Get off the grid and onto a gravel biking adventure through the heart of Tuscany. This Tuscany gravel bike tour offers an exhilarating journey along the strade bianche, Tuscany’s iconic white gravel roads that host legendary Italian pro races and the famous Eroica event. Ride through the striking landscapes of the Crete Senesi, known for its stunning, otherworldly views, and continue to the scenic Val d’Orcia, a UNESCO World Heritage site. Explore quintessential Tuscan villages like Gaiole, the picturesque town of Montalcino, and the majestic city of Siena, celebrated for its history and charm. Savor the flavors of Tuscany with indulgent pasta dishes, handmade pizzas, and world-renowned wines such as Chianti and Brunello. Whether you’re a seasoned gravel cyclist or seeking a new adventure, this is the ultimate unpaved Tuscan cycling adventure you won’t want to miss.
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Discover the charming, medieval towns of Montalcino, San Quirico, and the historical center of Siena as well as the UNESCO World Heritage site, Val d'Orcia
Pedal on the same hilly paths as the historic and famous bike events the region is known for
Take part in a private wine tasting and taste superb Tuscan wines, including the world-recognized Brunello di Montalcino
Stay in a 16th-century transformed village that today is a luxury destination in the heart of the Tuscan countryside
Explore white gravel roads — the strade bianche — lined with cypress trees and immerse yourself in Italy’s less-traveled paths
Capanna Suites in the Tuscan countryside during sunset
Capanna Suites - Agriturismo, Spa, & Wine Club
Immerse yourself in the Tuscan countryside, not only by bike but also during your stay at a luxury farmhouse and spa, in the heart of Brunello wine region.
It is an incredible journey to discover the hidden corners of the Tuscan territory. Nothing is like the "white roads" of Tuscany; perfect for cycling, quiet, picturesque, rich in history, and ready to host cyclists, whether it's a pro race or an historical re-enactment. At the top of each new hill, I am rewarded with unique, postcard scenery. The atmosphere that you breathe is one of a kind, the people are cheerful and light-hearted and never refuse a good glass of Chianti or Brunello.
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Loving the exceptional and consistent TT experience. Top level guides, logistics, accommodations and equipment. Enjoy beautiful scenery, great rides, company, food and wine. Repeat. There is no better way to vacation!
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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.
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Great Ride
Ride on the Strade Bianche Pro race course and enjoy the views ranging from the lunar landscape of the Crete Senesi and fortified villages to endless green hills.
Book early for the best price
Guaranteed
Join Waitlist
Private
Limited Availability
Where to Arrive
Airport:
Florence Airport (FLR)
Pick-up location:
Piazza della Indipendenza, Florence, Italy
Pick-up time:
10:30 AM
Where to Depart
Airport:
Florence Airport (FLR)
Drop-off location:
Santa Maria Novella Train Station, Florence Italy
Drop-off time:
12:30 PM
Additional Arrival Information
We suggest that you arrive at least one day prior to the start of your Tuscany Gravel bike trip, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into the Florence Airport (FLR).The airport is about three miles (just under five kilometers) from the town center. You can take a taxi (approximately 20€) directly to the hotel, or a bus which departs hourly.
You can also fly into Rome or Milan and take a train or flight from either city. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. Trains depart twice hourly. Tickets can be purchased at a Biglietteria office or from ticket machines. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform. The ride takes 30 minutes. From Roma Termini, transfer to a train for Florence. The Eurostar trains depart frequently and are the quickest. The trip takes one and a half hours and costs between 44-62€ one way per person. In Florence, taxis are available to take you to your hotel. Taxi service is available from Rome Fiumicino Airport to central Rome for approximately 50€. For information about travel through Milan’s Malpensa Airport (MXP), consult the website www.airportmalpensa.com.
On the first day of your trip, your Trek Travel guide will meet you at 10:30 AM in the center of Piazza della Indipendenza in Florence, Italy. Look for the bus stops on the road that runs between the two statues in the square. Dolce Salto Café (R, Via Ventisette Aprile, 65, 50129 Firenze FI, Italy) is located just across the street. GPS coordinates for the meeting point: 43°46'47.9"N 11°15'15.2"E.
