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People-to-People Multisport Adventure

Step into the heart of Cuba and immerse yourself in an authentic Cuban experience. Join us as we pedal between colonial towns and historic sites to uncover this fascinating destination. We'll visit Trinidad, Cienfuegos, the Bay of Pigs, Havana and more. Along the way, you can't help but soak up the culture as you take in the sights and sounds that each day has to offer. Before you leave, you can be sure that you will salsa in the streets, sip a few mojitos, try a Cuban cigar, learn about life in Cuba from the locals, and share lots of laughs and stories while you are at it.

Our People-to-People trip meets the legal requirements for Americans who travel to Cuba. Please read the More Information section thoroughly for important details on traveling to Cuba.
Prices Coming Soon
8 Days & 7 Nights
Rider Type: ?
2 - Recreational Non-riders Welcome
Hotel Style: ?
Bikes Included:
Prices Coming Soon View All Details
Trip Wows
Tour the plazas of Old Havana and cruise the Malecón in a famed classic car
Pedal through the lush green Valley of the Sugar Mills and visit the ruins of a sugar plantation
Snorkel above the coral in the glittering waters of the Bay of Pigs
Visit the vibrant colonial towns of Trinidad and Cienfuegos and learn to salsa with the locals
Watch the Experience
Touring Cuba by bike is the best way to tap into this fascinating country. You can’t help but encounter various Cubans as you roll slowly from town to town, and this trip is all about stopping to hear their stories. Each day brings a change of scenery and a new city to explore, ending with the crown jewel of Havana. It’s a rolling history lesson infused with rum, cigars, art, music, architecture and so much more. One thing is for sure, your perspective on Cuba will be forever changed by the experience. I hope you enjoy it as much as I did!
-Amy Davison, Trip Designer

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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There are currently no dates available to book for this trip or it is by request only. Please contact a Trip Consultant for more information on available dates.
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 Departure Dates:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*

2021 Departure Dates:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Welcome to undiscovered Cuba! This country is a clash of cultures, time periods, passions and sights. Your guides will meet you at the airport and once everyone has gathered, we will set off on a tour of Santa Clara. You’ll notice the homages to Che Guevara, the famed revolutionary, in artwork, installations and more. We’ll visit Che’s monument and learn about the final battle of the revolution that took place here. We’ll also visit a colonial theater, Teatro Caridad, before getting checked into our hotel for the evening. If you are arriving on the later flight, one of your guides will meet you at the airport and you’ll join the group for dinner. Tonight, your guides will fill you in on the plan for the rest of the week over social hour and dinner.

City: Santa Clara

Hotel America or Granjita

Included Meals:

Social Hour | Dinner

This morning after breakfast, we will gather by the bikes for a bike fitting session before we set off on our first ride. From Santa Clara, we pedal to Remedios, often referred to as the quieter, less touristy version of Trinidad. Once we arrival, we’ll enjoy a hearty lunch. This afternoon, we'll hire the local bicycle taxis to take us on a tour of their favorite parts of town, then we'll share stories with the drivers over a drink at a local cafe and learn more about their lives and livelihood. This evening, we'll celebrate with a welcome toast, dine at one of our favorite local paladars, and your guides will fill you in on what to expect during the rest of this action-packed trip.

Today's Ride:

Santa Clara to Remedios
Approximately 30 miles with 800 feet of climbing

City: Remedios

Hotel Real, Barcelona or Mascotte

Included Meals:

Breakfast | Lunch | Dinner

This morning begins with a shuttle to Yaguajay, about 45 minutes away, where we will get back in the saddle. We'll pedal our way south past verdant farmland and stop to visit with some of the locals—and refuel with some tropical fruit and cold guarapo—along the way. We'll break for a picnic lunch just before reaching Cabaiguan, and afterwards, you can choose to keep riding to the hotel or hop on the bus for the rest of the journey to Sancti Spiritus. If you love Caribbean history, you might think you've died and gone to heaven, as the town of Sancti Spiritus is over 500 years old, with beautiful villas, spirited softball games in the streets, and literal boatloads of culture. As we explore town, we will visit with local shop owners and learn about “La Libreta” or the ration card every Cuban family uses for weekly food supplies. On our way to dinner, we'll stop at the Taverna Yayabo for a drink while admiring Peunta Yayabo, a quadruple-arched bridge that was built by the Spanish in 1815 and is a National Monument. Enjoy dinner in a local paladar, then those with energy can head out for some evening music.

