Lee's Cuba Bike Tours - Winter is Coming
Between January and March 2026, I’ll be leading two unforgettable bike tours through Cuba—and I’d love for you to be part of the adventure!
In this newsletter, I provide details on my second tour called Colonial Cities and Beaches which runs from February 21 - March 7, 2026. 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!
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Pina Colada at the Bacunayagua bridge |
The 2026 season will be based in Havana/Varadero, providing the option of flying into Havana or Varadero. Tour registration is open and encouraged - you can reserve a spot at no cost until Fall 2026. Don't wait too long, our first tour is already more than half full. With e-bikes becoming a big part of bike touring, Bicycle Breeze offers e-bike rentals and a large fleet of hybrid, gravel, road, mountain and tandem bicycles.
Colonial Cities & Beaches Tour
This bike tour begins in Havana, though you can also fly into Varadero if you prefer.
In Havana we will meet on the first evening for a dinner and introduce ourselves. The atmosphere in Havana is inspiring. The next morning we will have breakfast at our casa before heading off on the tour bus to begin our cycling vacation.
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Fine dining at Café del Oriente, Havana, Cuba |
After a bus ride, we will enjoy lunch at El Ranchon in Jagüey Grande a classic ranch-style open air restaurant. Then hop on our bikes, supported as always by a luxury tour bus, a cultural tour guide, a mechanic and me as the tour leader.
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Our amazing tour group of 2023 |
Our first destination is Playa Giron, where the failed Bay of Pigs invasion took place. We will stay at lovely casas in town and dine a short walk away at a private restaurant. Then 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. |
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 that is home to 285 types of palm trees and 2,400 species of plants. 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. After arriving in Trinidad and settling into our casas, we will explore the city maybe enjoying mojitos at famous Café de la Música.
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Café de la Música, Trinidad, Cuba
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A well-deserved and much-appreciated day at the beaches of Playa Ancon just 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 restaurant a la playa |
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As we depart Trinidad we will view the scenic Valle de los Ingenios (Valley of the Sugar Cane Mills) and explore Torre Manaca Iznaga. The astonishing view from this imposing torre (tower) more than justifies a short visit. Our ride will take us through the green lower hills of the Escambray Mountains before climbing to the village of Hanabanilla on 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 man-made lake. |
Leaving Hanabanilla behind, we will descend a gently road into 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) and defeated the government troops it carried. We will also tour the mausoleum commemorating Che and his fighters.
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Site of the battle of the armoured train sent by Batista in his final and unsuccessful attempt to win the Revolutionary War. Che defeated the army with a bold ambush after derailing the train |
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Che Guevara Mausoleum, Santa Clara, Cuba |
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Our tour groups support the Cuban people by donating cycling equipment to youth clubs |
The next leg of the cycling journey will take us through the tobacco country to Remedios on a gently rolling road. The central square is beautiful. The Iglesia Major church is the oldest one in Cuba, with a gold leaf altar which was hidden from pirates for many years.
Our next bike ride brings us to Caibarién, a colourful fishing town called “La Villa Blanca” (The White Town) for its white sand beaches. After checking out the town and its recently built malecon, we will board our bus to travel the causeway to the beautiful beaches of Cayo Santa María. Cubans consider this the best beach in Cuba as the white sand is so fine (like sifted white flour) that it doesn't even get hot in the midday sun.
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Great pool for cooling off |
From Cayo Santa María our tour bus saves us time and effort by driving us to Colón, a small town with neoclassical architecture and an impressive statue of Christopher Columbus guarded by four lions. Then we cycle to Matanzas most likely with the wind at our backs. I remember our time in the Village of Coliseo in 2023 where we hunted for drinks and snacks. In the end, we got beer, pop, and ate our snacks at a small shop operated out of some guy's front yard, with us paying him over his front gate. Good times!
Our tour bus will take us back to Havana where we began our adventure. We will spent a day touring the grand city. A description of all the sights would take far too long in this blog post. At night we had a tasty dinner on the top floor of the FOCSA building.
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The Capital Building in Havana is based on the American Capital Building but one-metre taller |
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Our view from La Torre Restaurant situated on the 34th floor of the tallest building in Cuba
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We will have a chance to say goodbye to our new friends at the end of the tour before we return home. What a great adventure with so much fun, good exercise and 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 aclimatize to Cuba or further explore this exceptional city.
My 2026 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.
So let's explore the two tours I will be leading in 2026
Fat Mary (Maria la Gorda) 2026
When: January 31 to February 14, 2026.
A fully-supported 15-day tour of Western Cuba.
A popular ride on the quiet back roads of western Cuba, taking its name from our destination at Maria la Gorda. 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, and stay at several beautiful white-sand beaches.
For more details or to register for this tour head to the website
Fat Mary WebsiteColonial Cities & Beaches Tour 2026
When: February 21 to March 7, 2026.
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
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. 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 just 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. 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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