Tuscany Trail Villa-to-Villa Gravel Tour
Bike the iconic Strade Bianche gravel of the Tuscany Trail, with full support and luxury accommodations.
Over 6,000 cyclists from around the world flock to Tuscany to ride the famous Tuscany Trail, its private gravel roads accessible for just one precious week every year. This 450 km odyssey unfolds across rolling vineyards, medieval hill towns, and rugged shorelines. Otter takes this iconic, unsupported ride and elevates it to a truly extraordinary adventure.
From the moment you arrive, every detail is handled. We provide premium bikes and gear and expert mechanical support to ensure you ride with confidence and comfort each day. Your luggage is seamlessly transferred between stops, and support vehicles are always close by, providing you with hearty fare and ice cold drinks, and leaving you free to focus on the ride, the scenery, and the joy of the journey.
At day’s end, you’ll find yourself in a hand-picked boutique inn or private luxury villa, where rustic charm meets refined hospitality. Evenings unfold over long tables with Tuscan wine, farm-to-table feasts, and the joy of sharing stories from the day’s ride.
Additional activities add new dimensions: enjoy private wine tastings in Montalcino, a spa afternoon in Siena, sunrise yoga in the gardens of a centuries-old villa, guided strolls through UNESCO-listed towns like Siena and San Gimignano, or a guided culinary workshop in Florence before your journey begins.
This isn’t just the Tuscany Trail. It’s the Tuscany Trail reimagined: the challenge and beauty of Italy’s most famous bikepacking route, combined with effortless travel and Italian elegance. And this unforgettable trip becomes more meaningful, knowing your journey fuels Adventure Cycling’s mission to inspire, empower, and connect people to travel by bicycle.
DESTINATION
Tuscany, Italy
Tuscany in May feels like a painting brought to life - rolling hills lush with green, vineyards sprouting new growth, and fields awash with poppies and wildflowers. The weather is ideal for cycling, with mild mornings, warm afternoons, and long golden evenings. Riders will enjoy the beauty of the region’s famed strade bianche (white gravel roads), winding past olive groves, cypress-lined lanes, and medieval hill towns like Siena, San Gimignano, and Pienza. Off the bike, the pleasures are equally rich: savoring Brunello in Montalcino, wandering cobbled piazzas, or lingering over long Tuscan dinners under the stars. Spring in Tuscany blends the exhilaration of cycling with the timeless rhythm of Italian country life.
DETAILS
Dates
May 18 - 26, 2026
Primary Activity / Level (?)
Cycling / Level 4
Luxury
Pricing
$8,950 - double occupancy per person
$10,050 - single occupancy per person
A $750 refundable deposit secures your spot. Balance due 75 days before departure.
ACCOMMODATIONS
Throughout your journey, you will stay in luxury boutique inns and private villas, hand-picked to balance comfort and charm, and targeting locations that divide the ride route into comfortable segments. Beginning in Florence and continuing along the Tuscany Trail (TBD!), you will stay in some of Tuscany’s most iconic towns and countryside villas.
Highlights:
Luxury boutique inns and private villas with spacious social spaces plus quiet nooks for private downtime
All properties have ample indoor and outdoor spaces to enjoy and many have a pool, so you'll be rewarded with creature comforts in your time off the bike.
Ensuite bathrooms in every bedroom, stocked with premium bath products
Fast, reliable WiFi throughout the property
For solo travelers choosing double occupancy, privacy screens and sound machines are provided for added comfort.
The Farm Stand, Otter's signature self-serve table of coffee, refreshments, and snacks, is available at all hours throughout your stay and is replenished frequently with fruits, fresh pastries, and other satisfying treats.
INCLUDED IN YOUR TRIP
We believe your trip should feel effortless and free from distracting logistics and the hassle of constantly opening your wallet. That’s why we include more. With Otter, every detail is handled and every experience is designed so that your energy stays focused on adventure, connection, and relaxation.
Accommodations
Thoughtfully selected accommodations that embody the true character of the region
Luggage and bike transfers
Transportation
Airport transfers in a luxury SUV or van
A support vehicle that follows the day’s route, distributes refreshments, assists with mechanical issues, and offers lifts
Transportation to and from the route and any included activities
Ad hoc local transportation to explore your surroundings, subject to availability. If unavailable, we are always happy to help you arrange transportation.
