Active & Adventurous

If your perfect holiday involves endless energy, adventure and exciting experiences rather than lying on a beach, Cuba is the perfect choice for the thrills and spills of an action-packed holiday.

If your perfect holiday involves endless energy, adventure and exciting experiences rather than lying on a beach, Cuba is the perfect choice for the thrills and spills of an action-packed holiday.

Whether it’s dancing the night away in Havana, biking through spectacular landscapes, snorkelling and diving over crystal clear reefs, climbing mountains in the footsteps of Che Guevara, hiking through coffee plantations, camping under the stars, sailing to desert islands, zip wiring through the trees, or a host of other exhilarating activities then this vibrant and friendly island has it all.

Whatever your appetite, our multi-activity holidays can be carefully tailored to suit your interests and energy levels. And best of all if you are travelling with others who are less energetic or with a milder hunger for adventure, we can combine the best of both worlds so you enjoy an active holiday whilst they take a slower pace. Of course, there are always Cuba’s world class beaches to head to for an end of holiday relax!

Tailormade Adventure Holidays

Tailor-Made Activity, Sports, and Special Interest Holidays. Many of our clients prefer an entirely bespoke journey to Cuba, meticulously crafted around their interests, time, and money

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Cuba Holidays for the Active and Adventurous. Sample Itineraries

For those looking for an action-packed holiday,  we’ve hand-picked eight destinations that should give you plenty of choices to organise something really special while keeping costs in check. How you mix them is entirely up to you.

Some of our clients prefer a longer stay by the beach; others prefer to skip Varadero altogether to spend more time in Trinidad or the beach. The unspoiled beaches of Cayo Levisa are increasingly popular. Trinidad is such a charming colonial town surrounded by verdant mountains and the  sea, that is not uncommon our clients ask us to make the arrangements for them to stay there a few nights and enjoy the lively town culture. Vinales boast the best of Cuba’s countryside. And Santiago de Cuba is, in many ways, the cradle of Cuban culture.

When you speak to us, we can discuss your interests and expectations and suggest the best itinerary based on your plans for this trip

Matthew Osullivan, Captivating Cuba


Adventure holidays we’ve created for our clients in the past include some of the following variations

  • Havana + Varadero
  • Havana + Santiago + Sierra Maestra + Baracoa
  • Havana + Vinales + Las Terrazas National Park + Varadero
  • Havana + Vinales + Las Terrazas National Park + Trinidad + Varadero
  • Havana + Vinales + Las Terrazas National Park + Trinidad + Sierra Maestra + Santiago + Baracoa

Continue reading our recommended accommodation and experiences in each destination. These include our top-recommended resorts and activities we think you will love.


Adventure Holiday Cuba, by Captivating Cuba™

A guided cycling challenge through the streets of Havana, exploring the back streets of this unique city on two wheels

Join the locals with a guided run along the Malecon and past Old Havana’s famous sights, a great energetic way to see the city

Take our Revolutionary challenge through the streets of Old Havana with lots of activities, prizes and great fun!

Enjoy a fun and professional Salsa lesson with excellent teachers and your own local dance partner

Varadero Beach

Take your own catamaran for a day cruising the clear blue waters off the coast of Varadero, with stops for snorkelling and swimming, lunch and lots of fun

Enjoy an exhilarating jeep safari through the back roads with snorkelling at Coral Beach, swimming in the cool natural pools at Saturno cave and a leisurely boat ride along the Yumuri river

Pre-book your tee off time at the Varadero Golf Club and enjoy this challenging 18-hole links course

Take a private boat out into the Gulf of Mexico for a day of deep sea fishing, with the support of a local crew and drinks on board it’s an exhilarating day

Ride the waves and enjoy dedicated tuition with a series of kite surfing lessons a excellent challenge in the warm Varadero waters

Valley of Vinales

LGBT Holidays Cuba. Captivating Cuba™

Take a walk along the virgin beach and snorkel in the clear waters at the beautiful island of Cayo Jutias, dining on the fresh seafood catch of the day

Explore deep into the limestone caves complex one of the largest in the Americas with as local caving guide

Watch the sun rise over the valley on your early morning bike or horse ride returning in time for a hearty breakfast

Spend a day exploring the quiet back roads and paths, snaking through the spectacular Karst scenery with a full guided biking tour

Trek to the top of one of the famous Mogote mountains and marvel at the views below

Las Terrazas National Park

Adventure Holiday Cuba, by Captivating Cuba™

Take an early morning trek to the summit of El Taburete with its monument to Che Guevara, returning for a swim in the San Juan river before breakfast

Enjoy the thrill of a birds-eye view over the Las Terrazas community on the largest zip wire ride in Cuba

Cycle through the Sierra De Rosario hills by bike to Soroa and visit the waterfall with the chance to swim in the river pools before returning by bike

Horse ride through the Las Terrazas National Park with a local guide and learn a little more about rural life in Cuba

Trinidad, Cuba.

Adventure Holidays Cuba

Visit the beautiful Escambray Mountains on a jeep safari. Enjoy a swim in the cool waterfall pools and learn about life in the mountains with lunch at a local farmer’s house

Scuba Dive or snorkel in the warm waters of the Caribbean Sea close to Trinidad

Learn to cook Cuban style in the heart of historic Trinidad. A local chef can guide you through the menu of a traditional Cuba feast, with one or two mojitos to keep you going

Cycle along the undulating road to Sugar Mill Valley or into the Escambray mountains for the more challenge minded cyclist

Sierra Maestra

Adventure Holiday Cuba, by Captivating Cuba™

Visit the revolutionary camp at La Plata, situated deep in the Sierra Maestra mountains and see how Che, Fidel and their followers started the Revolution

Trek to Cuba’s highest peak in the footsteps of the Revolutionary heroes with an overnight in a mountain lodge, before an early morning summit of Pico Turquino

Trek through the forests along the mountain river past small hamlets and farms, swim in the river pools and marvel at the mountain scenery

  • Villa Santo Domingo

  • Carefully selected recommended casas particulares


LGBT Holidays Cuba. Captivating Cuba™

Explore at your leisure the oldest and most picturesque spot in eastern Cuba. This historic town was the first Spanish settlement in Cuba (the first Villa), founded in 1511. It is also the spot where the Spanish conquistadors, lead by Colombus, first touched land in Cuba back in 1492.

  • A carefully selected recommended casas particulares

  • 2* El Castillo

Santiago de Cuba

LGBT Holidays Cuba. Captivating Cuba™

Dance the night away at the world famous cosy Casa De La Trova in the heart of the city centre

Head to the mountains at Gran Piedra and spent the day trekking in the rolling hills

Walk through the vibrant city to the Santa Ifigenia cemetery and visit Fidel Castro’s Mausoleum, followed by a tour of this unique revolutionary cemetery

  • A carefully selected recommended casas particulares

  • Imperial Hotel

  • Melia Santiago De Cuba

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