The Most Beautiful Towns To Visit While Sailing in Cuba

Cuba is home to some truly incredible towns to explore during your next sailing trip around the Caribbean and beyond
Cuba is home to some truly incredible towns to explore during your next sailing trip around the Caribbean and beyond | © Ian Dagnall / Alamy Stock Photo
Photo of Nick Dauk
2 November 2021

Few islands on the planet are as complex and captivating as Cuba. Just 90mi (145km) from the United States – yet a world away in nearly every sense – the Pearl of the Antilles is so much more than cars, cigars and crumbling snapshots of Havana. Beyond the sea of pink Cadillacs are coastal towns that feel as old-world as you’d imagine. Whether you’re a fan of rum, seafood, or simply a good fishing hole, you’ll find everything when sailing the towns of Cuba’s coast.

Chart a course for Cuba by renting a yacht with SamBoat.


Architectural Landmark
The coastline of Playa Bani in Guardalavaca, Cuba
© Robert Harding / Alamy Stock Photo
Your snorkel and fishing rod will get their fair share of use off the coast of Guardalavaca. Wading around the northern coast of Cuba, the deep waters and coral reefs offshore make Guardalavaca an ideal port of call for fishing and diving. Need to sit on land for a moment and let it be? Take a seat next to a bronze Beatle on a bench at John Lennon Park and watch the waves crash on Playa Bani.


Natural Feature
The walkway down to Varadero Beach in Varadero, Cuba
© Robert Harding / Alamy Stock Photo
Matanzas is a popular haven for poetry, Afro-Cuban folklore and other cultural introductions to Cuba’s diverse population – but we think you should set sail due east to the nearby Hicacos Peninsula. Home to 20km (12.4mi) of coastline and all-inclusive hotels, you may just want to treat yourself to a luxe night on land. Varadero Golf Club is a pretty picturesque place to play 18 holes, though you can still get a solid afternoon of exercise by walking the trails of Reserva Ecológica Varahicacos to the historic Ambrosio burial caves.

Playa Ancon

Natural Feature
A row of umbrellas on the beach of Playa Ancon near Trinidad, Cuba, Caribbean
© Peter Schickert / Alamy Stock Photo
Though the colonial city of Trinidad is only 10km (6.2mi) away, the Playa Ancon peninsula feels surprisingly untouched. Only a few resorts dot the long stretches of sandy beach, with just enough restaurants covering the space between to offer the right amount of options. There’s not much to do here – and that’s the point. You deserve a day with no worries other than keeping your toes dug into the sand and keeping the Cuba Libres coming.


Architectural Landmark
Baracoa Street with a row of colonial buildings in Cuba
© Andrew Paul Travel / Alamy Stock Photo
The island had been inhabited for thousands of years before Christopher Columbus arrived – but history buffs who want to gain a sense of Cuba’s colonial history should drop anchor at Baracoa. Known as the “First City of Cuba”, you can cover this town by hopscotching through its landmarks. The Museo Municipal features special exhibits like the remains of Cuba’s aboriginal people – while the Cruz de la Parra sites mark Columbus’ arrival.

Santiago de Cuba

Architectural Landmark
The ancient Cathedral Nuestra Senora de la Asuncion in Santiago de Cuba, Cuba
© Michel and Gabrielle Therin-Weise / Alamy Stock Photo
Santiago de Cuba has a little something for everyone who steps off your boat – and hiking the steep mountains of Parque Nacional Turquino will earn you a well-deserved drink at the Bacardi Rum Factory. Your toes can get a workout without venturing far from the lively Céspedes Park if you dance your way through the clubs like Casa de las Tradiciones. Feel like you could stay on your feet all day and all night? Make your visit to Santiago de Cuba during carnival time – around the end of July – and party around the clock.


Architectural Landmark
A classic 1950's Plymouth taxi, locally known as Almendrones in the town of Cienfuegos, Cuba, Caribbean
© Robert Harding / Alamy Stock Photo
Leave the waves behind for the calm waters of the Bay of Cienfuegos. The Museo Historico Naval Nacional is far from the only example of Cienfuegos grand architecture in the city – but this beautiful blue building should be your first stop in this nautical Unesco World Heritage Site. When you’re not strolling the Malecón staring agape at Punta Gorda’s eccentric palaces, stock up on local coffee, tobacco and sugar cane to keep you content at sea.

Nueva Gerona

Architectural Landmark

Close to Cayo Largo del Sur – one of the ports where your yacht can gain official passage throughout Cuba – Nueva Gerona is the sole city on Isla de la Juventud, otherwise known as the “Island of Youth”. Fishing and swimming on the black sands of Playa Los Estudiantes and Bibijagua may seem like paradise, but an exploration of Nueva Gerona’s interior will lead you to the Presidio Modelo – an abandoned prison where Fidel Castro served time.


Architectural Landmark
A row of vintage classic American taxis waiting for tourists in Havana, Cuba
© Jim Monk / Alamy Stock Photo
Is it any surprise that Havana has made the list? Cruising in classic cars, drinking Cuba Libre cocktails in the Plaza Vieja and watching sunsets from the Malecón coastal esplanade are just a few of the reasons you’ll fall in love with this city. But the main reason? The people. We can’t urge you enough to venture away from the main square and into the local neighborhoods to eat Cuba’s national dish of ropa vieja at family-run paladares – tiny restaurants, often in people’s homes. If you’re not due back at port for a few hours, hire a driver, hop in a bright pink Cadillac and explore the caves, cigar fincas and painted mountains around Viñales.

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