After meeting your guides, you'll take a 90-minute shuttle to your lunch destination for your first taste of Tuscan cuisine. Following lunch, your guides will conduct a bike fitting to ensure you're comfortable on your Trek Checkpoint SLR 7 for the week. Please keep your first day’s riding gear easily accessible, separate from your main luggage, to make the bike fitting and initial ride as smooth as possible.
If you will be late for the pick-up or are going to miss it altogether, please inform your guides. If you cannot reach them, call our first hotel, Villa Curina Resort in Castelnuovo Berardenga (+39 0577 355630) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel in Villa Curina Resort for approximately 150€. The trip takes over an hour from the center of Florence.
Additional Departure Information
You will say farewell to your guides at 11:00 AM at your final hotel, Capanna Suites in Montalcino. You’ll depart by private shuttle for the Florence train station, arriving at around 12:30 PM. Please, do not reserve a seat prior to 1:30 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. Train schedules, fares and bookings can be made on the Trenitalia website at www.TrenItalia.com, or www.thetrainline.com, for other European destinations.
Get your first taste of gravel in the famous wine region of Chianti
Overview
Your Trek Travel guides will meet you near the bus stop in the center of Piazza della Indipendenza in Florence, Italy, at 10:30 AM on the first day of the trip. This city is a marvel of Renaissance art and where you'll find the Uffizi galleries, the Duomo, and the Galleria dell'Accademia, home of Michaelangelo's David. From here you'll take a one-hour private shuttle to the charming town of Villa a Sesta. After a delicious Tuscan, picnic-style lunch, you'll be fit to your Trek Checkpoint gravel bike, and then we're off on a rolling, scenic ride through stunning cypress trees and to the impressive Abbadia a Monastero, a monastery dating back to the 9th century. We'll arrive at our hotel where you can relax, unpack, and prepare for our first night's dinner and social hour at the hotel.
Hotel
Villa Curina Resort
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
Villa a Sesta
Savor a Tuscan lunch with Chianti views before setting off on your first ride through the rolling hills of this idyllic region.
Ride Options
Ride Option1
TODAY'S RIDE:
Villa a Sesta to Villa Curina - Approximately 15 mi | 24 km and 1,049 ft | 322 m
Discover the history of vintage cycling in Gaiole
Overview
Buongiorno! We arise in Chianti with an appetite for a hearty breakfast and a menu of adventure. Today you will cover some of the most beautiful roads in the area. After a brief warmup on the pavement, you'll turn onto the gravel roads toward the historic, medieval towns of Vagliagli and Radda. In centuries past these limestone-white, unpaved roads, known by their Italian name strade bianche, were the only connections between those villages! We'll stop for lunch at a cafe of your choosing in Gaiole, a small Tuscan village with a unique history of vintage cycling. Don’t miss a visit to the La Bottega cycling store to learn more about the local cycling event with riders decked out in full vintage regalia, and pick up a souvenir to remind you of this special place. After lunch, we'll continue winding through fragrant vineyards to the cypress-lined entrance of Castello di Brolio, the famous castle that has been the home of the Ricasoli family for 800 years. The afternoon is yours for relaxing at the hotel followed by a delicious three-course dinner at your leisure.
Hotel
Villa Curina Resort
Meals included
Breakfast | Dinner
Highlight of the Day
Visit La Bottega
Visit La Bottega in Gaiole to soak up vintage Strade Bianche cycling culture, shop unique souvenirs, and feel part of Chianti’s heritage.
Ride Options
Ride Option1
TODAY'S RIDE:
Radda to Gaiole Loop - Approximately 40 mi | 64 km and 3,900 ft | 1,200 m
Ride Option2
SHORT OPTION:
Radda to Gaiole with Shuttle - Approximately 24 mi | 38 km and 2,560 ft | 780 m
Ride Option3
AVID OPTION:
Radda to Gaiole to Castelnuovo Loop - Approximately 46 mi | 74 km and 4,432 ft | 1,351 m
Explore epic views and vistas of Tuscany and enjoy coffee in Siena
Overview
It's another spectacular day of cycling discovery and adventure as you follow the white gravel routes featured in one of Italy’s most famous pro races, taking you to beautiful Siena, the start and finish point to the race. In this picturesque town you can enjoy the views while sipping your macchiato in the vibrant Piazza del Campo, Siena’s main historic square and local meeting point. From Siena, you'll head south through the almost lunar landscape of Crete Senesi to Buonconvento, where we'll stop for a special lunch with incredible, sweeping views of Tuscan rolling hills. With 360 degree vistas, you can appreciate the contrast between the dense vineyards of Chianti and the vast, rolling fields of Val d'Orcia. We arrive this afternoon at our destination, an elegant luxury agriturismo, that has a unique perspective on the traditions of this beautiful region. Tonight, your guides will shuttle you to the nearby walled fortress of Montalcino where we will enjoy a guided walking tour followed by a dinner of your choice.
