Cuba Cycling and Culture Tour
On this 10-day cycling tour through the heart of the country, we will explore some of Cuba’s most vibrant communities, sparking coastlines and breathtaking countryside. Our adventure is designed for much more than just cycling and sightseeing, however. We aim to immerse you in Cuba’s rich culture and heritage as well, offering meaningful interactions with the local communities. Along the way we will meet and engage with artists, farmers, educators, restaurant owners, market vendors, and park guides to hear first-hand the stories behind the legend that is Cuba.
Start in Havana, exploring the northern side of the island for the first half of the tour. Then cross over to the Bay of Pigs to cycle to some of the legendary and historic locations on the south coast including Cienfuegos – a UNESCO World Heritage-listed town that has been dubbed the “Pearl of the South” – and colonial Trinidad. Snorkeling and kayaking are included. Return to the north side of the island on a ride over the Escambray Mountains.
PEDAL HAPPY! – ESSENTIAL CONSIDERATIONS FOR CUBA TRAVEL
Visiting developing countries can be eye-opening and life-changing, and hopefully visiting Cuba is both. Traveling within Cuba in particular requires a flexible attitude. Our days are full, and (as required by U.S. Law) we have a full-time agenda of activities to provide “Support for the Cuban People.” Cuba, however, has its own rhythm: things aren’t always open when they claim to be, and things don’t always run on time. We will endeavor to do our best to provide all of the content for the support program, but the specific activities and visits listed in our itinerary cannot be guaranteed.Similarly, accommodation and restaurants may not be up to the standards you are accustomed to. Sometimes the hot water or air conditioning doesn’t work. Restaurants may not have the same range of options you are familiar with, and so forth. Our guides promise to do their best to make this a fascinating and educational experience, but we also ask our guests to understand – as well as respect and appreciate – these differences in the people, food and culture. To fully understand these differences in detail you can contact our office for our Cuba Tour Info document with complete details about traveling to Cuba with us!
July 2, 2025 Update Regarding Travel to Cuba:
You may have seen recent news coverage suggesting that new travel restrictions to Cuba have been implemented by the U.S. government. We want to clarify that no actual changes have been made to current travel regulations. Feel free to contact our office if you would like more details about this.
Itinerary
Day 01
Meet, greet, and enjoy a welcome dinner in Havana.
Lodging
Grand Aston (Havana)
Meals
– Dinner
Arrive at Jose Marti International Airport in Havana (airport code: HAV) and take a taxi to our hotel, the Grand Aston in Havana. Airfare is not included. We will meet at the Grand Aston at 6pm for an orientation followed by a welcome dinner. Rest up afterward for a full day of exploration tomorrow!
Day 02
Museums, mosaics and classic cars. Tour colorful Havana!
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Grand Aston (Havana)
Distance
Urban “Hiking” – 4 miles or more.
Begin with a walking tour of the old city in the morning, followed by lunch. In the afternoon we visit the National Museum of Fine Arts focusing on the Cuban art section before heading to “Fusterlandia” – a neighborhood transformed by art and whimsy. Ride to dinner in a classic American car (1945-1956 era). Spend another night at the Grand Aston.
Day 03
Cycle to Santa Cruz del Norte and end the day in Matanzas – the “Athens of Cuba.”
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Velasco Hotel (Matanzas)
Distance
30 miles
Elevation
+1,086 ft / -1,167 ft
Begin cycling outside Havana. Pedal through farmlands and rural countryside on your way to Santa Cruz. End the day with a shuttle into in Matanzas, sometimes referred to as the “Athens of Cuba” due to its cultural heritage. Located where three rivers flow into the sea, Matanzas is lovely small city steeped in Afro-Cuban traditions. Explore the sights and art scene on a private tour before dinner. Stay at the Velasco Hotel.
Day 04
Matanzas loop ride, museum tour and dance performance.
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Velasco Hotel (Matanzas)
Distance
30 miles (4-5 miles on gravel)
Elevation
+1,022 ft / -1,014 ft
Shake out your legs on a morning loop ride through the foothills outside Matanzas. After lunch in town, we take a guided tour of the Museum of Slavery before attending a performance by and Afro-Cuban dance troupe. Have some free time to explore the city on your own before dinner. Stay another night at the Velasco Hotel.
