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Traveling To Cuba: Need To Know

So the allure of old, American-made cars, hand-rolled cigars, and back ally Cuban music streaming into the city streets has captured your sense of adventure. We couldn’t be more excited to announce our People-to-People tour to Cuba, one of the few cycling trips available that meets the US legal requirements. We are excited to explore this culturally rich nation with you during the experience of a lifetime.

Cuba is in a unique time in history, constantly changing as a growing American tourism market emerges. With regular flights departing U.S. soil bound for Cuba and regulations loosening, now is a great time to see and experience the charm of this developing country.

If you’re interested in visiting the island but unsure how it all works, below are some tips to get you started on researching your dream cycling vacation to Cuba.

Experience vintage Cuba on a Cuba bike tour

Is it legal to travel to Cuba? What does People-to-People mean?

Technically, traveling to Cuba for a leisurely beach vacation is still illegal for Americans. Your trip must fall under one of the 12 categories of permitted travel set forth by the Treasury Department’s Office of Foreign Assets Control (OFAC). One of these categories is educational activities, including People-to-People interaction. What does this mean exactly and how will affect your travel to Cuba? It means you can travel to Cuba if you, “Maintain a full-time schedule of educational exchange activities intended to enhance contact with the Cuban people…and that will result in meaningful interaction between the traveler and individuals in Cuba.” You won’t just pedal through Cuba. You’ll spend time with locals each day in a variety of settings, whether it is sharing experiences over coffee or a mojito, visiting a local sugar plantation, or meeting with artists and authors to hear their stories. We have taken care of designing a trip that meets the legal requirements so you can enjoy an authentic and worry-free vacation.

Please take note of the Planning for your Trip section on our Cuba trip page. There is a lot more information regarding travel requirements both before and after your trip. Traveling to Cuba presents unique challenges, and we want to ensure you have the best experience possible.

Experience vintage Cuba on a Cuba bike tour

Fun and Flexible

Because Cuban tourism is just begining to develop, traveling there presents unique challenges not found in more common destinations such as Western Europe. Hotel quality can vary significantly and plans may change at the last minute. Infrastructure in Cuba is not at the same level as our other destinations and resources can be limited. We have selected the best possible hotels, which are centrally located in historic towns, instead of isolated all-inclusive resorts offered by our competitors. These allow for a more enriching cultural experience, but it means that you may forgo some of the comforts and amenities that you are used having available on other Trek Travel vacations. We are leveraging years of trip design expertise and relationships with local partners to make your trip as smooth and comfortable as possible, but we suggest bringing your sense of adventure along for this journey. After all, this is Cuba!

At Trek Travel, our internal mantra is simple: fun and flexible. It means that no matter the circumstance, our rockstar guides will handle any curveball thrown their way while always keeping our guests’ experience and safety as their main priority. On this trip, we invite you to adopt our mantra, keep an open mind, and enjoy what authentic Cuba has to offer before it is gone.

Experience vintage Cuba on a Cuba bike tour

Why go with Trek Travel to Cuba?

On our People-to-People journey to Cuba, expect to have an incredible and authentic experience while engaging with locals at every turn. Our trip designers have worked hard with local partners to ensure you get a unique view into Cuban life. You will burn plenty of energy each day as we enjoy four days of cycling between some of Cuba’s oldest colonial towns, take a walking tour in each (including the grand finale tour of La Habana Vieja), lace up your hiking boots for a day hike in the mountains, and snorkel in the warm waters of the Caribbean. Combined with educational People-to-People experiences, your vacation to Cuba is an authentic itinerary you’ll remember for the rest of your life.

Allow us to take care of the logistical hassles of traveling to Cuba. Your safety and well-being is our primary concern. You will have the full resources of Trek Travel behind your trip, including our knowledgeable trip consultants who will help you prepare, two Trek Travel guides, two local guides, and a driver once you are there.

Our Cuba People-to-People itinerary is not for everyone. But for those seeking a true adventure to a burgeoning destination, it is sure to entice. The possibilities are endless for this country and its tourism infrastructure. But with that comes change, and now is the time to experience Cuba’s rich and engaging culture at its best. We hope you will join us.

Other great resources for planning your Cuba bike tour:

General travel information from our friends at Travel + Leisure.

Health information from the CDC.

Getting ready for Cuba from Cuba Explorer.


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