Islands and sea, sea and islands – the Caribbean region was made for cruising. Sailing between islands on a beautiful schooner or cruising around Cuba on a luxury motor yacht has got relaxation written all over it, but sailing and cruising in the Caribbean offers more than just idyllic swimming and sunsets off the starboard prow. Small ship cruises are a great way to see more of the region, soak up some culture and sample some sailing or diving, too, all while traveling responsibly.

Where are we cruising to?

The Bahamas is a great cruising destination. It could have been designed by a sailing fanatic, with hundreds of compact and colossally gorgeous cays and islands scattered through turquoise waters that you can easily scoot between when the wind’s in your sails. The Bahamas isn’t technically in the Caribbean, but it is the gateway to the region and you really won’t care about trifling details like that once you’re on deck, swooshing towards an idyllic sandy bay for an afternoon’s snorkelling.
Cuba is another superb destination for a small ship cruise or sailing vacation. A looping route that takes you west from Havana on the north coast, all the way round to Trinidad and Cienfuegos on the south coast, fills a wonderful week. You can enjoy the Canarreos Archipelago – a superb diving and snorkelling region – and there are lots of places to stop off along the way that will bring you up to speed with the culture, natural wonders and current conditions in Cuba.

What are we cruising on?

A range of small, environmentally responsible vessels ply the waters of the Caribbean. You can join a small ship cruise around Cuba, on a motor yacht with space for 72 passengers, or a beautiful three masted sailing cruiser, with 64 passengers, which uses a combination of wind and motor power. Or go micro and hop aboard a small yacht that takes just six guests for a week’s voyage that combines diving and snorkelling with historical tours.
In the Bahamas, embrace the romance of the sea big time by boarding a replica historic windjammer – a vision of billowing sails and polished brass – that takes up to 24 guests. On a ship this size you can always find a quiet spot to relax with a book, but anyone with nautical leanings is welcome to help the crew sail the ship, raising sails or taking a turn at the helm.
Larger boats come with larger crews and a bigger choice of cabins, while a small yacht that takes six passengers will have a crew of just two or three, including a captain and cook. Small yachts offer the ‘purest’ nautical experience, relying on the natural power of the wind to travel and only using the motor to navigate into harbour or when conditions are very still. All vessels will have well established environmental policies, though, from waste disposal (larger vessels often have an on board waste treatment system to reduce pollution) to shopping for provisions locally.
Whatever cruise and vessel you choose, small is beautiful. Huge cruise ships chug their way around the Caribbean, but we never recommend boarding one of these polluting behemoths. Read more about our stance on giant cruise ships. Small ships and yachts are the responsible alternative. They minimise pollution, and also negative social and environmental impacts. A small group of passengers, rather than a whole cruise liner’s worth, can visit smaller communities without swamping them or putting strain on local amenities. In addition, by visiting many different locations, small cruise ships support those places that don’t usually benefit from large scale cruises and spread the financial benefits of tourism far and wide.
Small cruise ships and sailing yachts are not only the responsible choice, they are also the more enjoyable one. A small vessel can sail you into the remote bays and quiet ports that bigger cruise ships can’t access. It takes you to hidden corners, cays and communities, arriving quietly, enjoying a warm welcome and leaving no trace.
Travel Team
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Things to do on a small ship cruise in the Caribbean

Some small ship cruises have a set itinerary, others are prepared to be blown by the wind – literally – but all cruise vacations will have a ‘theme’. Sailing around the Bahamas is usually about enjoying great snorkelling, quiet beaches, gentle hiking on remote islands and the odd sundowner in a stylish yacht club.
Small ship cruising around Cuba, on the other hand, typically involves more conventional sightseeing, with daily onshore visits that get you closer to the culture, history, music and people of this fascinating island, rather than sailing you straight past it. You might hike through a national park with a local naturalist guide, or take a city tour of Havana or Trinidad, visiting local artists, schools and museums before returning to the ship each night.
Cuba is also a great destination for diving and snorkelling, with the 350 islets that make up the Canarreos Archipelago home to healthy and intact coral reefs. Compared to the rest of the Caribbean, Cuba’s coral reef ecosystems are thriving, thanks to far less coastal development and strong environmental laws and policies. You can enjoy this marine magnificence by joining a live-aboard boat that carries diving equipment, either included in the cost or available to rent. It will sail between reefs and dive spots, as well as exploring key sights and cities on the Cuban mainland.

Small ship cruising nitty gritty

Unless you charter a yacht privately – and you can do this easily in Cuba and the British Virgin Islands – you will be sharing your cruise with other passengers; how many depends on the size of the vessel. A yacht may have room for just six passengers in total, with cabins that are compact and designed purely for sleeping in, whereas a small cruise ship may have 50 to 100 passengers with a range of cabin sizes and styles.
In the Caribbean, the cruise season runs from November to May, when the weather is at its sunniest and driest and there’s no risk of hurricanes. Cruises depart on set dates and usually last for a week, with itineraries that range from fixed to fully flexible. Charter the yacht yourself and you can decide on all these details – departure date, duration and destinations. Caribbean small ship cruises are often run on an all inclusive basis, with all meals cooked on board.
Written by Joanna Simmons
Photo credits: [Page banner: Seann McAuliffe] [Small ship cruising: _dChris] [Small crew yacht: Lisa Bat] [Cuba diving: Patty Ho]