Cuba: 10 days across the Isle of Freedom on legendary Harley-Davidsons with RMT and Ernesto Guevara

Book the tour - 13 Jan - 22 Jan 2026

We invite you on a 10-day motorcycle journey across the Isle of Freedom – a place familiar to everyone since childhood. This tour takes place on the legendary Harley-Davidson motorcycles, led by our main guide, Ernesto Guevara Junior, the son of the comandante Che.

We will show you a side of Cuba that most travelers will never see. You will experience it from the inside, immerse yourself in its culture and nature, and witness the beauty of this country and its people. Expect unforgettable adventures, meetings with locals, tours of historic sites, and the chance to savor an authentic Cuba Libre and cigars – all in great company, of course.

• Dates 2026: 13-22 January 2026
• Duration: 10 days
• Start/Finish point: Havana
• Total Distance: 1 600 km
• Difficulty Level: Intermediate
• Road Conditions: 100% asphalt
• Price with Harley Davidson – 6 250 EUR
• Single Room Supplement – 600 EUR
• Passenger Price – 3 500 EUR
• Deposit for the motorcycle 1 500 EUR 

The price includes:

• Transfer from and to the airport
• Guide professional assistance along the tour
• Harley-Davidson motorcycle rental
• Gasoline
• Support vehicle and replacement of a motorcycle for another one, in case of unforeseen circumstances
• Accommodation in 3-5* hotels
• Breakfasts in hotels
• Welcome and farewell dinners
• Full board in hotels "all inclusive"

The price does not include:

• Air tickets
• Additional activities
• Lunches, dinners and alcohol not included in the tour price
• Internet access throughout the route, except for internet access in hotels

Tour Route
Havana – Pinar del Río – Las Terrazas – Cienfuegos – Trinidad – Santa Clara – Cayo Santa María – Varadero – Havana

Day 1: Arrival, 0 km

Welcome to Havana! We will meet you at the airport and transfer you to a luxurious 5-star hotel. In the evening, enjoy a welcome dinner where you'll meet the team and guides.

Day 2: Havana, 80 km

After breakfast at the hotel, we’ll pick up our motorcycles and embark on a city tour of Old and New Havana. You'll immerse yourself in the city's rich history while visiting iconic landmarks such as the Malecón promenade, Revolution Square, Morro Cabaña fortress, and other fascinating sites. Lunch will be in the city.

Day 3: Havana – Pinar del Río, 340 km

We start the day with breakfast at the hotel before heading to Pinar del Río, Cuba’s renowned tobacco-growing region. Here, we’ll visit a traditional tobacco farm and enjoy an authentic Creole-style lunch. The ride continues through the stunning Viñales Valley, ending with an overnight stay in a charming 3-star hotel.

Day 4: Pinar del Río – Las Terrazas, 220 km

After breakfast, we ride toward Las Terrazas, a breathtaking nature reserve in the Sierra del Rosario mountains. Enjoy a scenic tour of the area, winding through picturesque mountain roads. Accommodation will be in a luxurious 5-star hotel.

Day 5: Las Terrazas – Cienfuegos – Trinidad, 330 km

We set off for Cienfuegos, also known as La Perla del Sur (The Pearl of the South), a picturesque colonial city. After a seaside lunch, we continue to Trinidad, a UNESCO World Heritage site and one of the finest examples of colonial architecture in Latin America. Accommodation will be in charming colonial-style hotels or private guesthouses.

Day 6: Trinidad, 100 km

Enjoy a guided walking tour of Trinidad’s historic center, followed by a scenic motorcycle ride through the breathtaking landscapes of the Escambray Mountains. We’ll explore unique viewpoints and hidden natural gems before returning to Trinidad for another night.

Day 7: Trinidad – Santa Clara – Cayo Santa María, 200 km

Today’s ride takes us to Santa Clara, where we’ll visit the Che Guevara Mausoleum. We then continue toward Cayo Santa María, crossing an incredible 60-km causeway that stretches across the ocean. Upon arrival, we check into a luxurious all-inclusive 5-star resort, where you can relax and unwind.

Day 8: Cayo Santa María – Varadero, 220 km

After breakfast, we ride to Varadero, Cuba’s most famous beach destination. Upon arrival, we check into a 4- or 5-star all-inclusive hotel. Enjoy a beachfront dinner and a relaxing evening.

Day 9: Varadero – Havana, 160 km

We begin our journey back to Havana, stopping in Matanzas and at Bacunayagua, the highest bridge in Cuba. Upon arrival in Havana, we check into a luxurious 5-star hotel and enjoy a farewell dinner.

Day 10: Havana – Departure