Italy

Tuscany Cycling Vacation

Idyllic riding through the Italian countryside
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  • From $3495
  • Location Tuscany, Italy
  • Duration 7 Days / 6 Nights
  • Rider Level 2 / 3 / 4 / 5

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, 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, short or not at all (one camp offers an itinerary for non-riding travel partners). Don’t worry, there’s also 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

  • Daily guided and supported rides among vineyards and olive groves 
  • Family-prepared meals by our Italian hosts, including pizza made in a wood-fired oven
  • Cozy bed-and-breakfast accommodations off the beaten path
  • Explore Siena, soak in a hot spring, taste wine and try the local cuisine
  • Take part in an authentic Italian cooking class
  • Non-riding itinerary for travel partners available upon request
Tuscany Cycling Trip - The Cycling House Italy
Tuscany Cycling Trip - The Cycling House Italy

Food

It doesn’t get more authentic than this: Our food in Tuscany is prepared fresh by the Italian family who runs 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 Palazzo a Merse 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.

Tuscany Cycling Trip - The Cycling House Italy

Accommodations

Meet your new extended family at Palazzo a Merse, a restored 18th-century farmhouse bed and breakfast where we’ll spend the week. Owned by our guide Andréa Rossi and his wife and sister’s family, the rustic Tuscan farmhouse 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.

ITINERARY

Riders will arrive at the Florence Airport or the Siena Train Station, and we will shuttle to B&B Palazzo a Merse.

Anyone who is renting a car can arrive at the B&B anytime after 11 a.m. We’ll head out for an arrival day spin (~2 hours) to explore our surroundings for the week.

Today’s ride:

Arrival day spin:
21 miles, 1,044 feet of climbing

We will ride around the Val de Merse area of Tuscany on this beautiful loop, with options to shorten or lengthen the route. We’ll stop at a café in Chiusdino and see the Abbey of San Galgano.

In the afternoon, we’ll go wine tasting at one of our favorite wineries in Tuscany.

Today’s ride:

Chiusdino: 39 miles, 2,976 feet of climbing

This ride is a point-to-point tour through beautiful Tuscan countryside from our B&B to a small agrotourismo property near Asciano, sweeping through the heart of the Val D’orcia region.

In the afternoon, we’ll head to Montalcino to see where Brunello wine is produced.

Today’s ride:

B&B Point-to-Point (Val D’Orcia): 36 miles, 3,287 feet of climbing

Option to extend the ride by pedaling up to Montalcino!

There are two options today: either 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 go visit Siena. We’ve organized an optional walking tour, which is a great way to learn about the amazing history in this area. Dinner will be enjoyed in the heart of Siena.

Today’s ride:

Recovery Loop: ~1 hour

Pievescola Loop: 40 miles, 3,334 feet of climbing

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, which is 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 shuttle back 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’ll be able to show off your new skills!

Today’s ride:

Chianti Tour: 37 miles, 3,447 feet of climbing

Option to add mileage on for those that want more riding.

We’ll shuttle to the start of our ride in d’Elsa. On a 41-mile route, we’ll ride to San Gimignano, a Unesco World Heritage Site, and take a café break.

Riders who want extra mileage can ride back home to the B&B.

Today’s ride:

San Gimignano: Main route is 41 miles, 3,410 feet of climbing

Longer route 60 miles, 4,70 feet of climbing

Checkout is 11 a.m. Riders will pack up, and we’ll shuttle back to the Florence Airport or the Siena Train Station for departures.

Today’s plan:

Shuttles to Siena and Florence

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Explore each day's ride details including distance, elevation and course profiles.

DATES & PRICES

DETAILS

What's Included

  • 7 days/6 nights accommodations (double occupancy)
  • Airport transfers to/from Florence International Airport (FLR)
  • All meals (breakfast, lunch, dinner) for 7 days
  • Wine tasting
  • Mechanical support (including bike build and breakdown)
  • Professional trip guides
  • Daily sag support
  • Ride nutrition products
  • High-quality ride photos
  • Question about COVID-19 and what we’re doing to keep our guides and guests healthy and safe? Contact us.

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 San Galgano Abbey

Questions?

Have more questions? View our FAQ page or call us at 406-312-5770.
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BIKE OPTIONS

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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.

Available this trip:
Focus Coyo
Manufacturer: Focus
Type: Road
Cost: $300 / trip
Italian E-Bike
Manufacturer: Univega
Type: E-Bike
Cost: $350 / trip
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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:

Shipping your bike

Flying with your bike.

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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

GUEST REVIEWS

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LEAVE A REVIEW
Phil R., Washington DC
September 17, 2019
Wonderful balance between seeing the sights and enjoying Tuscan culture and riding. The B&B was very comfortable. The garden is amazing, I enjoyed my R&R time there.
James R., Murfreesboro, TN
September 12, 2019
I have been on other cycling trips with other companies and this trip was the best-supported trip I have had. The Cycling House team was terrific and the Rossi and Parini families were a delight. The food was excellent and fortunately, the weather was spectacular. I did not find a shortcoming in the trip. I will readily recommend it to my cycling friends.
Show All Reviews
Phil R., Washington DC
September 17, 2019
Wonderful balance between seeing the sights and enjoying Tuscan culture and riding. The B&B was very comfortable. The garden is amazing, I enjoyed my R&R time there.
James R., Murfreesboro, TN
September 12, 2019
I have been on other cycling trips with other companies and this trip was the best-supported trip I have had. The Cycling House team was terrific and the Rossi and Parini families were a delight. The food was excellent and fortunately, the weather was spectacular. I did not find a shortcoming in the trip. I will readily recommend it to my cycling friends.
Scott S., Cherry Hill, NJ
June 25, 2019
The experience was amazing, from the rides, the food, the B&B, the guides, the bike rental. I enjoyed all of the stops in the cities and towns. I liked that there were excursions after the rides. The stories and history told were great also. I would recommend the trip as is to anyone!
Mike P., Missoula, MT
June 26, 2019
The Italian experience is so much more than the bike. TCH has done well collaborating with an amazing Italian family and their incredible surroundings. Riding through historic medieval villages while experiencing local Italian culture and history is something everybody should get to experience. We stayed in the beautiful countryside, in a stone mill built in 1200s. And a pool, with a view of lemon trees, palm fronds and birds buzzing overhead. And a beer fridge. Easy Living.
Les P., Jackson, WY
June 25, 2019
Great staff! Loved the family home cooked meals and the outdoor setting in the country. The guides did a nice job at managing the different paces of all the riders.