motorcycle tours cuba harley tourmotorcycle tours cuba harley tour
fly ride cuba motorcycle diaries harley tour 2017-12-04T18:23:39+00:00





MARCH 6TH – 14TH 2018

MAY 7TH – MAY 15TH 2018

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.

Highlights of the tour

  • Ride one of a range of brand new Harley Davidsens
  • 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
cuba motorcycle diaries tour city
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)
Book now



Motorcycle Diaries 5* Harley Tour

Paved tour

9 days

1 Country

From £3499

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 / 50 miles 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 / 230 miles Ride along the coast to Giron beach the site of the 1961 US invasion, tour around Cienfuegos city and then ride on towards the UNESCO World Heritage Site of Trinidad.

Day 4 / 125 miles Head towards Santa Clara via Topes de Collantes or Yaguajay and then ride along the stunning causeway that links the Cayo to the rest of the island. Your afternoon is free today to explore the sites and your dinner is at your 5* hotel.

Day 5 / 75 miles This morning is for relaxing on the beach before hopping back onto the bikes and cruising over to Santa Clara, with a city tour of the historical town of Remedios on route. After lots of pics of the colonial architecture here you can visit the Che Guevara Mausoleum and Armoured train to top off the day.

Day 6 / 125 miles 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 7 / 95 miles Some more time to enjoy the beach this morning before setting off and then a cruise back towards Havana. Your midday stop today includes a visit to Matanzas before making your way to your 5* hotel and a free evening to explore the local area.

Day 8 / 110 miles 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 your farewell dinner.

Day 9 / Breakfast at your hotel and free time to explore the city before an included transfer to the airport for your flight home.

motorcycle holidays in cuba seafront motorcycle holidays in cuba hotelmotorcycle holidays in cuba rider
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,
motorcycle holidays in cuba train
motorcycle holidays in cuba road
It’s been an unforgettable experience and we leave knowing we have learned a lot and made some great friends.
Bridget & Joe (New Zealand),
motorcycle holidays in cuba bikes

What’s included

  • 8 Nights accommodation in a variety of 5* hotels and Luxury private houses, all your meals on riding days, dinner on arrival and breakfast on your final morning.
  • Bi-Lingual local tour guide
  • Choice from a fleet of brand new Harley Davidsens 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.
  • Airport transfers

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 30% deposit per person at the time of booking. The balance payment is due 10 weeks before the commencement date.

  • Two people – One bike shared room £3499pp

  • One person – One bike shared room £4199pp

  • One person – One bike single room £4999pp

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.

Book now
all tours

Signup to our newsletter for all the latest offers

Your Name (required)

Your Email (required)

Why not follow us on social media for more exclusives?


But Offers On Our Newsletters Can Sometimes Include FREE Spending Money, 10% OFF Tours, Last Minute Spots and More!

Join the other riders on our mailing list for access to exclusive offers, news and info on our latest tours.

Sign up or decline, either way you’ll never see this pop up again!