| Months |
September | View Dates» |
| Price (USD) |
From $3,499 | See Pricing» |
| Start & End |
Florence, Italy | Grosseto, Italy |
| Trip Length |
6 days | 5 nights |
| Rider Type |
3-4 | Learn More» |
| Daily Rides |
Options from 20 - 68 miles |
| Beyond Biking |
Historical Site Visit, Cultural Tour, Wine Tasting, Beach, Shopping |
| Trip Options |
Make it Private or Choose Your Own Date |
 |
Surrender to the magic of Tuscany as you cycle along quiet roads bordered by rolling hills, lush with vineyards and olive groves. We stay in the heart of Chianti, its wine renowned for centuries, so perfectly matched to the simple yet diverse and rich cuisine: creamy pecorino, truffles, decadent pasta and wild boar. Explore the medieval hilltop village of Radda in Chianti and discover the breathtaking city of Siena. Marvel at the landscape of the almost surreal Crete Senesi on your way to the coast. This alluring region, complete with charming locals, Tuscan sun and the Mediterranean will capture your heart. Chianti will truly provide you with the biking vacation of a lifetime.
Trip Wow’s
- Ride along challenging mountaintop roads lined with cypress trees in the beautiful Tuscan landscape.
- Savor Italian cuisine and discover local specialties like creamy pecorino, white truffles and wild boar.
- Discover the tradition of Chianti Classico.
- Wonder in amazement at the Piazzo del Campo in the immaculately preserved city of Siena.
- Meet the locals and learn how to live "la dolce vita!"
Days 1 & 2 | Chianti
Stay at Palazzo Leopoldo
Cycle through the rolling hills of the Chianti countryside | Discover exclusive Chiantis during our private wine tasting |Stay in Radda, the charming capital of the ancient League of Chianti
Day 3 | Siena
Stay at Borgo Pretale
Discover Italy's best preserved medieval city - Siena - with a private walking tour | Challenge yourself on rides to hilltop towns
Days 4 – 6 | Massa Marittima
Stay at La Cianella
Enjoy the small winding roads to the Tuscan coast and alongside the Mediterranean | Explore the wildly beautiful Maremma, home to Etruscan ruins and sparkling beaches
Palazzo Leopoldo | Radda in Chianti, Italy
Dating back to the 13th century and set in the historical center of Radda in Chianti, Trip Advisor award winner, Palazzo Leopoldo is an elegant villa with its own wine shop and spa. The hotel’s design melds ancient architectural details and contemporary comforts for an unparallelled stay. Enjoy the views of the surrounding Chianti hills from their specacular terrace with a glass of Prosecco in hand.
Borgo Pretale | Sovicille, Italy
Nestled in the tranquil forests of central Tuscany, this 13th century home has been restored into a beautiful hotel. The main tower and its surrounding buildings all share gorgeous views and the estate has a swimming pool, tennis court and walking paths for you to enjoy. Soak in the history of this ancient space that provides all the modern amenities you could want.
La Cianella | Massa Maritima, Italy
La Cianella takes its name from the 19th century fountain on property, "Fontana delle Cianelle". Surrounded by olive trees, La Cianella is set high on a hill with fantastic views of surrounding valleys. Intimate and inviting, the 19th century main structure now houses 12 charming, comfortable rooms. The outdoor swimming pool and tennis courts each offer unrivaled views of the surrounding countryside.
What’s Included in the Trip Price
- 5 nights of accommodation
- Daily breakfast, 3 lunches, 2 social hours, 3 dinners, and all snacks and drinks for each day
- The knowledge, support, and camaraderie of experienced guides
- Daily route support
- The use of a Trek Domane 5.9 carbon road bike, or Trek Domane 5.9 Women’s Specific Design carbon road bike (limited selection), or Trek 7.6 FX hybrid bike
- The use of Trek bike helmets and other gear and equipment to make your ride comfortable
- Trek Travel water bottles
- Private tours
- Entrance fees to all group events/activities
- All luggage transfers
- All transportation during the trip, including private coaches
- Comprehensive trip literature and complimentary Trek merchandise
- All gratuities for special events, local guides, transfers, hotels, and restaurants
- $300 Discount on a 5 or 6 series Trek Domane or Madone, or Project One purchased at your local Trek retailer
Not Included
- Airfare to and from the trip
- Transportation to the trip pick-up location
- Lodging before and after the trip
- Gratuities for Trek Travel guides
- Personal items purchased during the trip
- Some meals are not included in each destination, which allows you the opportunity to explore regional cuisine on your own. Your guides are happy to make recommendations should you so desire.
What is the weather going to be like?
The fall brings pleasant daytime temperatures (70F-80F) and evening temperatures 10-15 degrees cooler. Tuscany’s northern location means that it can be hit with the odd cold spell or rain shower. Light layers and a waterproof shell are recommended.
What are the daily rides like?
| Rider Type | 3-4 |
Average Daily Mileage | 39 |
| Terrain | hilly |
Average Daily Elevation | 2,100 |
On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Chianti to the Coast is best suited for our Type 3-4 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer. The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of 5km long. See Itinerary for specific daily ride distance and elevation options.
What are the options for a non-rider travel companion?
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. See Included In The Trip Price for more information.
Some non-riding options on this trip are:
- Explore the walled city of Siena
- Shop and explore the medieval villages of Radda, Lecchi, Monteriggioni and Casole D’Elsa
- Discover why Tuscan wines and olive oils are so renowned during our private wine-tasting
- Opt to spend a half day at a local spa
General FAQs
Didn’t find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don’t necessarily pertain to a specific trip.
| Trip | Dates | Price (USD) |
Chianti to the Coast 2013
|
Sep 1-6, 2013 |
Guaranteed Date* |
$3,499 per person | $1,100 single occ. |
|
Sep 8-13, 2013 |
Guaranteed Date* |
$3,499 per person | $1,100 single occ. |
| Chianti to the Coast 2014 |
Sep 7-12, 2014 |
|
$3,499 per person | $1,100 single occ. |
|
Sep 14-19, 2014 |
|
$3,499 per person | $1,100 single occ. |
Want to travel with your with friends, family, or colleagues? We can make any trip private. More»
Our dates don't fit your schedule? Use Travel Match and suggest your own date. More»
*Our 2013 trips are guaranteed to run once we have one confirmed booking on the trip. Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangments for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Guaranteed trips do not include Cross Country, Santa Barbara to Taos, Pyrenees Sea to Sea, or any Race trips.
Wow’s From Our Guests & More Photos
When we asked our guests what their favorite WOW's were from their Tuscany bike vacations, here is what they said…
Reward yourself with a velvety glass of Chianti, the fellowship of a few good friends, and a Tuscan meal so delectable you’ll wish you never had to leave. This trip is truly the vacation of a lifetime. –Meagan
