Photo: Ivan2010 ↗THE JOURNEY IN DETAIL
An island on its own clock.
A loop from Havana: the tobacco valley of Viñales with its mogotes, the south coast, colonial Cienfuegos, cobbled Trinidad and Santa Clara with the Che memorial. Cuban roads are half-empty but full of potholes, horses and bicycles, so the pace is slow and the distances short. A tour more about the country than the corners: casas particulares, music in the evenings and the old Harleys locals have kept running since the 1950s.
- The Viñales valley and its mogotes at dawn
- Havana’s Malecón on two wheels
- Trinidad and the Valle de los Ingenios
- The Che Guevara memorial in Santa Clara
With old friends or new ones
Join a group or arrange a separate departure for your own team. Before travelling, we get to know each other, discuss everyone's experience and find suitable dates. You can also prepare together.
DAY BY DAY
Your daily itinerary.
A provisional itinerary. Weather, group readiness and local conditions may change the order and length of the stages.
- DAY 1 · The city
Havana
Arrival, check-in in Old Havana and an evening walk along the Malecón. No bikes yet: a day to catch the rhythm of the city.
Overnight: Casa in Old Havana - DAY 2 · 60 km, the city
Bikes and the Malecón
Bike collection and fitting, then a lap of Havana: the Malecón, Vedado, the Plaza de la Revolución and the Morro fortress. About 60 km in the city.
Overnight: Casa in Old Havana - DAY 3 · 200 km, the valley
Las Terrazas and Viñales
West along the motorway and through the coffee plantations of Las Terrazas in the Sierra del Rosario, then Pinar del Río and the descent into the Viñales valley. About 200 km.
Overnight: Casa in Viñales - DAY 4 · 120 km, the beach
Tobacco, caves and the valley loop
A morning on a tobacco farm, then a loop of the valley: the Cueva del Indio, the Mural de la Prehistoria and the road to Cayo Jutías beach on the north coast. About 120 km.
Overnight: Casa in Viñales - DAY 5 · 350 km, the motorway
The Bay of Pigs
The longest day: east along the motorway past Havana, via Jagüey Grande to the Zapata swamps and Playa Larga on the Bay of Pigs. Evening snorkelling at Playa Girón. About 350 km.
Overnight: Casa in Playa Larga - DAY 6 · 170 km, the coast
Cienfuegos and Trinidad
Along the coast to Cienfuegos with its French street grid and the Punta Gorda waterfront, then the coast road beneath the Escambray to Trinidad. Evening at the Casa de la Música on the steps. About 170 km.
Overnight: Casa in Trinidad - DAY 7 · 100 km, the Escambray
Topes de Collantes and the sugar valley
The steep road up into the Escambray to Topes de Collantes at 800 m, waterfalls and coffee, then the Valle de los Ingenios with the Manaca Iznaga tower. About 100 km.
Overnight: Casa in Trinidad - DAY 8 · 340 km, bikes returned
Santa Clara and back to Havana
Via Sancti Spíritus to Santa Clara for the Che memorial and the armoured train, then the motorway west to Havana. Bikes returned and a farewell dinner. About 340 km.
Overnight: Casa in Old Havana - DAY 9 · Departure
Departure from Havana
Breakfast and a transfer to José Martí airport.
Overnight: —
Included in the estimated price
Harley-Davidson Heritage Softail or Royal Enfield Himalayan hire
8 nights in casas particulares and boutique hotels with breakfast
A support vehicle with mechanic and reserve fuel
Local guides and a lead rider
Dinners with the families at the casas
A tobacco farm visit in Viñales
Not included in the price
Flights to the meeting point
Personal travel insurance and visas
Personal equipment
Single-room supplements and personal expenses
Fuel
Lunches
The Cuban tourist card and compulsory medical insurance
Single supplement
YOUR PREPARATION
Arrive ready for the route.
A category A licence and at least 5,000 km; the riding is simple and attention matters more than speed. Ivan explains the realities of Cuban roads, fuel supply and connectivity, which is not always available.
Prepare with IvanROUTE QUESTIONS
BEFORE WE MEET ON THE TRAIL
What to prepare in advance
- Full riding kit: helmet, protection, gloves and boots
- Rain gear and waterproof covers
- Documents and insurance for your chosen riding format
- Compact soft luggage without unnecessary weight
Once we choose a date, we agree on the equipment list, meeting point and transfer time. Please wait until the programme is confirmed before booking flights.