Meals
We design all of our meals to cater to active athletes with discerning palettes. Food will be plentiful and there will be options to satisfy a wide range of tastes and dietary needs, such as vegan, vegetarian, gluten-free, dairy-free, and high protein options at every meal. We source food locally and seek organic ingredients where possible. Travelers will also have the opportunity to inform us of any needs or special requests before the trip.
Daily (8) hearty breakfasts with diverse offerings, but always including premium rich coffee or made-to-order espresso, fresh fruits, an egg dish, breakfast meats, pastries and baked goods, yogurt and homemade granola.
Daily (8) picnic lunches and snacks, served mid-ride and designed for efficient energy transfer, including ice cold water and sports drinks
Daily (8) après ride gatherings, including varied offerings of satisfying appetizers and signature cocktails, craft beers, and local wines
2 dinners at our favorite local restaurants
3 dinners prepared in-house
“The Farm Stand,” Otter's signature self-serve table of coffee, refreshments, and snacks, is available at all hours throughout your stay and is replenished frequently with fruits, fresh baked goods, chips, bars, and drinks.
Gear
Premium bicycles and bike accessories, optimized for the riding conditions and your preferences. For guests who choose to bring their own bike, Otter will receive (if shipped), assemble, and tune it prior to your arrival, and will dissemble and package it for its return home.
Daily bike handling, cleaning, tuning, and storage
A swag bag including an Otter jersey, local treats, and items to make your trip more enjoyable
GPS
Activities
Fully supported daily rides
Morning yoga
1 massage
A walking tour of Florence
Expert bilingual guides with extensive local knowledge
Note: Entry to the Tuscany Trail (approx. $100) is not included, as riders must sign up individually. You will receive instructions with your "Adventure Starts Here" packet, emailed after you book.
Sample Itinerary
May 18 – Arrival in Florence
Transfer from the Florence airport to a local private estate
Bike fittings and test rides
Time to explore the grounds, take a spin, and settle in
Evening welcome reception and dinner with your guides, introducing the adventure ahead and its logistics
May 19 – Florence Local "Warm Up" Ride
Hearty breakfast followed by a light ride out of Florence, leaving city streets for rolling vineyard hills
Mid-ride gourmet lunch, snacks, and ice cold drinks to reward and refuel
Afternoon walking tour of Florence’s Renaissance treasures or time to relax
Dinner spent exploring the local cuisine and culture on your own, with local recommendations
May 20 – Start the Tuscany Trail
Early breakfast and departure from Florence to arrive in Campiglia Marittima with plenty of time to pick up packets
Start of the Tuscany Trail!
**Until the final route is announced, we cannot be certain of the exact route, but the following is a good example of a typical day:
May 21 to 25 – A Day in the Life
Hearty breakfast and made-to-order espresso served on the patio
Ride challenging gravel climbs, sweeping descents, and gently rolling strade bianche averaging 75km per day with 3,500 feet of elevation gain. The SAG van will provide the ultimate flexibility, enabling riders to lengthen or shorten their rides as desired.
Pass through private estates and postcard-perfect towns each day, with options to stop at local eateries and town squares.
Stop for a mid-ride gourmet lunch, snacks, and ice cold drinks to reward and refuel.
Post-ride activities include massages, exploration of the local town, soaks in nearby thermal waters, pool time R&R, all while your bike is washed, tuned, and stored.
Dinner includes Tuscan wine, farm-to-table feasts served in the villa, or nights out in treasured local eateries
May 26 – Departure
Enjoy a leisurely farewell brunch on the patio.
Transfer to the Florence airport for onward flights.
Our Nonprofit Beneficiary
Adventure Cycling, a nonprofit that inspires, empowers, and connects people to travel by bicycle
The Mission:
"We believe that adventure, whether small or large, can be transformative. To live a life of discovery, we must unplug, break from our routines, feel the wind on our brows, and welcome opportunities to feel awe and wonder. A bike is simply the mechanism to get you there. Through inspiration, empowerment, and connection, we open the door to adventure for everyone."
TRIP FUNDRAISING ESTIMATE
$10,000+
Guests will receive a donation receipt documenting their tax deductible contribution within one week of the trip conclusion.
Frequently Asked Questions
We believe your trip should feel effortless and free from distracting logistics and the hassle of constantly opening your wallet. That’s why we include more. With Otter, every detail is handled and every experience is designed so that your energy stays focused on adventure, connection, and relaxation.
