Tuscany
Idyllic riding through the Italian countryside
Ride from village to village on an immersive Italian cycling adventure.
If your idea of a Tuscan bike vacation evokes visions of rolling golden hills, mid-ride espresso stops, climbs to medieval hilltop villages, wood-fired pizza, and a nightly glass of Chianti, and you’re spot on for what you’ll experience during this cycling camp. We’ve curated our favorite routes, ranging from 40-70 miles, to showcase a variety of areas in the Tuscan countryside, with options to go fast, slow, long, or short. Don’t worry; there will be plenty of downtime to enjoy this spectacular region. Wine tasting, a cooking class, soaking in a natural hot spring, and touring Siena are all on the itinerary.
Highlights
- Bike among vineyards and olive groves on daily guided and supported rides
- Enjoy family-prepared meals by our Italian hosts, including pizza made in a wood-fired oven
- Stay in cozy bed-and-breakfast accommodations off the beaten path
- Explore Siena, taste wine and try the local cuisine
- Take part in an authentic Italian cooking class
Food
It doesn’t get more authentic than this: Our food in Tuscany is prepared fresh by the Italian family who runs Palazzo a Merse, the bed and breakfast where we stay. Many of the meats are sourced from a farm down the road, and the veggies are grown in the field behind the property or by the neighbors across the street. Meats are cooked over an open flame, and pizzas are prepared in a 500-year-old wood-fired oven. Family B&B meals are balanced with dining out to enjoy the local cuisine.
Accommodations
Meet your new extended family at Palazzo a Merse, a restored 18th-century farmhouse where we’ll spend the week. Owned by our guide Andréa Rossi and his wife and sister’s family, the rustic Tuscan B&B is about 10 kilometers from Siena in the quiet countryside of Val di Merse. Relax in the spacious, shady garden, or enjoy breakfast or a glass of wine as you lounge around the outdoor pool. Family-style meals are cooked by our hosts and served outside when weather allows.
ITINERARIES
Tuscany Road - 6 Nights
Benvenuti in Toscana - Arrival Day
Guests will arrive in Italy, and our staff will do Florence Airport (FLR) pickups. After you register, we will email a list of suggested hotels for guests planning to arrive early. If arriving early we ask that you meet back at the Florence airport, it’s easy to take the train to/from downtown Florence. Please email us your arrival/departure plans, including flight numbers.
Everyone will have time to settle into the B&B and enjoy our first chef-prepared meal.
After lunch, our mechanics will work on building guest bikes or fitting people to their rentals. We will depart for an afternoon shakeout spin once all the bikes are ready, and all the guests have arrived.
Today’s Ride: Arrival Spin
20-25 miles & 1,000′ – 1,500′
Chiusdino
This beautiful loop will take us around the Val de Merse area of Tuscany, with options to shorten or lengthen the route. We’ll stop at a café in Chiusdino and see the Abbey of San Galgano, a 13th century gothic style church.
In the afternoon, we’ll taste wine at Trecciano one of our favorite wineries in Tuscany.
Today’s Ride: Chiusdino
40-48 miles & 3,000 – 4,100′
Il Molinello Agriturismo
This ride point-to-point tour takes us through the beautiful Tuscan countryside from our B&B to a small agriturismo property near Asciano – Il Molinello. The route sweeps through the heart of the Val D’orcia region with quintessential views of Tuscany. Here we will have lunch, tour their lavender farm, and check out their L’Eroica museum.
Looking for more miles? We have an option to ride back home post-lunch on a different route.
Today’s Ride: Il Molinello AgriturismoÂ
32-56 miles & 2,700 – 4,800′
Pievescola Loop
Today, there are two options: a recovery tour around the B&B or a 3-hour ride to Pievescola with a café break in the village.
After the ride and lunch, we’ll visit Siena. We’ve organized an optional walking tour, which is a great way to learn about the area’s amazing history. Dinner will be enjoyed in the heart of Siena.
Today’s Ride: Pievescola Loop or Recovery Ride
20-40 miles & 1,300 – 3,200′
Discover Chianti
Learn more about the legend of that famous black rooster as we take a tour of the Chianti region. We’ll shuttle to the start, and mid-ride, we’ll enjoy a coffee stop in the village of Gaiole, where the Eroica Gran Fondo starts and finishes. The route finishes in the medieval village of San Gusme, where we’ll enjoy lunch.
After lunch, we’ll return to the B&B, where the family will host a cooking class. You’ll learn how to make homemade pasta and tiramisu (among other dishes), so when you host your next dinner party, you can show off your new skills!
Today’s Ride: Discover Chianti
32-36 miles & 3,200 – 3,800′
Val d’Orcia
The day starts with a van shuttle from the B&B to Grotti in the heart of Tuscany. The ride finishes in the small village of San Giovanni d’Asso, and we cap it off with a beautiful lunch overlooking the Tuscan countryside.
Today’s Ride: Val D’orcia
37 miles & 3,500′
Ciao - Departure Day
Shuttles will run to the Florence airport all morning, with the last shuttle leaving at 11 a.m. Please email us your departure times.
Today’s Plan: Departure Day
Checkout by 11 a.m.
DATES & PRICES
- 2025
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May 18 - 23 Road at Il Molinello B&B - 6 Day$3,875 / Person Many Spots Available
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May 24 - 30 Road - 7 Day$4,560 / Person Almost Full!
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Sep 13 - 19 Road - 7 Day$4,560 / Person Fully Booked - Join Waitlist
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Sep 29 - Oct 5 Road - 7 Day (JW Private Trip)$4,560 / Person Fully Booked - Join Waitlist
DETAILS
What's Included
- 7 days/6 nights accommodations (double occupancy)
- Airport transfers to/from Florence International Airport (FLR)
- All meals (breakfast, lunch, dinner)
- Wine tastings, walking tour, cooking class!
- Mechanical support (including bike build and breakdown)
- Professional trip guides
- Daily sag support
- Ride nutrition products
- High-quality ride photos
What's Not Included
- Airfare
- Bike rentals
- Gratuity for guides
- Mid-ride café stops
- Personal shopping
Optional Activities
- Wine tasting
- Tuscan cooking class
- Siena walking tour in the evening
- Visit to San Galgano Abbey
Questions?
BIKE OPTIONS
Rent A Bike
Traveling through the airport with a bike—and paying for it to fly—is not everyone’s idea of a fun way to start a vacation. Fortunately, we offer high-quality, full carbon bikes on all of our trips across the United States and Europe. Want to just show up and ride? Just bring your shoes, pedals, helmet, and saddle (if you want), and rent one of ours.
Bring Your Own
Your bike is yours—we get it. Bringing your own bike has obvious advantages in terms of individual comfort. Before your trip, we suggest getting a tune-up at your local bike shop so it’s ready to roll for your week of riding. Once you arrive, we’ll be sure to have our mechanics build it and help with any necessary tweaks. Check out some helpful resources here:
Skip The Bike
If you or your travel partner want to enjoy the trip and explore a new destination without a bike, drop us a line and we’ll discuss options. Some trips are better suited for non-rider participants than others.
TRIP TEAM
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