Mix sun-drenched landscapes with equal parts history, rustic charm, the warmth of the Toscani, the region’s incredible cuisine and wine and you have the recipe for an unforgettable and magical cycling vacation. This week-long luxury trip accommodates any level of cyclist in classic Trek Travel style, with full van support, great bikes and unforgettable experiences. Pedal country roads through lush vineyards, dine on fresh local fare and enjoy the allegria that permeates Tuscany! Each day, you can ride, relax, and explore: taste the Brunello wines of Montalcino, perfect your "cucina italiana" at a private cooking class, or enjoy the hospitality of the Mascheroni Stianti family at the villa on their estate in Volpaia.
Trip Wow’s
Enjoy the hospitality of the Mascheroni Stianti family at an exceptional gourmet lunch and wine tasting in the Villa of their estate at Castello di Volpaia.
Feast on a delicious meal prepared by a local chef and our friend, Roberto In a small village garden in the Chianti region.
Take part in an exclusive, private cooking class at a local winery and olive oil farm where you’ll create your own Tuscan feast under the guidance of an Italian master of the kitchen.
Days 1 – 2 | San Quirico d’Orcia Stay at Palazzo del Capitano Sample famous regional wines–Brunello di Montalcino and Vino Nobile di Montepulciano | Cycle the stunning Val d'Orcia | Soak your feet in the therapeutic Roman springs, Bagno Vignoni
Day 3 | Casabianca Stay at Borgo Casabianca Ride through the dramatic landscape of the Crete Senesi | Explore the abbey of Monte Oliveto Maggiore | Relax in the country luxury of Borgo Casabianca.
Days 4 – 6 | Chianti Stay at Castello di Spaltenna Cycle the winding roads of the Chianti Classico region | Visit Radda in Chianti, the capital of the Ancient League of Chianti | Create a culinary masterpiece at cooking school | Enjoy a visit to the cellar of Volpaia’s fortress and an exclusive wine tasting and lunch with Carlo and Giovannella, the proprietors
Palazzo del Capitano | San Quirico d’Orcia, Italy A historic palazzo in the heart of charming San Quirico, Palazzo del Capitano boasts newly renovated rooms, an indulgent spa, and tranquil gardens. Its mix of modern luxury and rich history will enchant you.
Borgo Casabianca | Asciano, Italy Set deep in the hills of Tuscany, this collection of 18th century buildings was once a farming complex and is now elegantly restored into a refined and luxurious hotel, far from the bustle of modern life. Stroll the bucolic grounds and enjoy spectacular views of the surrounding countryside from the pool!
Castello di Spaltenna | Gaiole in Chianti, Italy This medieval hamlet, complete with castle and church, is now an elegant hotel surrounded by vineyards and woods. The hotel weaves modern luxuries with its rich history, offering uniquely decorated rooms, a full wine cellar, and both outdoor and indoor pools.
What’s Included in the Trip Price
5 nights of accommodation
Daily breakfast, 4 lunches, 2 social hours, 4 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? Fall in Tuscany is usually clear and sunny, with warm daytime temperatures (75F-90F) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your vacation.
What are the daily rides like?
Rider Type | 3
Average Daily Mileage | 35
Terrain | hilly
Average Daily Elevation | 2,500
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. Tuscany is best suited for our Type 3 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 3 miles 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:
Discover Pienza, a UNESCO World Heritage Site.
Explore the ancient walled towns of Montalcino, and discover the wines that made it famous
Therapeutic springs and spa in Bagno Vignoni
Discover why Tuscan wines are so renowned during our private wine-tasting
Opt to visit historic Siena
Indulge at the 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)
Tuscany 2013
May 26-31, 2013
Guaranteed Date*
$3,999 per person | $950 single occ.
Jun 9-14, 2013
Guaranteed Date*
$3,999 per person | $950 single occ.
Sep 15-20, 2013
Guaranteed Date*
$4,299 per person | $950 single occ.
Sep 22-27, 2013
Guaranteed Date*
$4,299 per person | $950 single occ.
Sep 29-Oct 4, 2013
Guaranteed Date*
$4,299 per person | $950 single occ.
Oct 6-11, 2013
Guaranteed Date*
$4,299 per person | $950 single occ.
Tuscany 2014
May 11-16, 2014
$3,999 per person | $950 single occ.
May 25-30, 2014
$3,999 per person | $950 single occ.
Jun 8-13, 2014
$3,999 per person | $950 single occ.
Sep 21-26, 2014
$4,299 per person | $950 single occ.
Sep 28-Oct 3, 2014
$4,299 per person | $950 single occ.
Oct 5-10, 2014
$4,299 per person | $950 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.
When we asked our guests what their favorite WOW's were from their Tuscany bike vacations, here is what they said…
We just wanted you to know that we thoroughly enjoyed our trip through Tuscany this fall. All of the hotels, restaurants, and activities were beyond our expectations. We are very appreciative!—Dan & Mariah
While walking toward the cloister that had the famous frescoes of St. Benedict at Monte Oliveto Maggiore, in a lower courtyard, I saw an elderly man of small stature, struggling with a ladder; I had no idea how he was going to lift it up against a wall. I opened a gate and offered assistance. He didn’t speak much English and I sure don’t speak either Latin or Italian. Using the international pointing language, we succeeded in trimming an overgrown vine and picking up the debris. When we finished, he pointed at himself and said ’Father’ and I pointed at myself and said ’Presbyterian’. He smiled and I left to have lunch with the Trek group. I never mentioned the experience except to my wife, but it was definitely a highlight of the trip. The week was one of the highlights of my life. Riding up the hills of Tuscany continually reminded me how lucky and blessed I am.—John
Great place in the world. Very interesting hotels. Wine tasting was a nice touch.—Tony
I loved the fellow riders on this trip. They were so much fun. Tuscany was amazing.—Sue
Tuscany and its people. The riding was great and the scenery magnificent. The people were friendly and the joyful culture was heartwarming.—Jim
I always say mortals don’t get to go on these kinds of trips. It was amazing in all aspects. We will travel with you again and again.—Janice
Palazzo del Capitano
Borgo Casabianca 
Castello di Spaltenna
