Cuba Yacht Charter Guide

For decades Cuba has been a magnet for Western holidaymakers. That’s despite Cold War tensions and trade embargoes - little more than a media distraction from all that Cuba has to offer the visitor. If you can get there, it’s a great place to visit, a top destination to be enjoyed before it all changes. Havana is a fascinating city, and the sailing out of Cienfuegos has to be experienced to be believed.

About Yacht Charters in Cuba

Typically, a Cuban bareboat charter itinerary will take you either southeast or southwest of the base at Cienfuegos. To cover the whole sailing region will require an extended charter, and even on a short holiday there are some relatively long day passages involved. But the sailing conditions are good and it's worth it. And if the sailing itself is your passion, that's perfect!

Jardines de la Reina

A south-easterly course has the distinct advantage of a stopover in Trinidad. After all, if you are travelling to Cuba you want to do more than just soak up the fantastic tropical sun with life at sea. Trinidad is at the heart of European conquest of the Americas, so rich in history that it is a UNESCO World Heritage site. Stop awhile and take in the undoubted attractions.

Putting the Cuban mainland astern, it's a short distance to Cayo Blanco de Casilda, suitable for an overnight stay. Next day it's a full day's crossing to the archipelago Christopher Columbus called Jardines de la Reina (Gardens of the Queen). Popular anchorages in this area include Cayo Bréton, Cayo Caballones and Cayo Cuervo, all beautiful spots from which to snorkel and swim, and otherwise enjoy the tranquility of these peaceful waters.

Archipiélago de los Canarreos

The alternative sailing itinerary out of Cienfuegos is exclusively a tropical island exploration to the southwest. First-up is Cayo Guano del este, where you can anchor close to the distinctive lighthouse. From there a series of relatively short island hops will take you westward as far as Cayo Canal Rica. Along the way Cayo Largo del Sur is developed for tourism with a modern marina and several resorts. Playa Sirena is one of Cuba's most popular beach attractions.

Other places of interest in the Canarreos Archipelago include Quinto Canal, Cayo Rosario and Cayo Estopa – all brilliant destinations on a Cuban bareboat charter.

Sailing Conditions off Cuba's Southern Coast

Cuba's southern coast is the more sheltered side of the country. In Cuban waters you will experience typical Caribbean weather, with little variation between seasons. January is the coolest month (but still very comfortable for sailing) and August the hottest.

As throughout the region, the possibility of hurricanes peaks in late summer. During normal weather conditions the wind, which prevails from the east and north-east, is generally calm to moderate, but can become fresh, particularly during the cooler months.

Cuba remains an authoritarian state and there are some restrictions and regulations not imposed in other popular sailing destinations. Talk to us about the formalities, and let us assure you they will in no way hinder your enjoyment of a bareboat sailing holiday in Cuba.

Getting to Cuba for a sailing holiday requires arrival into Havana, which has daily flights from Europe, Canada, Mexico and other Caribbean islands. Our charter partners provide transfers from Havana to Cienfuegos, and all the in-country support you may require.

Enquire Now - Click Here   or view our bareboats and crewed yachts.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

  • Matching any competitive offer 
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience

We will match any discount website offer on charter boat price, and still provide our customary high level of service. We do more than just book yachts!

Read our free charter guide for all you need to know about planning your sailing holiday.

Yachts in Cuba

Bali 4.5 Open Space
Bali 4.5 Open Space - 44.6' (13.6m) 8 Guests
Lagoon 42
Lagoon 42 - 42' (12.8m) 8 Guests
Catana 50
Catana 50 - 52.5' (16m) 10 Guests
Bavaria 49
Bavaria 49 - 49' (14.9m) 10 Guests
Bavaria Cruiser 46
Bavaria Cruiser 46 - 47' (14.3m) 8 Guests

Enquire about Cuba

For a personalized proposal with all suitable options please complete...
required fields