Experience the best of cycling in Tuscany on this 8-night self-guided bike tour, designed for those who love scenic countryside, charming medieval towns, and world-class Italian cuisine and wine.
From the Renaissance heart of Florence to the hilltop splendor of Cortona, you’ll cycle through rolling vineyards, historic villages, and breathtaking landscapes, all while enjoying the freedom of a self-guided tour with full support.
This itinerary blends leisurely rides with cultural immersion, offering plenty of opportunities to taste local wines, explore charming piazzas, and experience authentic Tuscany at your own pace.
Tour Highlights
- Scenic Cycling Routes – Ride through vineyard-covered hills, medieval towns, and stunning Tuscan landscapes on a mix of gentle rolling roads and scenic climbs.
- Explore Tuscany’s Most Beautiful Towns – Visit iconic destinations like San Gimignano, Siena, Montalcino, Montepulciano, and Cortona.
- Savor World-Class Wine & Cuisine – Enjoy Chianti, Brunello, and Vino Nobile wines, plus authentic Tuscan meals at local farmhouses and trattorias.
- Stay in Charming Boutique Hotels – Experience handpicked accommodations in historic town centers and countryside farmhouses.
- Self-Guided Freedom, Fully Supported – Enjoy the flexibility of a self-guided tour, complete with GPS navigation, luggage transfers, and local assistance if needed.
Who Is This Tour For?
- Cyclists Who Love Culture & History – If you enjoy exploring medieval towns, UNESCO sites, and ancient hilltop villages, this tour is for you.
- Food & Wine Lovers – Experience Tuscany’s most famous wine regions, including Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano.
- Intermediate-Level Riders – This tour is best for cyclists comfortable with rolling terrain and daily distances of 40-60km.
- Couples and Small Groups – Whether you’re looking for a romantic cycling getaway or an adventure with friends, this tour offers a mix of independence and guided support.
- Travelers Who Appreciate Boutique Accommodations – Stay in beautiful hotels, historic farmhouses, and centrally located town stays for an authentic experience.
See full itinerary below. Or click here to learn more about our other Tuscany bike tour offerings.
- General Details
- Guide/Concierge Info
- Accommodations
- Rental Bikes Available
- Inclusions
- GPS Availability
- Pricing
- Register For This Tour
Dates: Your pick! We offer tours in Tuscany as early as March and as late as October and into November.
Length: 9 days, 8 nights
Service: Supported, Private, “Self Guided” tour. GPS Guidance! But your first day is FULLY GUIDED with a local guide riding with you! For more about how our Self Guided tours work CLICK HERE.
Type of riding: Rolling & hilly terrain.
Bikes suggested: Road bikes, e-bikes, or hybrids
Average daily riding: 55km
Start city: Florence
Finish city: Volterra
Suggested transport: Fly into Florence (FLR) or by train from anywhere.
From greeting guests when they arrive, to personally handling luggage transfers, to curating excursions, to problem-solving (e.g., flat tires and other unforeseen issues) our concierges assist guests daily. They also set you up on your rental bikes, and can help with routing and simple questions. Need help finding a good lunch spot? Is it raining too hard or you’re too tired to continue? The concierge is a phone call away and are there to help you! Each tour group works with a single, dedicated concierge who can be called upon for in-person assistance at any time.
Over the years we have developed relationships with many amazing 3 and 4-star properties that distinguish themselves as providing much more than their rating suggests. We have loved getting to know these hotels and sharing them with our guests. For tour groups wishing to upgrade their accommodations, we can provide custom pricing for four and five-star hotels, pending availability. Below are an example of some of our favorite hotels in the region that we target using on our tours, pending availability.
| Location | Hotel | Photo |
| Panzano in Chianti | Villa Le Barone |  |
| San Gimignano | Hotel Relais Santa Chiara |  |
| Siena | Hotel Athena |  |
| Montalcino | Hotel Vecchia Oliviera |  |
| Montepulciano | Relais Ortaglia |  |
| Cortona | Hotel Villa Marsili |  |
Road Bikes: Our rental road bikes are a racing style with drop handlebars.
- Type – Full Carbon Road Bikes
- Sizes – 50, 53, 55, 58, 61
- Components – Mixture of Shimano components with a compact double crankset.
Hybrid Bikes: Our rental hybrid bikes are a relaxed style with flat handlebars.
- Type – Hybrid
- Sizes – XS, S, M, L, and XL
- Components – Mixture of Shimano road and mountain components with a triple crankset.
eBikes: These semi-powered bikes allow for non-riders to share the experience with their friends and family who are stronger cyclists.
- Type – eBike
- Sizes – S, M, L
- Components – Mixture of eBike components and Shimano Altus.
During the registration process you will be asked for specifics to have the correct sized bike waiting for you. We can supply any number of styles of pedals – SPD, SPD-r, flat, Speedplay, Look, etc.
- All hotel accommodations – mostly 3 and 4 star but ask for custom accommodation requests.
- An OBT cycling jersey!
- The use of a Garmin Touring GPS during the tour for worry-free routing.
- Detailed route notes, maps, and tourist information. This includes standard cue sheet, and GPS courses to upload to your own GPS device.
- Luggage transfers from hotel to hotel.
- Meals as explained in the tour itinerary pages. Usually this means all breakfasts, no lunches, and some dinners.
- Access to your personal guide/concierge (See Guides/Concierge tab).
WHAT IS NOT INCLUDED:
- Transportation to start location and from finish location.
- Bikes, but we have rental bikes available.
- Travel and Health Insurance.
- Admission to sightseeing venues, unless explicitly mentioned as included.
