Discover the magic of cycling in Tuscany, where rolling vineyards, medieval hilltop towns, and world-class cuisine come together for an unforgettable journey. This Tuscany self-guided bike tour is designed for travelers who want to enjoy a relaxed pace, taking in the stunning landscapes, savoring authentic Tuscan food and wine, and soaking in the region’s rich history—all from the saddle of a comfortable bike.
This 4-night cycling tour follows quiet country roads through some of Tuscany’s most scenic villages, offering breathtaking views, delicious local wines, and charming boutique accommodations. Whether you’re a seasoned cyclist or a leisure rider looking for a taste of adventure, this is the perfect way to explore the heart of Tuscany by bike.
Tour Highlights
- Cycle Through Tuscany’s Iconic Landscapes – Ride along peaceful, rolling countryside surrounded by vineyards, olive groves, and historic villages.
- Explore Medieval Towns & Villages – Visit enchanting Tuscan gems like San Gimignano, Volterra, and Radda in Chianti, each with its own unique charm and history.
- Savor Tuscany’s Best Food & Wine – Enjoy authentic Tuscan cuisine, from fresh pasta and truffle dishes to Chianti Classico wine tastings in local vineyards.
- Stay in Charming Accommodations – Rest each night in handpicked boutique hotels and countryside villas that showcase the beauty and hospitality of Tuscany.
- Flexible Self-Guided Itinerary – Ride at your own pace with detailed route maps, expert local support, and options to shorten or extend your daily rides.
Who Is This Tour For?
- Cyclists Who Love Stunning Scenery – If you dream of riding through rolling vineyards and sun-drenched olive groves, this Tuscany bike tour is for you.
- Food & Wine Enthusiasts – Enjoy leisurely stops at family-run wineries, sip world-renowned Chianti Classico, and savor farm-to-table Tuscan specialties.
- 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.
- Leisure & Recreational Cyclists – This Tuscany self-guided bike tour is designed for those who enjoy cycling but prefer a relaxed, moderate pace with plenty of time for sightseeing and exploring.
- Travelers Seeking an Authentic Tuscan Experience – Immerse yourself in the region’s history, culture, and breathtaking landscapes, away from the crowds.
See full itinerary below. To learn more about all of our Tuscany bike tour offerings 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: 5 days, 4 nights
Service: Supported, Private, “Self Guided” tour. GPS Guidance! But your first day is FULLY GUIDED! 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: Siena
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 |
| Greve in Chianti | Albergo del Chianti |  |
| Radda In Chianti | Relais Vignale |  |
| Siena | Hotel Athena |  |
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.
- 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$2,145
- Single Occupancy: US$2,595 (for single room occupancy on multiple person tours)
- Solo Tour: Please contact us
Bike Rental Per Person:
- Road Bike: US$290
- eBike: US$290
- Hybrid: US$220
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/21mi
Your Tuscan adventure begins in Florence, the Renaissance capital, where you’ll meet your guide in the morning. After a proper bike fitting, your guide will accompany you out of the city, navigating the lively streets and leading you into the heart of Chianti’s picturesque landscapes.
Once outside Florence, the ride becomes a tranquil journey through vineyards and olive groves, leading to Greve in Chianti, the gateway to Chianti Classico wine country. Upon arrival, check into your charming hotel, relax, and explore the historic town square, artisan shops, and local enotecas. Your luggage will be waiting for you at the hotel, so feel free to unwind with a glass of Chianti wine before enjoying an included traditional Tuscan dinner.
Day 2: Greve in Chianti to Radda – 30km/19mi
Today’s ride takes you deeper into Chianti’s wine country, following scenic country roads lined with cypress trees and vineyards. Along the way, stop in Castellina in Chianti, a delightful medieval town filled with wine cellars, charming cafés, and historic stone streets.
For those who want a longer ride, an optional 20km extension is available, offering extra time in the saddle while soaking in stunning panoramic views. Arriving in Radda in Chianti, check into your elegant countryside hotel, then take a leisurely stroll through this charming hilltop village. Tonight, enjoy another included dinner featuring the best of Tuscan cuisine.
Day 3: Radda Loop Ride – 29km/18mi
Today is all about exploring the best of Chianti on a scenic loop ride through the region’s most picturesque spots. Visit Badia a Coltibuono, a stunning former abbey-turned-winery, and pedal through Gaiole in Chianti, a charming town known for its wine festivals and medieval architecture.
For those who want a little extra adventure, an extended ride will take you to Castello di Meleto, a historic Tuscan castle with breathtaking views and an optional wine tasting experience.
After a day of cycling and sightseeing, return to Radda and enjoy an evening at your own pace. Tonight’s dinner is on your own—take the opportunity to discover a local trattoria or enoteca, where you can indulge in fresh handmade pasta, wild boar ragu, or a perfectly grilled bistecca alla Fiorentina.
Day 4: Radda in Chianti to Siena – 33km
Your final ride is a breathtaking 33km journey along quiet, rolling backroads leading to Siena, one of Tuscany’s most iconic and beautiful medieval cities. Along the way, soak in the expansive views of vineyards, hilltop villages, and golden wheat fields, a postcard-perfect Tuscan landscape.
Upon arrival in Siena, check into your hotel located inside the historic town gates, placing you right in the heart of the action. Spend the afternoon exploring the stunning Piazza del Campo, visiting the magnificent Siena Cathedral, and getting lost in the city’s winding medieval streets.
Tonight, dinner is on your own, giving you the chance to experience Siena’s renowned culinary scene. Find a cozy restaurant serving pici pasta with truffle sauce, wild boar stew, or a glass of Brunello di Montalcino while taking in the city’s magical evening ambiance.
Day 5: Siena Departure
After a leisurely breakfast, it’s time to say goodbye to Tuscany’s rolling hills and charming villages. We’ll help coordinate your train transfer back to Florence or your next destination. Whether you’re continuing your Italian adventure or heading home, you’ll leave with incredible memories of cycling through Tuscany’s most breathtaking landscapes.