Today's Ride:

Yaguajay to Cabaiguan
Approximately 30 miles with 1,600 feet of climbing

Avid Option:

Yaguajay to Sancti Spiritus
Approximately 43 miles with 1,900 feet of climbing

City: Sancti Spiritus

Hotel del Rijo or The Plaza

Included Meals:

Breakfast | Lunch | Dinner

Today we begin with a short shuttle before we take to our bikes once again to pedal our way through the Valle de los Ingenios, the lush green valley that was the center of Cuba’s sugar industry. Tour the ruins of an old sugar plantation and climb the 7-story Iznaga Tower for a stunning view of the valley. We'll then make our way to Trindad, a vibrant city-museum which was designated a UNESCO World Heritage site in 1998. We will walk along Trinidad's cobbled streets before meeting local author, Julio Munoz, and learning about his beloved city firsthand. You'll have a chance to ask him about the Cuban economy, private enterprise and the political scene. Enjoy dinner at another local paladar. Trinidad is a power house for music, so those seeking more Cuban beat will find several options here.

Today's Ride:

Banao to Trinidad
Approximately 40 miles with 1,200 feet of climbing

City: Trinidad

Iberostar Grand Hotel or Las Cuevas

Included Meals:

Breakfast | Lunch | Dinner

Today starts with a 45 minute drive up into the Sierra del Escambray range for a little adventure amidst the tropical flora and fauna. We will hike to Caburni Falls, which drop some 200 feet to the Caburni River below. Revel in sweeping views of traditional farms and coffee plantations against a backdrop of cliffs and, of course, these almost undiscovered waterfalls. You'll have a chance for a refreshing soak in the medicinal waters mid-hike. Then after hiking up and out of the canyon, we'll visit a coffee farm and talk with the farmer about their trade. Afterwards, we'll board the bus for a 90 minute transfer—a good opportunity for a nap—to the seaside city of Cienfuegos, known as the Pearl of the South. It's been called the Paris of Cuba, with a strong backbone of art, culture, and a spirit that's vibrant enough to be French, yet passionate enough to be decidedly Cuban. Every neighborhood has a certain panache that's both timeworn and feisty. On arrival, if time permits and they are in town, we will hear a performance by the Cantores de Cienfuegos, a choral group that performs around the world. After a lovely dinner by the sea, if you are up for more, take a stroll along the Malecón.

City: Cienfuegos

Hotel La Union or Hotel Jagua

Included Meals:

Breakfast | Lunch | Dinner

Today begins with a short shuttle and then we take a downhill cruise to the sea and Playa Giron, which sits at the mouth of the Bay of Pigs. This historic landmark is a significant symbol in the story of the Cold War as the site of a failed military invasion of Cuba by a CIA-sponsored paramilitary group in 1961. We'll have an opportunity for to visit the Bay of Pigs Museum and then enjoy a picnic lunch. The Bay is a prime spot for snorkeling, so we'll take an hour or two to explore the coral and mystical sea caves teeming with tropical fish. We'll learn about the Caribbean ecosystem and why Cuba has the healthiest reefs in all the region. Afterwards, we'll depart for a three hour transfer to Cuba's cultural crown jewel, Havana. It's both the capital and commercial center of the country, but it's also a window into world history. Spanish colonial architecture is part of the city's DNA. The National Capitol Building is an iconic 1920s landmark, and La Habana Vieja, or "Old Havana" is home to the baroque Catedral de San Cristóbal and Plaza Vieja, both of which are a shining example of the architectural passion that the city is known for. We will check into the luxurious Gran Hotel Manzana Kempinski in the heard of Old Havana and reconvene for dinner nearby at La Calesa Real. After dinner, stroll Obispo Street where several bars and restaurants have live music.

Today's Ride:

Yaguaramas to Playa Girón
Up to 30 miles with approximately 350 feet of climbing

Today's Activity:

Snorkeling in the Bay of Pigs

City: Havana

Gran Hotel Manzana Kempinski

Included Meals:

Breakfast | Lunch | Dinner

Today is 100% dedicated to discovering Havana. We'll visit a cigar factory, and learn why Cuban cigars are such a rare and decadent treat for the true collector. We'll visit all four of Old Havana's famous plazas during a walking tour, ending with lunch in Plaza Catedral. Afterwards, it is on to Fusterlandia, the home of Cuban artist Jose Fuster ("the Picasso of the Caribbean"), whose artistic mission is to transform his community through a kingdom of mosaic creations. And finally, we'll be sure to take a ride in those classic cars before we gather for one last round of mojitos and a special farewell dinner at La Chansonier.

City: Havana

Gran Hotel Manzana Kempinski

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

What a rare opportunity this has been! Today we say our goodbyes over a final cup of Cuban coffee before you depart for your next port of call.

Included Meals:



What's Included

For us, the details matter most

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Trek FX S 4 Hybrid

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  • 7 nights of accommodation at the best available hotels
  • One experienced Trek Travel guide and one local Cuban guide to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support vehicle
  • Daily breakfast, 6 lunches and 7 dinners
  • Social hour on your first and last night of the trip
  • Ride a Trek FX Hybrid
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized photobook of your trip
  • Entrance fees for all activities, private tours and events



    Gratuities for your guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. USD or local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
    • Garmins are not provided on this trip due to local laws. Do not bring your own Garmin or other stand alone GPS device or it may be confiscated
    • Route Guides are not provided (the ride will be led by the guides and the group will stay together)
    • Airfare and transportation to and from the trip pick-up/drop-off locations
    • Lodging before and after the trip
    • Personal items purchased during the trip
    • Optional activities not scheduled by Trek Travel
    • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

    More Information

    Rider Level: 2 - Recreational?

