motorcycle tours cuba harley tour
fly ride cuba motorcycle diaries 10 day harley tour 2018-11-07T16:53:28+00:00




December 2nd – 11th 2018

January 23rd – February 1st 2019

March 1st – 10th 2019

May 7th – 16th 2019

October 13th – 22nd 2019

December 4th -14th 2019

These tours will be led by Ernesto Guevara

The Cuban tours are the only trips on the Magellan menu that aren’t run in house by one of our own guides, why is that you may ask? Well as much as we’d love to be the Cuba pros on this one we think that Che Guevara’s son Ernesto deservedly pulls rank here in the tour guiding stakes so we hand the reigns of our Cuban trips over to him and his team at La Poderosa tours.

We love riding over there with him and Camillio, the weather is amazing, the bikes epic and the country needs to be ridden through to be truly experienced so we’re really proud to act as their UK agent on these fantastic trips.

Ernesto and his friend Camillo will lead your trip in person with riders joining you from all over the world, our Motorcycle Diaries 5* Harley Tour truly is a once in a lifetime ride. Follow the sights and locations of one of the world’s most famous travelogues, taking time to enjoy both the culture and welcoming people of this undefinable country.

Only recently awaking from an economic embargo that has lasted 50 years you will experience all the iconic images that Cuba conjures up and more. From the shabby facades to the bustling streets of the colonial era cities, the white sands of the caribbean beaches to the UNESCO world heritage sites of Havana, Trinidad and Cienfuegos, this trip has it all. With all your meals covered on the trip the only thing you need to budget for is flights, fuel and cigars to bring home with you!

Highlights of the tour

  • Ride one of a range of Harley Davidsons

  • The Malecon Habanero, Plaza de la Revolution and Che Guevara’s Command Headquarters
  • Relax on a selection of caribbean beaches
  • Visit UNESCO World Heritage Sites of Havana, Trinidad and Cienfuegos
  • Sierra del Rosario Nature Reserve and Soroa Orchid farm
  • Colonial town of Remedios, the Che Guevara Mausoleum and Armoured train
  • 5* Hotels and Luxury private houses
The motorcycle we had reserved, a Harley Davidson Ultra Glide was new, clean and in perfect mechanical condition.
We could see many things, we met lovely people and we realized that we were in the correct tour with the right people: it was very special to be able to have Ernesto and Camilo as guides. With them we got to know places unknown to tourists.

I am sure that we will come back to Cuba because we arrived as strangers and now we leave behind friends who we must visit again.

Ebbes (Germany)
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Motorcycle Holidays in Cuba: 5* Tour Itinerary

Day 1 / Airport pickup from the VIP lounge at Jose Marti International airport. Queue jump at immigration and baggage reclaim as well as complimentary drinks. Transfer to your 5* hotel and settle in for dinner to relax and unwind after your flight.

Day 2 / City tour of Havana on to get familiar with your chosen motorcycle, visiting the Malecon Habanero and Plaza de la Revolucion. In the afternoon you can also take a tour of Che Guevara’s Command Headquarters before checking in to your second luxury hotel for the evening.

Day 3 /  Leave Havana towards Viñales the land of tobacco farms and visit a working plantation.

Day 4 /  Today we ride to Las Terrazas Community in Sierra del Rosario Nature Reserve and spend time down by the river at San Juan. We visit the Soroa Orchid farm and have lunch at a great local Creole spot. The afternoon takes us all the way back into Havana for another overnight stop.

Day 5 / Leave towards the UNESCO world heritage site of Trinidad via Cienfuegos.

Day 6 / City tour of Trinidad and time to explore the local area around Lola.

Day 7 / Visit the Che Guevara Mausoleum and Armoured train on the way to Cayo Santa Maria and ride the famous causeway to your 5* hotel.

Day 8 / A beautiful day’s ride today toward Varadero with a stop off for a panoramic city tour of Cardenas. The evening is spent in another fine 5* hotel

Day 9 / Return back towards Varadero but this time from the northern scenic road and onto Havana for your final night.

Day 10 / Breakfast at your hotel and free time to explore the city before an included transfer to the airport for your flight home.

As well as riding past the ubiquitous images of Che Guevara painted on billboards across the island, tour highlights include visits to places connected to the revolutionary: the Comandancia del Che (a small museum dedicated to him) at the monumental 18th-century Cabaña fortress at Havana’s harbour, where Che had his headquarters; and Che Guevara’s mausoleum in Santa Clara.
Claire Boobayer,
It’s been an unforgettable experience and we leave knowing we have learned a lot and made some great friends.
Bridget & Joe (New Zealand),

What’s included

  • 9 Nights accommodation in a variety of 5* hotels and Luxury private houses, all your meals are included too.

  • Led by Ernesto Guevara and his friend Camillo

  • Choice from a fleet of Harley Davidsons and full insurance.
    (V-Rod, Sportster, Electra/Street/Wide Glides, Street Bob, Low Rider and Switchback)

  • Air-conditioned support vehicle for travellers and their luggage, a complete tool kit and spare parts and spare motorcycles also accompany our journey just in case.

  • Breakfasts, lunches and dinners both in restaurants and “paladares” (private restaurants in Cuba) as well as beverages and fresh produce all included.

  • VIP Airport transfers wisk you through security in style.

What’s not

  • Airfare and Visas (cheap flights can be found on SkyScanner)
  • Riding gear (trousers, jacket, helmet, gloves). We recommended you bring your own gear if you have it, however if you need to borrow some let us know and we can always help to arrange some.
  • Travel / Medical Insurance
  • Alcoholic beverages
  • Fuel


  • We require a £1500 deposit per person to secure your booking. The balance payment is due 10 weeks before the commencement date.

  • Two people – One bike shared room £3295pp

  • One person – One bike shared room £4095pp

  • One person – One bike single room £4495pp

more harleys on our motorcycle holidays in cuba

For more information on what to get prepared before your trip, what insurance to sort as well as the answers to many frequently asked questions see the “before you go” section at the top of the page.

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