Day 05
Ride inland from Matanzas and shuttle to Playa Larga on the south coast after lunch.
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Casa Particular (homestay) in Playa Larga
Distance
27 miles (6-7 mi. on gravel)
Elevation
+1,032 ft / -794 ft
Ride inland on quiet country roads in the morning and stop for lunch at a uniquely Cuban tropical farm and pottery production facility famous for its playful statues. After lunch we shuttle to the south coast (about 2 hrs) with a visit to the Korimakao artist’s community on the way. Tonight, we will be hosted by a Casa Particular (informal homestay) in Playa Larga, situated at the head of the Bay of Pigs.
Day 06
Cruise the coast, snorkel, visit the Bay of Pigs Museum, and transfer to Cienfuegos.
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Casa Particular, or Hotel Melia San Carlos (Cienfuegos)
Distance
Up to 49 miles.
Elevation
Up to +945 ft / -855 ft.
Cycle south along the Bay of Pigs coastline in the morning before veering inland to Yaguaramas. Enjoy snorkeling and a visit to the Bay of Pigs Museum on the way. Transfer (30min) to Cienfuegos for a walking tour of the famous city to get oriented before dinner. The “Historic Centre” has been designated a World Heritage Site by UNESCO for its stunning Neoclassical Caribbean architecture. Known as the “Pearl of the South,” the city is legendary within Cuba for its seaside promenade (malecón) and mansion-lined Prado (boulevard). Stay at a Casa Particular or Hotel Melia San Carlos.
Day 07
Cycle on the “colonial coast” from Cienfuegos to Trinidad.
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Casa Particular (Trinidad)
Distance
Up to 41 miles.
Elevation
Up to +1,739 ft / -1,774 ft.
Enjoy more coastal cycling today as we continue east to Trinidad, stopping for lunch by the sea at one of the beaches. The colonial city of Trinidad, founded in 1514, is one of the five original Spanish pueblos on the island, retaining many colonial buildings from the 18th and 19th centuries as well as the original cobblestone streets. Today it is a town of artists, history and culture – not to be missed! We will spend two nights in a Casa Particular and dine at a local paladar (home restaurant).
Day 08
Explore Trinidad, cycle to the beach, go kayaking, and have dinner on your own.
Meals
– Breakfast
– Lunch
Lodging
Casa Particular (Trinidad)
Distance
8.5 miles
Elevation
+127 ft / -314 ft
Take some time to explore Trinidad on your own in the morning before we hop on our bikes for a short pedal to Playa Ancon, one of Cuba’s most beautiful beaches. Enjoy the beach, have lunch, and then transfer (30 min.) to go for a lovely and leisurely kayaking trip (1.5 hrs.) on a tranquil river that offers fine birdwatching and fantastic views of Trinidad perched on the hill above. Return to Trinidad’s vehicle-free center in the late afternoon to visit a woman’s art cooperative. Dinner is on your own. There are plenty of restaurants to choose from, English is spoken, and they accept $US (cash only).
Day 09
Cross the Escambray Mountains to Santa Clara.
Meals
– Breakfast
– Lunch
– Dinner
Lodging
Hotel America (Santa Clara)
Distance
Up to 43 miles.
Elevation
Up to +3,505 ft / -3,189 ft.
The “Queen’s Stage!” Challenge your legs with a ride up and over the Escambray Mountains as we return to the north side of the island. Once a stronghold for revolutionary forces, these lushly forested mountains are filled with biodiversity. Do as much or little of the climb to the pass as you choose – we will be there to help. We often come across farmers working in their fields here. When appropriate, we stop to visit with them and learn about their lives. We finish the day and the tour in Santa Clara at Hotel America.
Day 10
Departure day from Santa Clara
Meals
– Breakfast
Departure from Santa Clara airport (code: SNU). Head to the airport after breakfast. Your guide can help you arrange a taxi (not included). American Airlines currently has two flights a day to Miami.
