Relaxed Tuscany Bicycle Tour - 7 Night

Our 7-night relaxed Tuscany bicycle tour is similar to our 4-night relaxed tour but even better.  Follow a similar itinerary to that of our shorter tour, but extend the riding to San Gimignano and Volterra.  You also have days to relax and explore Siena and San Gimignano.  This extended trip will still find you riding some of the most scenic roads in the world, sipping cappuccinos in the mornings, sampling fine Chianti wines in the afternoon, and savoring sumptuous regional foods by night.  The lauded natural beauty and romantic scenes of Tuscany have not been overstated.  What better combination for a romantic getaway or family vacation?  Come and discover Italy for yourself with our 7 night Tuscany bicycle tour!

We love customizations, and if you would like to modify the below itinerary please ask us.

See full itinerary below. Also, to learn more details about our Tuscany bike tours CLICK HERE.

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.

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
Greve in Chianti Albergo del Chianti Albergo del Chianti Greve
Radda In Chianti Relais Vignale Relais Vignale Radda
Siena Hotel Athena  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.

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$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
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 Greve in Chianti – 32km
Our guide will meet you in the morning near the heart of Florence. After being fitted properly to you 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 30km to ride into Chianti, to Greve. After checking into 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 village and try the local Chianti before dinner.  Dinner is included tonight.

Day 2: Greve in Chianti to Radda – 30km
Your second day in Tuscany centers around a ride along small, pedaling back roads to Radda in Chianti.  Along the way, you can visit the beautiful village Castellina. Add on an additional 20km if you want a bit more time in the saddle.  Dinner is included tonight.

Day 3:  Radda in Chianti to Siena – 33km
A glorious 33km ride of quiet backcountry roads is in store for you today, with your journey culminating in Siena.  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 4:  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.  If you would like a loop ride around Siena, work with your guide to create an appropriate route. Dinner is again on your own tonight so keep your eyes peeled for the best option.

Day 5:  Siena to San Gimignano – 41km
Exit Siena the way you came in, with grand views of the city.  You head northeast through Colle d’Elsa which is known for its beautiful crystal glassware.  You will understand why San Gimignano is called the “city of towers” as you approach your destination.  Our hotel is next to the towers near the center of town. Dinner is included this evening.

Day 6:  San Gimignano Exploration
Today is another day off the bike, and take in the beautiful hilltop town.  If you would like a loop ride around San Gimignano, work with your guide to create an appropriate route. Dinner is again at the hotel.

Day 7: San Gimignano to Volterra – 32km
You head farther east into lush forested hills of Pisa, and onto Volterra. Arguably Tuscany’s most beautiful hill towns, you will feel connected with the history of Tuscany and Pisa. Relax at the end of your ride or visit Volterra’s Etruscan gate and Roman theater.  At the end of today’s ride, we will we will retrieve your rental bikes. Dinner is on your own tonight.

Day 8:  Volterra Departure
Depart for Florence or elsewhere by taking the frequent buses that go to local train stations! We can help you with figuring out your transportation options.

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