    35 miles
    130 miles
    875 feet
    3,950 feet
    Please note that the number of paved roads to choose from in Cuba are limited and this trip contains more shuttling than our normal trips in order to get from destination to destination in a timely manner. The terrain is generally flat with a few mellow hills sprinkled in for good measure. The roads we ride are paved, and pavement is generally smooth but there will be some patches that are less well maintained. Cuba is best suited for our Type 2 Riders. Our Trek Travel guides can also easily accommodate Type 1 Riders, who seek less mileage or fewer uphills, with a boost in the van.
    Given the travel restrictions in Cuba and the fact that we change hotels daily (except for the final night), non-riders should be prepared to ride in the support vehicle during the day and take part in each day's people-to-people and other non-riding activities with the group. Please contact one of our Trip Consultants for more information. Some of the non-riding activities on this trip are:
    • People-to-People Exchanges
    • Hike in Topes de Collantes National Park
    • Snorkeling in Bay of Pigs
    • Swim in the Caribbean and natural pools
    • Bay of Pigs Museum
    • Walking Tour of Old Havana
    • Tour of Cigar Factory
    • Visit to Coffee Farm
    • Visit Manaca Iznaga Sugar Plantation
    • Classic Car Ride in Havana
    • Visit Fusterlandia
    • Musical Performance in Cienfuegos
    • Meet with Author Julio Munoz

    See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

    Averages and totals are calculated from our "Today’s Ride" options.

    Travel Details

    How to Get There

    Santa Clara Airport (SNU)
    12:00 PM or 5:00 PM
    Santa Clara Airport (SNU)

    Say Farewell

    Havana Jose Marti International Airport (HAV)
    9:00 AM
    Your Havana Hotel


    We suggest that you fly into Santa Clara Airport (SNU) on the first day of this trip. You will need to book a flight on JetBlue (from Fort Lauderdale arriving at 12:00 pm) or American Airlines (from Miami arriving at 5:00 pm) as these are the only two flights from the USA to Santa Clara on Saturdays. Depending on your home airport and connections, you may need to overnight in Fort Lauderdale or Miami the night before the trip. Please contact a Trip Consultant if you need assistance with flights.

    Don't forget to bring cash and exchange it for local currency (CUC Cuban Convertible Peso) at the airport. American credit cards will not work in Cuba.

    One of your guides will meet you at the Santa Clara airport at 12:00 PM (JetBlue) or 5:00 PM (American) depending on the flight you choose.

    If you miss your flight or it is delayed, please inform your guides as soon as possible. You will receive an email a week before the trip start with contact details for your guides.

    View our pre hotel recommendations


    We will offer a shuttle from your Havana hotel at 9:00 AM on the final day of the trip to the Havana Jose Marti International Airport (HAV). The shuttle takes approximately 40 minutes, and we recommend you do not book a flight before 11:45 AM. If you need to leave earlier or later, you may take a taxi to the airport. Cabs are plentiful and cost approximately $30.

    View our post hotel recommendations

    Planning For Your Trip

    Traveling to Cuba

    We have an internal mantra of being “fun and flexible” at all times. It boils down to our guides being absolute rock stars when it counts and being able to handle any curveball thrown their way. On this trip, you may forgo some of the comforts you are used to on our luxury vacations. We invite you to adopt our mantra, keep an open mind, and enjoy what authentic Cuba has to offer before it is gone.

    Travel to Cuba solely for purposes of tourism is still illegal for Americans. In order to visit legally, you must meet one of 12 categories spelled out by the Treasury Department’s Office of Foreign Assets Control (OFAC). One of these categories is group people-to-people tours offered by tour operators. People-to-people exchanges are activities which facilitate meaningful interactions with Cuban people, giving you a better understanding of their lives and culture. You can rest assured that Trek Travel has incorporated people-to-people activities in each day of this trip, therefore traveling with us means your visit to Cuba meets with the requirements of U.S. law.

    We have listed our preferred hotels on our itinerary. Please be advised that these hotels are not guaranteed. We will notify you of the confirmed hotels you will be staying in the week before your trip. If you have any questions, please contact your Trip Consultant.

    Before and After Your Trip


    Before & After: Cuba

    Due to the legal restrictions on Americans traveling in Cuba, we do not recommend that you extend your trip. If you choose to do so, you must ensure that your travel meets the current legal requirements.

    Customer Reviews

    Why Trek Travel

    Our Bikes

    Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

    Our Guides

    Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

    Your Day. You Decide.

    Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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