Heart of Tuscany Bicycle Tour - 4 Night

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European Self-Guided Tours

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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 dinner. Dinner is on your own this evening. The village offers plenty of options.

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 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.

Location: Panzano in Chianti

Hotel: Villa Le Barone

Location: San Gimignano

Hotel: Hotel Relais Santa Chiara

Location: Siena

Hotel: Hotel Athena

Road Bikes

Full Carbon Road Bikes

Sizes: 50, 53, 55, 58, 61

Mixture of Shimano components with a compact double crankset.

Hybrid Bikes

Hybrid

Sizes: XS, S, M, L, and XL

Mixture of Shimano road and mountain components with a triple crankset.

eBikes

eBike

Sizes: S, M, L

Mixture of eBike components and Shimano Altus.

WHAT IS INCLUDED:

All hotel accommodations – mostly 3 and 4 star but ask for custom accommodation requests.
An OBT cycling jersey!
Detailed route notes, maps, and tourist information. This includes standard cue sheet, and RideWithGPS routes to upload to your own GPS device or use the RideWithGPS app.
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.

We work with only local guides, cooperating with those that have a love for cycling, and a desire to show guests the beauty of the land they call home. On our self guided tours we do not bring in guides from other destination to work with you. Having the local perspective only enhances your experience, providing insider knowledge and opportunities that only a local resident can offer. 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.

Tour Cost Per Person:

Double Occupancy

US$2,145.00

Single Occupancy

US$2,695.00 (from single room occupancy on multiple person tours)

Solo Tour

Bike Rental Per Person:

Road Bike

US$290.00

eBike

US$290.00

Hybrid

US$154.00

What’s Next? Registering for your tour!

Questions: First, please feel free to ask us any questions about the tour. Click the “Contact Us With Questions” button above. We are happy to help clarify any details.

Registration: Once you are ready to register, please click on the “Book Now” above and complete the registration form. EACH tour participant will need to be included in the registration. At the end of the registration for you will be asked for a US$1,000 deposit. Once we have all registrations, we will secure all of the details of your tour – hotels, bikes, etc.

Final Payment: All payments are due 60 days prior to your 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 more! For more information on our Terms & Conditions, please CLICK HERE.

We rely on RideWithGPS for all our route planning—it’s simply the best tool we’ve found. You can choose from three easy options: use the RideWithGPS app on your phone, sync the routes we provide with your GPS device, or download cue sheets for a classic navigation experience.

With your OBT tour you will be provided with a library of routes to be used throughout your day to day rides. Some days may have multiple ride options!

No matter your preference, we’ve got your GPS routing covered during your tour!

Experience the best of cycling in Tuscany on this 4-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 Siena, 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, and Siena.
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.