Accommodations
-
Thoughtfully selected accommodations that embody the true character of the region
-
Luggage and gear transfers, as needed
Transportation
-
Airport transfers in a luxury AWD SUV or Sprinter van
-
For bike tours, a support vehicle that follows the day’s route, distributes refreshments, assists with mechanical issues, and offers lifts
-
Transportation to and from daily activities
-
Ad hoc local transportation to explore your surroundings, subject to availability. If unavailable, we are always happy to help you arrange transportation.
Meals
We design all of our meals to cater to active athletes with discerning palettes. Food will be plentiful and there will be options to satisfy a wide range of tastes and dietary needs, such as vegan, vegetarian, gluten-free, dairy-free, and high protein options at every meal. We source food locally and seek organic ingredients where possible. Travelers will also have the opportunity to inform us of any needs or special requests before the trip.
-
Daily hearty breakfasts with diverse offerings, but always including premium rich coffee or made-to-order espresso, fresh fruits, an egg dish, breakfast meats, pastries and baked goods, yogurt and homemade granola.
-
Daily lunches (unless noted, as in ski days) and nutritious snacks
-
Après festivities, including varied offerings of satisfying appetizers and signature cocktails, craft beers, and local wines
-
Gourmet dinners at our favorite local restaurants, renowned culinary establishments, or prepared in-house at private estates (unless noted as free nights)
-
“The Farm Stand,” Otter's signature self-serve table of coffee, refreshments, and snacks, is available at all hours throughout your stay and is replenished frequently with fruits, fresh baked goods, chips, bars, and drinks.
Gear (activity dependent)
-
Premium bicycles and bike accessories, optimized for the riding conditions and your preferences. For guests who choose to bring their own bike, Otter will receive (if shipped), assemble, and tune it prior to your arrival.
-
Premium trekking/mountaineering gear
-
Complimentary Otter gear and a swag bag
-
Daily gear cleaning, maintenance, and storage of gear to ensure optimal performance
-
GPS for rides
Activities
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All activities as outlined in the trip itinerary, except those noted as “Additional Activities”
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Entrance fees to historic sites, museums, parks, and all other exclusive events
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Gratuities for baggage, porters, and service related to accommodations
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Expert bilingual guides with extensive local knowledge, where applicable
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Airfare (unless noted, as in Private Charter trips)
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Dinner on free night(s)
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Lunch when noted (as in ski days, to accommodate on-mountain flexibility)
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Spa services and other additional activities not specifically mentioned in “What’s Included.”
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Excursions and activities not outlined in the itinerary or referred to as “additional activities.”
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Gratuities for Otter guides
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Travel protection
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Ski gear (available on request)
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Ski lift tickets (since many guests will have passes)
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Otter partners with nonprofits to provide them with risk-free and effortless fundraising. We commit to guaranteeing 10% of the trip's proceeds will go to donations, with the possibility of additional funds raised through activities (such as trunk shows where the vendor donates a portion of the sales) and in-kind donations. There will be no active fundraising or "hard sells" on the trip, but you will receive more information about the nonprofit you are supporting, and guests will always have the option to donate more if moved to do so.
Guests will receive a donation receipt from the nonprofit within one week of the trip's conclusion, along with "total funds raised" for the trip.
A $750 per person no-risk deposit is required to confirm your reservation. This deposit is fully refundable until the final payment due date.
Final payment is due 75 days prior to departure. At that time, any unpaid balance will be charged, and the deposit becomes non-refundable. Reservations made within 75 days of departure require full payment at the time of booking.
Guests will receive an email reminder of the upcoming payment one week before it is processed, and will have the opportunity to change the payment method on file.
Up to 75 days before departure: Your deposit and any payments made are fully refundable.
45–74 days before departure: You will receive a 50% refund of the total trip cost.
15–44 days before departure: You may apply 50% of the total trip cost as a credit toward any future Otter & Co. trip, valid for 12 months from the date of cancellation.
Within 14 days of departure: All payments are non-refundable.Certainly. It's important to share the fun with friends and loved ones, even for those not interested in the primary activity. On most trips, such as ski trips, non-participating partners will have endless options to fill their days. On others, such as point-to-point cycling tours, they may need to be comfortable with some van rides (and time by the pool). If you'd like to hear more about what a "day in the life" would be like for a non-participating guest on a specific trip, please reach out and we can get into more detail about the logistics and the experience.
Absolutely. We're happy to accommodate and offer e-bikes for all trips, unless specifically noted. Batteries will be charged each night and spares will be carried in the support vehicle to ensure you always have power.