Lee's Cuba Bike Tours with Bicycle Breeze
Between January and March 2027, I’ll be leading two unforgettable bike tours through Cuba—and I’d love for you to be part of the adventure! And, yes, it is still possible to run a successful tour this winter as we have secured a supply of fuel for the bus, and accomodations. Food is readily available for tourists. Cuba needs support from tourists as we bring money to the Cuban people who need it to buy their own food and pay the bills.
In this newsletter, I provide details on my first tour, Colonial Cities and Beaches, running from January 30 to February 13, 2027. Our amazing support team will ensure you enjoy sunshine, cycling, and Cuban charm.
Let’s make next season even more amazing—hope to see you on the road!
The 2027 season will be based in Havana as there are a dozen flights daily. Tour registration is open and encouraged - you can reserve a spot at no cost. With ebike demand exploding, Bicycle Breeze offers ebike rentals along with a large fleet of hybrid, gravel, road, mountain and tandem bicycles.
2027 Bike Tour Options
My 15 years of experience touring Cuba by bike enables me to ensure your safe enjoyment of Cuba, so you can have a healthy and relaxing bike tour exploring this beautiful island. I pride myself on making sure riders are well prepared for their adventure in Cuba and have no surprises.
Below is a summary of the two tours I will be leading in 2027.
Tour #1: Colonial Cities & Beaches
When: January 30 to February 13, 2027
A fully-supported bike tour of Central Cuba focused on its rich culture, natural beauty, friendly people and quiet roads. This tour explores Cuba's best beaches and most historically significant colonial cities.
- Havana the capital and UNESCO World Heritage site
- Cienfuegos the French-inspired “Pearl of the South”
- Trinidad with its cobbled streets
- Santa Clara home of the Mausoleum to Ché Guevara
- Remedios a charming colonial city
- Matanzas the city of rivers and bridges
Tour #2: Gringo Viejo
When: February 20 - March 1, 2027
A fully-supported 10-day tour of Western Cuba.
Join us on this popular ride on the quiet back roads of western Cuba. We will explore Havana and ride in classic cars. Be amazed by the UNESCO-recognized Valle Viñales with Cuba’s tobacco lands. Enjoy guided tours of orchid gardens, historical sites, caves, coffee and tobacco farms.
Colonial Cities & Beaches Tour Travelogue
I want to share a story of this fun bike ride.
After transferring from the Havana airport to our casas particulares (BnBs) we will meet on the first evening for dinner. The atmosphere in Havana is inspiring and reminds me of being in a European city. The next morning, we will have breakfast before heading off to begin our cycling vacation.
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| Dinner in Havana |
We will enjoy lunch at El Ranchon in Jagüey Grande, a classic ranch-style open-air restaurant; then hop on our bikes, supported by a luxury tour bus, a cultural tour guide, a mechanic and me as the tour leader. Our first destination is Playa Giron, the site of the failed Bay of Pigs invasion. We will stay at lovely casas in town and dine a short walk away at a private restaurant. We will cycle along beautiful country roads to the first colonial town of this tour, Cienfuegos, the lively, seaside “Pearl of the South” with its French-inspired grand boulevard and colonnades.
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Looking out from our rooftop bar at the Hotel La Union, Cienfuegos, Cuba
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Next on our exploration of colonial cities, we ride some rolling hills into Trinidad. But first, we will visit the Jardín Botánico de Cienfuegos, an outstanding botanical garden stocked and maintained for many decades by Harvard University. Beyond the garden, the road heads down to the coast, giving glimpses of the Caribbean and the upland pine forests of the Sierra Escambray mountains.
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Café de la Música, Trinidad, Cuba
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A well-deserved and much-appreciated day at Playa Ancon 10 kilometres south of Trinidad, will restore our energy for the rides ahead.
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| Playa Ancon - white sand, shade trees, and a great beach restaurant |
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Departing Trinidad, we will view the scenic Valley of the Sugar Cane Mills and explore the Manaca Iznaga Tower. Our ride will take us through the green lower hills of the Escambray Mountains, then on to the banks of Lake Hanabanilla. A guided forest walk in the morning will be followed by a boat trip to the other side of the lake for lunch.
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| Hotel Lake Hanabanilla, with a spectacular view of the lake. |
Our next ride takes us to the City of Santa Clara where we will visit the battle site where Che Guevara and a small number of men essentially ended the Cuban Revolution by derailing the Tren Blindado (Armoured Train). We will also tour the mausoleum commemorating Che and his fighters.
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| Che Guevara Mausoleum, Santa Clara, Cuba |
The next leg of the cycling journey will take us through the tobacco lands to Remedios on a gently rolling road. The town's Iglesia Mayor church is the oldest one in Cuba, with a gold leaf altar which was hidden from pirates for many years. Caibarién is a colourful fishing town known for its white sand beaches. After checking out the town and its malecon, we will visit Cayo Santa María. Cubans consider this the best beach in Cuba as the white sand is so fine that it doesn't even get hot in the midday sun.
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| Great pool for cooling off |
After travelling by bus to Colón, we cycle to Matanzas most likely with the wind at our backs. Our tour bus will take us back to Havana, where we began our adventure. We will spend a day touring the grand city and have a ride along the Malecón in a vintage car. A description of all the sights would take far too long in this blog post.
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| The Capital Building in Havana is based on the American Capital Building but one-metre taller |
We will have a chance to say goodbye to our new friends during dinner at one of Havana's fine restaurants. What a great adventure with so much fun, good exercise, food, and a cultural experience beyond belief.
I'm happy to spend a few days before or at the end of our tours in Havana with anyone who wants time to acclimate to Cuba or further explore this exceptional city. Extra days at a casa are inexpensive at about $35-40 USD per night.
What’s Happening in Cuba Right Now?
Cuba depends on tourism to obtain hard currency from developed countries to buy 80% of its food on the world market. Our tours directly support Cubans who work in the tourism industry through wages and tips from clients. Our tours also support Cuban youth cyclists as we, along with our riders, bring thousands of dollars of cycling equipment to the school programs in each province of the country, along with medicine and clothing. This enables our American riders to meet the US rules for "supporting the Cuban people".
Cuba is not always able to generate enough electricity due to aging equipment. This is sometimes managed by turning off power to certain neighbourhoods, usually for a few hours, sometimes for longer. I manage this by bringing rechargeable flashlights and a power bank to recharge my phone. Almost all hotels, and most casas, have backup power generators, so for us, this is mostly a periodic inconvenience.
Food for tourists has been readily available, and meals at restaurants, hotels, and casas particulares (Cuban B&Bs) have been simple but tasty. We wish it were easier for Cuban Nationals to obtain their groceries and have a consistent supply of electricity. More tourists are the biggest opportunity to help Cuba financially.
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| Hearty Breakfast at a casa particulares |
Final Words
Thanks for reading!
Feel free to share this newsletter with friends or fellow cyclists who might be interested. If you have any questions or want more details, don’t hesitate to reach out—I’m happy to chat or set up a Zoom call for individuals or groups. I can also send you a brochure with daily itineraries, photos, and everything you need to know about the tours.
Looking forward to riding with you!
Lee Orphan
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