Hotel
Capanna Suites
Meals included
Breakfast | Lunch
Highlight of the Day
Piazza del Campo
Ride through narrow streets of Siena to Piazza del Campo, the start and finish point of the Strade Bianche pro race.
Ride Options
Ride Option1
TODAY'S RIDE:
Villa Curina to Buonconvento with Shuttle - Approximately 30 mi | 50 km and 2,620 ft | 800 m
Ride Option2
AVID OPTION:
Villa Curina to Siena to Capanna - Approximately 37 mi | 60 km and 3,200 ft | 1,000 m
Pedal through Val d'Orcia and enjoy farm-to-table dining
Overview
Rise today with a cappuccino in preparation for some of the region's most stunning views. Our ride today takes us to the hills of Val d'Orcia. The Val d'Orcia is an incredible agricultural landscape that is a UNESCO World Heritage site due to its continued adherence to Renaissance layout and aesthetic. It is like cycling inside a painting! You'll continue through the medieval village of San Quirico d’Orcia, with buildings dating to the 15th century and epic views from every hilltop. Don't forget to stop and savor the scenery and maybe even take a few pictures before we head back to the hotel. We'll gather this evening for a private wine tasting and immerse ourselves in the captivating world of superb Tuscan wines. Tonight, we celebrate a week's worth of memories with a special dinner prepared with seasonal ingredients sourced straight from the hotel farm and perfectly paired with select local vintages. We'll toast together and recap the highlights of an incredible week!
Hotel
Capanna Suites
Meals included
Breakfast | Lunch | Social Hour | Dinner
Highlight of the Day
Featured Meal | Il Passaggio Restaurant
Enjoy an inviting atmosphere at Capanna Suites, where the chef’s seasonal farm-to-table menu and fine wines create an unforgettable evening.
Ride Options
Ride Option1
TODAY'S RIDE:
Pienza to Lucignano D'Asso Loop - Approximately 38 mi | 61 km and 3,900 ft | 1,190 m
Ride Option2
SHORT OPTION:
Pienza to Lucignano D'Asso with Shuttle - Approximately 25 mi | 40 km and 2,600 ft | 790 m
Ride Option3
AVID OPTION:
Capanna to Lucignano D'Asso Loop - Approximately 44 mi | 70 km and 4,270 ft | 1,300 m
Farewell spin through the vineyards
Overview
It's sadly time to say farewell to this Signature Tuscan unpaved adventure. Choose to rise early for one last glorious spin at the base of Montalcino through lush, fragrant vineyards as a warm sun rises over the Tuscan countryside. Or, skip the ride and savour a cappuccino at the hotel, recounting the memories of a week well-spent. However you say goodbye to the sumptuous heart of Italy, you'll be sure to take a small bit of it in your soul as you leave.
Hotel
Capanna Suites
Meals included
Breakfast
Ride Options
Ride Option1
TODAY'S RIDE:
Brunello Loop - Approximately 9 mi | 14 km and 780 ft | 240 m
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. Some non-riding options on our Tuscany Gravel bike tour are:
Looking for a break from traffic and the usual routes? Our gravel rides are the perfect escape! While the amount of pavement varies from destination to destination, you can count on minimal traffic once you hit the dirt. And since you'll be off the beaten path, you may encounter fewer services - that's where our guides come in handy. They'll make sure you have everything you need, whether it's a flat tire fix or a local recommendation for the best post-ride treat. And with support from our team available on and off the bike, you'll have everything you need for a smooth and enjoyable ride - even through some of the bumps on the trail.
Set in the Chianti countryside near Siena, Villa Curina Resort occupies a restored 16th-century hamlet surrounded by rolling hills and gardens. Rooms are comfortable and traditional, the on-site restaurant focuses on regional Tuscan cooking, and outdoor spaces offer open views across the landscape—especially at sunset. The atmosphere is relaxed and authentic, with a strong sense of place rather than formality.