At the beginning of your tour your local guide will show you how to use the unit. We will also provide instructions that you can reference when needed. As a backup and supplement to the GPS, we will also provide a local map as well as routing instructions.
One unit will be provided to each four guests. If you need additional units they will cost $125 per unit per tour for rental.
Tour Cost Per Person:
- Double Occupancy: US$3,545
- Single Occupancy: US$4,195 (for single room occupancy on multiple person tours)
- Solo Tour: Please contact us
Bike Rental Per Person:
- Road Bike: US$390
- eBike: US$390
- Hybrid: US$295
Questions: First, please feel free to ask us any questions about the tour. We are happy to help clarify any details.
Registration: Once you are ready to register please go to https://outfittertours.com/registration/ and complete the registration form. EACH tour participant will need to complete the form. At the end of the registration for you will be asked for a US$800 deposit. You can pay the deposit by bank check, wire, or credit card. Once we have all registrations we will secure all of the details of your tour – hotels, bikes, etc.
Final Payment: 60 days prior to your tour we will invoice you for the balance of the tour.
Tour Packet Delivery: Once the balance is paid and approximately 30 days before your tour we will send you a complete tour packet containing all details of your tour – accommodation information, detailed routing, a suggested packing list, maps, tourist guide, and much much more!
For more information on our Terms & Conditions please CLICK HERE.
Daily Itinerary:
Day 1: Florence to Panzano – 49km/30mi
Meet your guide in the heart of Florence, a city renowned for its art and architecture. After getting properly fitted for your rental bike, your guide will lead you through the bustling streets of Florence, navigating traffic while sharing insights into the city’s history. Soon, you’ll leave the city behind and start your scenic ride into the Chianti region.
The 49 km route will take you through rolling hills and picturesque vineyards to reach Panzano, a charming hilltop town. After checking into your hotel, enjoy some relaxation time by the pool or explore the town. Your luggage will already be waiting for you, so you can enjoy the famous Chianti wine before your included dinner.
Day 2: Panzano to San Gimignano – 41km/25mi
Today’s ride takes you along small, rolling backroads, winding through olive groves and vineyards, to San Gimignano, known as the “City of Towers.” The town’s medieval architecture and iconic skyline will transport you back in time. You’ll be able to stroll through narrow streets, explore shops selling local goods, and take in stunning views of the surrounding countryside.
Your hotel will be in the heart of this UNESCO World Heritage town, and you’ll have time to explore before enjoying your included dinner.
Day 3: San Gimignano Rest Day or Volterra Loop – 60km/37mi
Take a well-deserved rest day in San Gimignano, where you can wander through the cobblestone streets, shop for local souvenirs, or relax in one of the town’s charming cafes.
Alternatively, if you’re up for more cycling, enjoy a 60km loop ride to Volterra, another historic hilltop town filled with Roman ruins, Etruscan artifacts, and lovely shops. Dinner is on your own tonight, so you can explore the local culinary scene and choose your favorite spot.
Day 4: San Gimignano to Siena – 61km/38mi (shorter 41km/25mi option available)
Today’s ride will take you through picturesque Tuscan landscapes along traffic-free backcountry roads, leading you to the beautiful city of Siena. As one of the most famous cities in Tuscany, Siena offers stunning medieval architecture and rich history. You have the option of taking a shorter 41km route if you prefer a more relaxed pace.
Once in Siena, check in to your hotel, located just inside the town gates. Spend the rest of the day exploring Siena’s historic landmarks, including the Piazza del Campo and Siena Cathedral. Dinner is on your own tonight—take your time to discover the many excellent restaurants in the area.
Day 5: Siena Exploration
Enjoy a day off the bike to explore Siena at your leisure. Take in the medieval architecture, do some shopping in the quaint shops, or relax in one of the town’s beautiful piazzas. Siena is famous for its culinary delights, so you might also want to sample some traditional Tuscan dishes.
Dinner is again on your own tonight—ask your guide for recommendations or try one of the many local trattorias.
Day 6: Siena to Montalcino – 53km/33mi
Leave Siena behind as you ride on small backroads with incredible views of the Tuscan countryside. Pedal through the rolling hills toward Montalcino, a hilltop town known worldwide for producing Brunello di Montalcino wine.
After checking in to your hotel, take time to explore the town and enjoy its quaint streets, then choose from the many fine wine bars or restaurants for dinner. This area is perfect for wine lovers, so indulge in a glass of the local Brunello paired with a delicious meal.
Day 7: Montalcino to Montepulciano – 40km/25mi
Today’s ride takes you from Montalcino to Montepulciano, a 40km journey through the rolling hills of Tuscany. If you’re feeling adventurous, there are options to extend the ride with a few extra hills, giving you a chance to experience more of the scenic countryside.
On your way, you’ll pass through Pienza, a lovely town perfect for a lunch stop and some exploration. Dinner is on your own tonight—explore the town and choose from a variety of local eateries.
Day 8: Montepulciano to Cortona – 53km/33mi
Today, you’ll head into Umbria, cycling towards Lake Trasimeno. Your ride takes you downhill to the beautiful village of Castiglione del Lago, where you can stop for a lovely lunch overlooking the lake. From there, continue to Cortona, a hilltop town famous for its Etruscan history and stunning views.
After checking into your hotel, spend your last evening in Tuscany exploring the charming streets of Cortona. For a special treat, consider dining at Il Falconiere, a Michelin-starred restaurant just outside the town. Dinner is on your own tonight.
Day 9: Cortona Departure
After breakfast, it’s time to say goodbye to Tuscany. You can take a train from the local depot to your next destination, or we can assist with arranging your travel back to Florence or another location.
