This is one of our most popular itineraries! Discover the breathtaking landscapes, world-class wines, and historic towns that make cycling in Tuscany an unforgettable experience. This Tuscany Self-Guided Bike Tour is designed for riders who want a relaxing yet immersive adventure, with the freedom to explore at their own pace while enjoying the comforts of charming accommodations, luggage transfers, and expert local support.
Ride through the rolling vineyards of Chianti, explore the medieval streets of Siena, and take in the iconic skyline of San Gimignano, and beyond—all while experiencing the best of Tuscany by bike.
Tour Highlights
- Scenic Tuscany Bike Routes – Ride through Chianti vineyards, medieval towns, and rolling countryside with quiet backroads and spectacular views.
- UNESCO World Heritage Sites – Visit Siena and San Gimignano, two of Italy’s most beautiful historic towns.
- Authentic Tuscan Cuisine & Wine – Enjoy included dinners in Radda, San Gimignano, and Volterra, plus opportunities for wine tastings and local specialties.
- Self-Guided Freedom with Full Support – GPS navigation, detailed maps, luggage transfers, and expert local assistance ensure a seamless journey.
- Charming Accommodations – Stay in handpicked boutique hotels, each offering an authentic and comfortable experience.
Who Is This Tour For?
- Cyclists Who Love History & Culture – If you enjoy exploring medieval towns, visiting UNESCO sites, and immersing yourself in local traditions, this tour is for you.
- Wine & Food Enthusiasts – Savor Tuscan wines, farm-to-table cuisine, and world-famous gelato along the way.
- Riders Who Enjoy Rolling Terrain – Expect moderate daily distances (30-50km) with some hills, making it ideal for intermediate riders who love a challenge but still want time to relax.
- 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 Value Comfort & Flexibility – Enjoy boutique accommodations, luggage transfers, and self-guided independence, while still having local support when needed.
See full itinerary below. Or please click here to learn more about our other Tuscany bike tours.
- 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: 7 days, 6 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: Florence
Suggested transport: Fly in 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 |
| 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 |  |
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$2,745
- Single Occupancy: US$3,195 (for single room occupancy on multiple person tours)
- Solo Tour: Please contact us
Bike Rental Per Person:
- Road Bike: US$350
- eBike: US$350
- Hybrid: US$260
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
Your journey begins in Florence, where you’ll meet your local guide for a bike fitting and route briefing. You guide will ride with you through the iconic streets of Florence, navigating the city and then heading into the stunning Chianti countryside.
Pedal through vineyard-covered hills and quiet backroads as you make your way to Panzano, a charming hilltop town known for its Chianti wines and breathtaking views.
Upon arrival, check into your hotel, where your luggage will be waiting. Relax by the pool, sip a glass of Chianti Classico, and take in the sunset over the vineyards before enjoying an included welcome dinner featuring authentic Tuscan flavors.
Day 2: Panzano to San Gimignano – 41km/25mi
Today’s ride takes you to one of Tuscany’s most famous towns—San Gimignano, the City of Towers. Cycle through rolling hills, past olive groves, and medieval villages, with plenty of opportunities to stop for photo-worthy views and local wine tastings.
Arrive in San Gimignano, a UNESCO World Heritage site famous for its medieval skyline and world-renowned gelato. After checking into your hotel, explore the cobbled streets, artisan shops, and historic piazzas before enjoying an included dinner in the heart of town.
Day 3: San Gimignano to Siena – 61km/38mi (or shorter 41km/25mi option)
Today’s ride offers two options: a challenging 61km route through Tuscany’s rolling backroads or a more relaxed 41km ride with equally stunning scenery.
Your journey culminates in Siena, one of Italy’s most beautiful medieval cities. Ride through vineyards, cypress-lined roads, and historic villages before entering Siena’s UNESCO-listed historic center. Check into your hotel, located inside the town gates, allowing you to easily explore Siena’s winding streets, stunning Duomo, and famous Piazza del Campo.
Dinner is on your own tonight—take the opportunity to discover Siena’s renowned cuisine, perhaps trying pici pasta with wild boar ragu at a traditional trattoria.
Day 4: Siena to Montalcino – 53km/33mi
Depart Siena along scenic quiet roads with stunning city views, heading south toward Montalcino, home of the world-famous Brunello wine.
The rolling terrain offers panoramic vistas, charming farmhouses, and picturesque villages before you arrive in Montalcino, a medieval hilltop town surrounded by vineyards and fortresses. After checking into your hotel, take time to visit a local winery, explore the historic fortress, or simply relax with a glass of Brunello.
Dinner is on your own tonight, allowing you to choose from Montalcino’s many excellent restaurants—from wine bars to Michelin-starred experiences.
Day 5: 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 6: Montepulciano to Cortona – 53km/33mi
Your final ride takes you across the border into Umbria, offering spectacular views of Lake Trasimeno.
The route is mostly downhill toward Castiglione del Lago, a charming lakefront town with historic streets and fantastic lunch spots. From here, continue to Cortona, a stunning hilltop town known for its Etruscan history, breathtaking views, and rich culture.
Check into your centrally located hotel, giving you easy access to Cortona’s museums, churches, and excellent dining options.
Dinner is on your own tonight, and we highly recommend Il Falconiere, a Michelin-starred restaurant located just outside town, offering a spectacular final meal to celebrate your cycling adventure.
This evening, your rental bikes will be collected, marking the end of your journey.
Day 7: Departure from Cortona
After breakfast, depart Cortona by train. Frequent connections make it easy to reach Florence, Rome, or your next destination. We’re happy to assist with travel arrangements.
