Cuban Highlights Ride

Cycle the Pearl of the Caribbean, experiencing the best bits and discovering a nation forged under unique circumstances

Cuban Highlights Ride

Let's Call You

Trip Fee

$ 2.520

Single Room Difference

$ 353

Date

08 - 15 November 2025

Trip Information

Explore Cuba by bike, the ideal way to immerse yourself in a beautiful island shaped by revolution and resilience. Cycling through lush countryside, vibrant colonial towns and quiet coastal roads, we enjoy countless interactions with the welcoming local people: dancing salsa, riding with cycling club members and cruising through Havana in a classic car. Of course, there’s revolutionary history to discover, the UNESCO-listed towns of Cienfuegos and Trinidad to explore, and the chance to enjoy a fresh mojito at the end of a day’s cycling.

Activity Areas

Cycling
Road Cycling

Region & Country & City

Central America: Cuba, Havana, Trinidad

Included in the Price

— Seven breakfasts, six lunches, three dinners — All accommodation — All transport and listed activities — Tour leader throughout — Arrival and departure transfers — Local bike hire — Cuban tourist card for most UK/Ireland residents

Not Included In The Price

— Travel insurance — Single accommodation (available on request) — Visas or vaccinations

Accommodation Information

— Accommodation: 7 Classic nights (Cuban guesthouses known as Casa Particulares) — Six days of cycling with full vehicle support — Group normally 4 to 18, plus leader. Minimum age: 16 — Tour enables legal travel to Cuba for US citizens under the Support for Cuban People program

Map

Itinerary

Day 1 Start Havana

Welcome to Havana, the lively capital of Cuba. Founded by the Spanish in the 16th century, it is now a soulful mix of colonial architecture, street troubadours and classic cars. Meet your tour leader and fellow passengers today at the start accommodation. Accommodation: Casas particulares

Day 2 Havana cycle tour • To Playa Larga and the Bay of Pigs

After a bike fitting, we have a cycling tour of Havana with a member of the Cuban Masters Road Cycling Club. This club is made of veteran Cuban cyclists who regularly compete in races in their respective age groups. Arriving into the Old Town, we stop for a cafecito (Cuban-style coffee) at a privately owned café, which also offers snacks and drinks. Later, we transfer to Playa Larga and stay overnight at the Bay of Pigs. During dinner at a small beachfront restaurant specialising in freshly-caught fish, we are joined by a local nature expert who introduces us to the natural landscape and characteristics of the area. We round the evening off in a classically Cuban manner, with rum and a few rounds of dominoes. Accommodation: Casas particulares

Day 3 Coastal cycle ride • To Cienfuegos

Our day begins with a coastal cycle ride from Playa Larga to Playa Girón, where we stop for a breather and an explanation of the US' failed Bay of Pigs invasion in 1961. We continue the ride to Caleta Buena on the coast for lunch and a swim, before transferring to Cienfuegos. The city of Cienfuegos is full of architectural delights, with a beautiful main square and restored buildings. We tour the city by e-tricycle, fun tuk tuk-like vehicles that can accommodate four people and run on solar power. Used locally as public transport, they provide an authentic way to see the city. After, we check into our casas for the night. They are close to the town centre and some great paladares (traditional restaurants). The malecon coastal road is usually a lively place to soak up the atmosphere with locals. Accommodation: Casas particulares

Day 4 Ride from Cienfuegos to Cumanayagua • To El Nicho Waterfall

On today’s ride, we are joined by at least one master cyclist from the Cienfuegos cycling team; there is plenty of time to chat before and during the ride at the various pitstops. This morning, we cycle from Cienfuegos to Cumanayagua before transferring to El Nicho Waterfall. We have a short walk to the waterfall, where we can relax and enjoy a swim in the natural pools. Lunch is at a paladar next to El Nicho. In the afternoon, we return to Cienfuegos by bus. For those interested, there is the option to do a more challenging ride and cycle all the way to El Nicho Waterfall (additional distance of 14mi/22km, ascent 2,238ft/682m, descent 1,053ft/321m). Accommodation: Casas particulares

Day 5 Cycle to Rancho La Vega Farm • To Trinidad

We're joined again by at least one master cyclist from the Cienfuegos cycling club to ride from Cienfuegos to Rancho La Vega, an interesting farm where we have lunch. We transfer by bus to Trinidad, declared a World Heritage site in 1988 and perhaps the best-preserved colonial town on the island. Exploring Trinidad can feel like entering a time warp, the cobbled streets and horse-drawn transportation whisking us back. There are many interesting museums housed in old colonial buildings and music drifts through the streets and plazas, bringing the town to life. In Trinidad, we have a walking orientation of the town and dinner at a paladar. Accommodation: Casas particulares

Day 6 Cycle to Playa Ancón and back; optional salsa class in Trinidad • Visit Casa de la Trova

This morning, we cycle to Playa Ancón, a classic white-sand Caribbean beach where we have time to relax, eat lunch in a beach paladar, and enjoy the sea. We have a short cycle back to Trinidad where there is time to rest or explore the cobbled streets and visit local businesses. In the evening, there is the option to take part in a salsa class with Cuban dance partners. Trinidad is known for its nightlife, so after we’ve learnt the salsa basics, we head to Casa de la Trova, a legendary live music venue, to listen to local musicians playing authentic Cuban music. This venue is always lively and sociable, with plenty of Cubans keen to let us practise our dancing with them! Accommodation: Casas particulares

Day 7 To Havana via Valle de los Ingenios and Santa Clara

This morning, we have short ride from Trinidad to Rio Seibabo in the heart of the Sierra del Escambray mountain range. En route, we stop at Manaca Iznaga market in the Valle de los Ingenios to meet textile makers and sellers, and we also speak with lace makers at Proyecto Manacú, a female-led initiative that aims to keep traditional textile-making methods alive. Our next stop is at a farm where we are introduced to a local farmer and his family who make delicious honey. We then transfer to Santa Clara, the first major city to be liberated by Castro’s army in December 1958. Today, several monuments commemorate this important period, including the mausoleum of Che Guevara, where we stop for a short visit. Afterwards, we transfer back to Havana. This evening, we have dinner at a private paladar in Havana. Accommodation: Casas particulares

Day 8 Classic car tour and sightseeing in Havana • To the airport

This morning, we see Havana in style – by classic car. Havana is one of the finest colonial cities in the Americas with narrow streets, spacious plazas and glorious architecture, and there is an air of faded grandeur about the place. Visiting both the old and new areas, we discover the distinct areas of the capital, stopping at points of interest. Feel free to ask why the streets of Cuba are filled with classic American cars manufactured in the 1950s and how the owners manage to maintain them! Afterwards, we have a walking tour of UNESCO-listed Old Havana, the heart of the capital. Old Havana is often described as a living museum, with magnificent monuments, cathedrals and palaces. During our tour, we visit a ration store and food market for a glimpse into daily life in the capital. It’s then time to bid your group and leader a fond farewell as this marks the end of our Cuban two-wheeled adventure.

Travel Dates

08 - 15 November 2025 $ 2.520

20 - 27 December 2025 $ 3.000

14 - 21 March 2026 $ 2.415

24 - 31 October 2026 $ 2.700

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