Capanna Suites is a boutique agriturismo in Montalcino that blends rustic chic design with modern luxury and comforts. Rooted in the local terroir, it offers Brunello wines, farm-to-table dining, and optional spa treatments—all in a setting that’s both charming and relaxing.
New in 2026! The Checkpoint SL 7 AXS Gen 3 is a carbon gravel bike built for epic rides. Its lightweight frame features Gravel Endurance geometry with IsoSpeed comfort tech, while 45 mm tires smooth out rough terrain. With a wireless SRAM Force XPLR AXS drivetrain featuring a wide 10–46T 13-speed 1X gearing, and powerful disc brakes—everything you need to go wherever the gravel leads.
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New in 2026! Trek’s Checkpoint+ SL6 AXS is a lightweight e-assist bike built for miles of fun. The TQ HPR60 electric-assist motor adds a quiet boost up to 15 or 28 mph (region specific), making climbs and long days easier. Carbon wheels and frame, plus IsoSpeed technology, keep it quick and responsive. Gravel riders will use 45 mm tubeless, knobby tires, while Classic riders will be on 38mm road tires—showcasing the bikes versatility. With SRAM’s 12-speed AXS wireless shifting and disc brakes, every move is in your control.
Upgrade to the Checkpoint+ SL 6 AXS for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. See specific trip dates for available bike options.
Trek Travel Guides
From the moment you meet our guides, you'll understand the difference. You'll feel the genuine care they take to make your vacation perfect. From their expert support to sharing their favorite hidden spots, they tailor every moment to you.
Certified Guides
Know Before You Go!
We want you to be fully prepared for your cycling vacation of a lifetime. This involves making sure that you choose the appropriate trip for you and that every aspect of your experience is flawless. Each Trek Travel trip is unique to ensure maximum enjoyment every time.
Your Trip Need to Knows:
Florence, Italy
Florence is the timeless heart of Renaissance art and culture. Spend a few days wandering beneath Brunelleschi’s iconic dome, strolling along the Arno, and visiting landmarks like the Duomo, Ponte Vecchio, and the Uffizi Gallery. Don’t miss Michelangelo’s David at the Galleria dell’Accademia, and if time allows, take in the views from Piazzale Michelangelo or visit the grand Piazza della Signoria. Museum hours vary, so pre-booking tickets is a smart way to skip the lines and make the most of your time. We recommend the following accommodations for your pre-trip stay:
Where to Stay
Hotel Rapallo
Hotel Rapallo is a charming boutique hotel nestled in the heart of Florence. Recently renovated, it offers 26 thoughtfully designed rooms that blend contemporary comfort with classic Italian warmth. Select accommodations feature private terraces, providing guests with a serene space to enjoy the city's ambiance. www.hotelrapallofirenze.it
Palazzo Castri 1874
Blending traditional charm with contemporary elegance, this hotel offers a seamless fusion of classic and modern design. Guests can enjoy magnificent views of the Cathedral of Santa Maria del Fiore, relax amidst the fragrant lemon and magnolia trees in the exclusive inner garden, and rejuvenate at the state-of-the-art spa. These elements combine to create an unforgettable escape from everyday life. www.palazzocastri.com
Hotel Orto De' Medici
Hotel Orto de' Medici offers a unique blend of modern comfort and Renaissance history in the heart of Florence. Set within the very garden where a young Michelangelo first honed his sculpting skills in 1489, the hotel provides guests with a serene retreat amidst blooming white roses and timeless elegance. www.ortodeimedici.it
Rome, Italy
Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:
Where to Stay
Hotel Barocco
This 37-room hotel is tucked away in central Piazza Barberini. It boasts a refined, simple style with all of the comforts and amenities needed for a relaxing Roman getaway. www.hotelbarocco.com
Hotel Capo d’Africa
Located in the heart of Imperial Rome, between the Forum and the Domus Aurea, the Hotel Capo d’Africa boasts contemporary decor within a beautiful, early 19th-century building. www.hotelcapodafrica.com
Mecenate Palace
In front of the Basilica of Santa Maria Maggiore, this hotel is within walking distance of most of the important monuments and shopping areas found in Rome. Guests can enjoy a panoramic view of the city from the hotel’s roof garden. www.mecenatepalace.com
Spring and fall in Tuscany are usually clear and sunny, with pleasant daytime temperatures (70-85ºF/21-29ºC) and evening temperatures 10-15 degrees cooler. A jacket will be useful in the evening. Rain is always a possibility, however, so be prepared with wet-weather gear and warmers in order to best enjoy your cycling vacation.
