is available between March 1 and October 31
Starts every Friday. Other start days available by request (extra fee applies). Please note that starting on certain days of the week will make some visits (such as museums or tastings) impossible. Most museums in Florence are closed on Mondays, so we discourage starting tour the previous Monday.
2025 Confirmed departure dates:
Coming soon (please inquire!)
________________________________________
If you are looking for challenging cycling in Tuscany, our Postcard Southern Tuscany tour (8-day) can also be done back to back with this tour for a Grand Tour of Tuscany! Don't want to break a sweat but still explore this amazing region? You can with our top-notch e-bikes!
________________________________________
Tour Code: itbs3564
Prices
Low season: €1495
2025 dates: Mar 1 - Apr 31; Jun 16 - Aug 31; Oct 15-31
High season: €1595
2025 dates: May 1 – Jun 15; Sep 1 - Oct 15
Prices per person, based on double occupancy; minimum 2 participants per departure.
Single supplement: €325 (in double room for single use)
Solo traveler departures: €925 (only one person on the departure). Includes the single/double room supplement and a GPS unit with the pre-loaded routes.
Lodging upgrades & extra nights are available: please inquire
City hotel tax not included in tour package (2 to 5 euro per night per person, to be paid locally by traveler).
* due to the 2025 Rome Jubilee, some cities may charge a higher per night tax
GPS device rental, as well as a printed roadbook, are available at an optional extra fee:
- GPS device rental: €50
- Printed roadbook: €45 (second copy of printed roadbook €15)
See the What's Included section for details on included navigation tools
Group Discounts are available for participants booking together on the same departure! Please inquire!
For more ways to save, see our discounts and promotions page.
Bike rental
Bike Rental options:
We offer quality bikes in different styles, all great options for this bike tour. Our bikes are maintained and delivered in optimal working condition.
The prices below are per bike for the duration of the tour, including delivery to starting point in Florence and collection from ending point in Lucca.
Bike rental rates
Aluminum hybrid: €160
Premium Titanium road or hybrid: €200
Touring E-bike (hybrid with straight handlebar): €280
Tandem: €295 (priced per bike, for 2 cyclists)
Tag-along or kid trailer: €80
Bike rental insurance is available for purchase with all our rental bikes – see details in the Bike Rental Insurance section of our Terms and Conditions page.
For detailed specs and photos of our bikes, see our website - Bike Rentals Italy.
Trip planning
Starting point
Starting point: Hotel Silla - Via de' Renai, 5, Firenze
We recommend flying into Florence Airport (FLR) , but you can also fly into Pisa Galileo Galilei Airport (PSA)
- It’s a 30-minute trip from the airport to Florence’s main train station Firenze S. Maria Novella. You can catch a shuttle bus, or take a bus
- If you'd rather take a taxi, agree on a fare before accepting the ride. It takes about 15/20 minutes, depending on the traffic
The meeting time for our self-guided tours is typically set between 2pm and 4pm. We recommend travelers plan accordingly allowing plenty of time to arrive at the determined meeting place. Please note a late fee may be applied for late arrivals - please see our terms page for details
Ending point
Ending point: Hotel La Luna - Via Fillungo, Corte Compagni, 12, Lucca
We recommend flying out of Pisa Galileo Galilei Airport (PSA), but you can also fly out of Florence (FLR), Rome Fiumicino (FCO), or other Italian airports
Airport transfers:
- Taxis from Lucca to the Pisa airport take about 45 minutes
- From the hotel, take a taxi (5-minute ride) to the Lucca train station. Pisa International Airport Galileo Galilei is 45 minutes away: once you arrive in Pisa centrale train station, you will find the PisaMover monorail to get to the Airport in 5 minutes
Private airport transfers available if you prefer to be driven from airport to hotel in a private vehicle transfer, please inquire for cost - we will be happy to include this service in your tour package
Final arrival and departure instructions along with other detailed pre-travel documents, will be e-mailed prior to your travel, with information specific to your departure (including the actual hotels used on your tour dates, which may vary from the hotels listed above.)
Photo gallery
Customer reviews
Click to read past traveler reviews
This particular tour is for reals. It is not for anyone who hasn’t specifically trained to do 40 miles and 3000 feet of climbing day after day. But if you are a serious cyclist, it is great. We got to see so much of the countryside and stay in cool towns we likely never would have. Radda, San Gimignano, and Lucca were particularly good. It was fun to ride through the city gates, get food and drinks, and do a little shopping each day (not much in Radda).
- Becky J. (USA, 2023)
We wanted a trip in Tuscany that would allow us to balance riding and touristing. We also needed a route that would be challenging for two cyclists and acheivable for one on an eBike. We didn't realize how good the RideWithGPS information and maps would be. As soon as we saw them, we realized the printed roadbook is completely unnecessary and I think they could be completely removed. Everything was spectacular. The hotels are great, the routes are great, and the service made the whole trip easy. This was one of our best vacations. Everything that Cycle Europe provided worked great and made it an easy trip, so we could simply enjoy ourselves.
- Jeff B. (Canada, 2023)
We absolutely loved our custom-built self-guided tour ! We had some minor issues with the ebikes but the issues were quickly resolved when we contacted Igor for support. Hotels / breakfasts / staff at each hotel were all awesome! Everything was well planned / supported / easy to do / probably our favorite part of our Italy experience/ pre booked hotels with baggage delivery. Our favorite: the scenery / the adventure/ each town we visited / the people we met / the good and wine !!!
- Coleen S. (Canada, 2022)
10 out of 10: We really appreciated Sara Lettereli's help throughout planning, orientation, and the trip itself. (Our favorite part was) experiencing the culture of Tuscany and its people and rich history, architecture, art, agriculture, landscape and food.
- Tom H. (USA, 2021)
10 out of 10: Excellent customer service. We started out working with a few different outfits, but Sara Letterelli was by far the most responsive contact we had. She was able to meet all of our picky requests and kept us informed throughout the whole process. Beautiful scenery and fun cycling. Thank you for a most wonderful and memorable trip!
- David M. (USA, 2022)
Really a great route and strong package of maps, etc were provided. It was a great experience and I look forward to another trip. Loved Radda.
- Anonymous traveller (2018)
"What was your favorite experience on this trip?" The cities we stopped in and the people we met. Family meal in Vinci especially pleasant.
- Bob L. (USA, 2018)
The step by step directions were perfect. They were exactly on-spot and got us to our destinations. The hotels were great for the level we chose. We especially liked the hotel in San Gimignano with the balcony that overlooked the valley. Very nice! It all was wonderful. Of course the biking was the favorite, especially the routes out of Florence to Radda. Our tour advisor, Stefania, was outstanding! She created this special tour based on the dates and locations and sites we wanted to see. She gave us travel tips for cities that were before and after our tour. She gave recommendations for guided tours in Florence that was outstanding. She earned our confidence in your company as we planned the details together many months in advance. The bikes, the route and the hotels were perfect. The luggage arrived just as planned each day. The weather was even perfect! Thank you Stefania!
- Brent P. (USA, 2017)
