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Featured Hotel: Castello di Casole

Here, you’re royalty. Welcome to the Timbers Resort ranked the #1 Resort in Europe by Travel + Leisure magazine, Castello di Casole.

A beautifully restored castle dating back to the 10th century and set on a stunning 4,200-acre private estate, Castello di Casole is a guest and guide favorite. This five-star boutique hotel boasts a destination spa, gourmet and relaxed dining, and exquisite suite accommodations that effortlessly combine the old world Tuscan charm of its storied past with modern luxuries of today.

Trek Travel Castillo di Casole Tuscany Cycling Vacations

The Restoration

Castillo di Casole and its surrounding villas were restored using traditional methods and reclaimed materials found throughout the estate, preserving its rich history.

Maintaining the Land

In the 1800’s the estate played host to over 30 farms rich in wheat, olives, grapes and livestock. Now, you can vacation among 100 acres of organic vineyards and olive groves.


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Serenity Now

Rejuvenate after a day in the saddle at the Essere Spa. This space was formerly the estate’s wine cellar, and its barrel-vaulted ceilings and expansive views of the valley are a sight to behold. Choose from a full treatment menu inspired by local ingredients and featuring a collection of Etruscan, traditional and modern therapies. Or unwind at your own pace in one of the many pools or steam rooms.

A Culinary Oasis

Whether you dine at the cozy Pazzia, the ever inviting Bar Visconti or the unforgettable Tosca, you can expect rustic dishes in the Italian tradition infused with a bit of the unexpected. Handmade pasta, fresh organic vegetables and local fish and game are paired with wines from the best wineries in Italy to bring to life recipes that will “stir the soul”.


Trek Travel Castillo di Casole Tuscany Cycling Vacations


Indulge your senses in the rolling hills of Tuscany

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If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date?
Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

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).

Level 2:

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 (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

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).

Level 4:

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).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

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