Our 10-night Tuscany cycling tour is like our 8-night tour, but even better. Follow a similar itinerary to that of our shorter tour, but enjoy more rest and exploration days, including a day in Cortona. This extended trip will 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 Tuscany for yourself with our 10-night riding tour! See full itinerary below. Or click here to all of our other Tuscany bike tour offerings.
- 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: 11 days, 10 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$4,445
- Single Occupancy: US$4,995 (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$325
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
Our guide will meet you 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 – 59km
A glorious 70km ride of traffic-free 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 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. In Montepulciano, you will stay in a beautifully restored farmhouse that is owned by a family of wine exporters and experts. They are available to coordinate special tours and tastings, and even to host a class on how to cook an authentic Tuscan meal! We recommend dinner here both nights. The cooking school is not included in the price – so let us know in advance if you want this arranged. If you opt out, you are on your own for dinner, and there are many fine restaurants in the area.
Day 8: Montepulciano Exploration
You can walk to Montepulciano or cycle there and spend the day exploring this gem. It is your day to discover and enjoy. Dinner is on your own, including the possibility of taking the class at your hotel!
Day 9: Montepulciano to Cortona via Castiglione del Lago – 53km
Head into Umbria today, to Lake Trasimeno, where you will stay in the lovely village of Castiglione del Lago. The 53km ride from Montepulciano to Castiglione del Lago is easy and quick, which allows more time in either your start or finish town. 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.
Day 10: Cortona Exploration and Monte Petrano
What you do today is up to you—hit the road on your bike or explore the town. There are some beautiful rides in the area (the 2009 Giro had a mountaintop finish at Monte Petrano, which is not too far from Cortona). However, a day in town might be spent exploring the narrow steep streets and enjoying the medieval architecture. Dinner is on your own tonight. We will pick up your rental bikes later in the day.
Day 11: Cortona Departure
Depart for your next destination from the local train depot. We can help you coordinate your departure.
