The Heart of Tuscany - 8 Night

Go deeper into the heart of Italy with one of our longer Tuscany bicycle tours.  Immerse yourself in Italy’s rich culture while discovering the region on some of the most scenic rides in the world.  Sip cappuccino in the morning, sample fine Chianti in the afternoon, and savor sumptuous regional foods by night.  The lauded natural beauty and romantic scenes of Tuscany have not been overstated. Come and discover Tuscany for yourself with our 8-night bicycle vacation! See full itinerary below. Or click here to learn more about our other Tuscany bike tour offerings.


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.

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.

We generally target 3 and 4-star hotels, which we hand select to maximize comfort while minimizing cost. The star rating is using a French rating system, which has proven to be the standard around the world. Therefore we use the same standards in France and beyond.

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  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.

Tuscany Road Bike


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.

Tuscany Hybrid Bike






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.

Tuscany eBike





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).



  • 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.
Included in your tour fee is the use of one of our Garmin Edge Touring GPS units for the duration of your tour. These easy to use GPS units provide an excellent worry-free routing method that you can depend on throughout your tour. When you arrive the daily routes will be pre-loaded, and ready for you to use each day of your tour. All you have to do is start the daily route at the beginning of your riding day, and follow the highlighted line!

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.

garmin edge touring screens

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
What’s Next? Registering for your tour!

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 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
Our guide will meet you in the morning in the heart of Florence. After being fitted properly to your rental bike, you will hit the road with your local guide!  Your guide will ride with you, navigating the busy Florence streets and into Chianti giving you a fully guided experience highlighting the sites along your route. Once you leave the city, enjoy a lovely 49km to ride into Chianti, to Panzano. After checking in to your hotel, you will have time to relax, refresh yourself, and explore the town.  Your luggage will be there when you arrive, so feel free to enjoy the pool and try the local Chianti before dinner.  Dinner is included tonight.

Day 2: Panzano to San Gimignano – 41km
Your second day in Tuscany centers around a ride along small, rolling back roads to San Gimignano, the city of towers.  Add on an additional 20km if you want a bit more time in the saddle.  Dinner is included tonight.

Day 3:  San Gimignano Rest Day or Volterra Loop – 60km
You can take a day off of the bike to rest, shop, and explore San Gimignano, or instead ride the beautiful 60km loop to Volterra. One of the many famous hilltop towns of Tuscany, Volterra is full of fine shops and features a museum. Dinner is on your own tonight.

Day 4:  San Gimignano to Siena – 61km
A glorious 61km ride of traffic-free backcountry roads is in store for you today, with your journey culminating in Siena.  You have a 41km shorter option. A beautiful, small city, Siena is at the heart of the region.  Dinner is on your own tonight, so enjoy exploring the old city in search of all the culinary delights Siena can offer.  Our hotel is inside the town gates and perfectly situated for easy exploration of Siena and the surrounding areas.

Day 5:  Siena Exploration
Today is a day off the bike, one designed to allow you to fully explore the historic sites and do some gift shopping.  Dinner is again on your own tonight so keep your eyes peeled for the best option.

Day 6:  Siena to Montalcino – 53km
Exit Siena on small back roads with grand views of the city.  Head South on 53km of rolling roads to another small, historic hilltop town—Montalcino, the home of the famous Brunello wines.  You are on your own for dinner, and there are many fine options to select from.

Day 7:  Montalcino to Montepulciano – 40km
You depart Montalcino to start an eventful day.  The direct route is to Montepulciano is only 40km, but several options (some with hills) give you a chance to add as much mileage as you would like. Included along your ride is a stop in the town of Pienza, a great place for lunch and exploration.  For dinner, you are on your own.

Day 8:  Montepulciano to Cortona – 53km
Head into Umbria today, to Lake Trasimeno, where you will visit in the lovely village of Castiglione del Lago. The ride from Montepulciano to Castiglione del Lago is mostly downhill! Castiglione del Lago is perched on a promontory, overlooking the lake, and an excellent lunch stop.  Cortona is another gem.  Our favorite hotel is in the heart of the town to allow easy exploration on your last day.  Dinner is on your own tonight.  Explore this wonderful village in search of an ideal dinner spot.  Ask about Il Falconiere – it has a Michelin Star and is in the hills above town. We pick up your rental bikes later in the day.

Day 9:  Cortona Departure
Depart for your next destination from the local train depot. We can help you coordinate your departure.

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