Embark on an unforgettable journey through rolling vineyards, medieval hilltop towns, and the picturesque landscapes of Chianti and Val d’Orcia on this 7-night Tuscany bike tour. Designed for cyclists who love exploration, fine wine, and Italian culture, this Tuscany self-guided bike tour lets you enjoy the freedom of the open road with full support, seamless logistics, and carefully curated routes.
You’ll ride at your own pace through world-famous wine regions, discover charming villages, and indulge in authentic Tuscan cuisine while staying in beautiful hand-selected hotels along the way.
Tour Highlights
- Cycle Through Tuscany’s Most Stunning Landscapes – Ride through rolling vineyards, cypress-lined roads, and olive groves, experiencing the best of Tuscany’s countryside.
- Visit Historic Towns & Villages – Explore Greve, Radda, Castellina, San Gimignano, and Siena, each offering a unique glimpse into Tuscany’s rich history and culture.
- Indulge in World-Class Wine & Cuisine – Taste renowned Chianti wines, handmade pastas, and local specialties at traditional trattorias and wineries along the route.
- Ride at Your Own Pace with Full Support – Enjoy the flexibility of a self-guided tour, with GPS navigation, detailed route notes, luggage transfers, and local assistance whenever needed.
- Stay in Beautiful Boutique Hotels – Each hotel is carefully selected for comfort, charm, and breathtaking locations in the heart of Tuscany.
Who Is This Tour For?
- Cyclists Who Love Leisurely Exploration – This Tuscany bike tour is designed for relaxed riders, with routes averaging 30-50km per day, plus optional longer rides.
- 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.
- Wine & Food Lovers – Ride through Chianti’s famous vineyards, stopping for wine tastings and farm-to-table meals featuring local olive oils, cheeses, and pastas.
- History & Culture Enthusiasts – Explore medieval hilltop towns, Renaissance architecture, and centuries-old traditions in Siena, San Gimignano, and the charming villages of Chianti.
- Travelers Seeking a Balanced Adventure – This tour blends scenic cycling with time to relax, making it perfect for those who want active days and leisurely evenings.
We love customizations, and if you would like to modify the below itinerary please ask us.
See the full itinerary below. Also, to learn more details about our Tuscany bike tours CLICK HERE.
- 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: 8 days, 7 nights
Service: Supported, Private, “Self Guided” tour. GPS Guidance! But your first day is fully guided with a guide! For more about how our Self Guided tours work CLICK HERE.
Type of riding: Rolling to hilly terrain with some climbs.
Bikes suggested: Road bikes, e-bikes, or hybrids
Average daily riding: 30km
Start city: Florence
Finish city: Volterra
Suggested transport: Fly to 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 |
| Greve in Chianti | Albergo del Chianti |  |
| Radda In Chianti | Relais Vignale |  |
| Siena | Hotel Athena |  |
| San Gimignano | Hotel Relais Santa Chiara |  |
| Volterra | Park Hotel Le Fonti |  |
All bikes come with helmet, repair kit, pump (or CO2 cartridges), lock, and water bottles. During the registration process, you will be asked for sizing specifics to ensure we have the correct sized bike waiting for you. We can supply a number of styles of pedals – please ask if you don’t see the pedal type you’re looking for on the registration form.
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$2,945
- Single Occupancy: US$3,645 (for single room occupancy on multiple person tours)
- Solo Tour: Please contact us
Bike Rental Per Person:
- Road Bike: US$425
- eBike: US$425
- Hybrid: US$350
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 Greve in Chianti – 32km/20mi
Your adventure begins in Florence, where you’ll meet your guide for a bike fitting and tour briefing. To help you navigate the busy city streets, your guide will ride with you out of Florence, leading the way into the stunning countryside of Chianti.
Once beyond the city, enjoy a peaceful 32km ride through rolling vineyards and olive groves, arriving in Greve, a charming market town known for its Chianti wines and lively central piazza. Your luggage will be waiting for you at the hotel, so after checking in, take some time to explore. Perhaps enjoy a wine tasting at one of the local enotecas before settling in for an included welcome dinner.
Day 2: Greve in Chianti to Radda – 30km/19mi
Today’s ride takes you deeper into the heart of Chianti, cycling along quiet country roads toward Radda, a beautiful hilltop village with breathtaking views.
On the way, stop in Castellina, a town with an Etruscan history, stone-paved streets, and panoramic terraces. If you want a bit more time in the saddle, an optional 20km extension allows for extra exploring.
Arrive in Radda, where you’ll check into your hotel and enjoy a relaxing evening with a delicious included dinner.
Day 3: Radda in Chianti to Siena – 33km/21mi
Today’s ride is a gentle and scenic 33km route, taking you through Tuscan vineyards, medieval hamlets, and rolling countryside on your way to Siena.
A stunning city known for its well-preserved medieval architecture and famous Piazza del Campo, Siena is a must-visit destination. Stroll through its narrow alleys, visit the breathtaking Duomo, and immerse yourself in its rich history.
Dinner is on your own tonight, giving you the perfect opportunity to discover Siena’s fantastic local restaurants—don’t miss out on the region’s signature dish, pici pasta with wild boar ragu.
Day 4: Explore Siena (Optional Loop Ride Available)
Today is a rest day designed for you to fully experience Siena. Wander through its cobblestone streets, visit the grand Palazzo Pubblico, and shop for local delicacies like pecorino cheese and Tuscan olive oil.
If you’d like to keep riding, your guide can suggest a scenic loop route around Siena, offering more chances to soak in the region’s beautiful landscapes.
Dinner is on your own, so explore Siena’s charming trattorias at your leisure.
Day 5: Siena to San Gimignano – 41km/25mi
Leaving Siena, you’ll ride through some of Tuscany’s most postcard-perfect countryside, heading toward the medieval wonder of San Gimignano.
Along the way, stop in Colle di Val d’Elsa, a town famous for its beautiful crystal glassware and historic old town. As you approach your destination, you’ll see why San Gimignano is called the “City of Towers”—its medieval skyline is one of the most iconic in Italy.
Your hotel is located near the historic center, making it easy to explore this UNESCO-listed town. Dinner is included tonight at a local restaurant, where you can enjoy a classic Tuscan meal with a glass of Vernaccia wine, unique to the region.
Day 6: Explore San Gimignano (Optional Loop Ride Available)
Today is another flexible day to explore at your own pace. Take in San Gimignano’s stunning medieval streets, artisan shops, and panoramic views. Don’t forget to visit Piazza della Cisterna for a scoop of world-famous gelato!
If you’re up for another ride, work with your guide to plan an optional cycling route through the surrounding vineyards and rolling countryside.
Dinner is included tonight at your hotel, giving you time to unwind and enjoy the peaceful atmosphere of this historic town.
Day 7: San Gimignano to Volterra – 32km/25mi
Your final ride takes you further into Tuscany’s wilder, more rugged landscapes, as you head toward Volterra, one of the region’s most historically rich and picturesque hilltop towns.
Set atop dramatic cliffs, Volterra boasts an incredible Etruscan and Roman history, with ancient city walls, a stunning Roman theater, and charming streets lined with artisan shops.
After checking into your hotel, explore the town’s historic center or relax at a local café with a glass of Tuscan red wine. Your rental bike will be collected today.
Dinner is on your own tonight, giving you the perfect chance to discover Volterra’s incredible culinary scene.
Day 8: Departure from Volterra
After breakfast, say goodbye to Tuscany as you prepare for your next adventure. Frequent buses connect Volterra to local train stations, making travel to Florence, Pisa, or beyond seamless. We’re happy to assist with travel arrangements to make your departure stress-free.