View our Packing List
To reserve your space on a trip, you can either call us at 866-464-8735 to speak with an expert Trip Consultant or book online any time by clicking the “BOOK THIS TRIP” icon near the upper right of each destination’s overview page.* Once you have submitted your reservation online, a Trip Consultant will contact you within one business day to answer any questions you may have and to confirm space, bike, and room availability on your desired trip. Your booking will be finalized once your no-risk deposit is paid. If you make a reservation more than 90 days prior to the trip, a $750 no risk deposit is due at the time of booking.** If you reserve your trip less than 90 days prior to the departure, the full balance is due at the time of booking. Once your booking is complete you will receive an email confirmation with important information pertaining to your trip.
*Please note that select trips cannot be booked online at this time. For those trips, please call a trip consultant at 866-464-8735.
**Deposit amounts vary for all Race, Cross Country, Special Edition, Ride Camp, and Self-Guided tours. Please confirm deposit amounts for all trips with your Trip Consultant at time of booking.
When a trip is booked, a guest confirmation email is immediately sent out. One week prior to the trip start, you’ll receive an email containing your trip start meeting location reminder and any last-minute information that you’ll need to know. You will also receive instructions to download the Ride with GPS app before your trip to provide you the day to day plan and daily route guides.
Our trips are guaranteed to run once we have one confirmed booking on the trip.
Click here to view our full guaranteed policy.
Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangements for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Select trips are not guaranteed.
We understand things happen in life and sometimes you have to cancel or change your tour.
Read our Cancellation Policy
Our Trip Consultants are available to assist and can answer your questions. Please call us at 866-464-8735.
Trek Travel recommends that you purchase a travel protection plan to help safeguard you and your travel investment against the unexpected. We offer a travel protection plan through Arch RoamRight that provides coverage for unforeseen events that could affect your ability to travel with us. Learn more about our Travel Protection
We've collaborated with a specialized travel agency committed to delivering tailored vacation planning, ensuring your entire Trek Travel journey is nothing short of unforgettable. Learn more about our Travel Services
Sharing the joy that comes with wow moments
Trek Travel guides are dedicated to making moments that last a lifetime, and we invite you to thank them with a trip gratuity. These are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this Gravel trip, we recommend between $200-$250 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience.
Like everything else about your vacation, the Trek Travel team is here to make this experience easier for you. While local currency is preferred, you may also tip through the following options:
Via PayPal (please have this account set up in advance when possible) or with your guest services representative on the phone before or after the trip.
Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.
You cannot put a price on a wow. But you can show your thanks for an exceptional experience.
Didn't find what you were looking for? Check out our General FAQs section. You will find answers to the most common questions that don't necessarily pertain to a specific trip. See Gravel FAQs
Want to learn more about our trips? Watch our recorded Guide-Led Virtual Events—just visit our Trek Travel Youtube Channel and search for your trip.
Log in to see upcoming trips, preferences, and much more.
Sign up to personalize your experience and trips.
Our trips are guaranteed to run once we have one confirmed booking on the trip. Click here to view our full guarantee policy.
Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangements for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Select trips are not guaranteed.
This trip is currently sold out, but you may be added to the waitlist in the case of availability.
If a date is marked with Limited Availability, there are few spots left to book. We will secure additional rooms from our hotels before confirming your reservation.
Looking to travel with a small group? Ask our trip consultants about private trips and learn more.
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
Trek Travel offers three hotel levels to match your style. Luxury hotels provide elegant, thoughtful touches with exceptional hospitality. Explorer hotels blend modern amenities with local charm in unique settings. Comfort hotels are casual and conveniently located near Trek Travel activities.
Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).
Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).
Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).
Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).
Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (600 m).
Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).
Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).
Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).
Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).
Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).
Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).
Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).
Explore beautiful destinations with a curated blend of guided activities, local cuisine, handpicked accommodations, and itineraries to suit every traveler, from laid-back adventures to luxurious escapes.
Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
See the pros in action at the biggest cycling events of the year.
Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.
Train like the pros in some of their favorite riding destinations.
Enjoy a bike tour on your schedule with just your chosen travel companions.
Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself
