Offshore Sailing in the Caribbean

This is a sample itinerary only showing some of the possible options for the route from Antigua to Jamaica. The wind and weather at the time will shape what we can actually do and when so these are sample highlights.

Where are Antigua and Jamaica?

Antigua is an island located in the Eastern Caribbean, in the northern sector of the Leeward Islands in the Lesser Antilles. It’s known for its rich history, vibrant culture, and numerous stunning beaches. Jamaica lies around 90 miles south of Cuba.

Join the yacht, sailing and training in Antigua

Crew members join the boat in Falmouth Harbour, Antigua. This is one of the Windward Islands in the Lesser Antilles and is full of maritime history. Its corrugated coasts have hundreds of little coves lapped by the turquoise water, while the sheltered bays have provided refuge for everyone from Admiral Nelson to buccaneers and modern-day sailors.

There will be a real sense of excitement for the voyage to come as we help everyone get their belongings packed away and ready to start the sailing lifestyle. After safety briefings and lunch, we’ll slip lines and head out onto the water to learn new skills, revise any existing ones, and get up to speed for the sailing to come. We will practice tacking, gybing, rescuing a casualty who has fallen overboard, and all the other skills we’ll need.  We’ll likely be in this area for a couple nights.

Antigua to St Kitts, Nevis & Saba

The sail from Antigua to St Kitts and Nevis is a fast downwind charge and will make sure we are ready for the offshore passage to come. Saint Kitts and Nevis is a gorgeous Caribbean destination to visit, and hopefully we have time to explore. It is an island of rainforests, Mount Liamuiga volcano, and pristine sandy beaches. Its capital, Basseterre, is full of well-preserved colonial architecture and historic landmarks like Brimstone Hill Fortress National Park. We will explore these islands for a few days until it’s time to set off for Jamaica!

Offshore passage to Jamaica

Our major offshore passage is a fast and exhilarating sail that, with the powerful trade winds pushing us along, should take around 4-5 days and nights at sea. Our first task is to navigate our way south of the British Virgin Islands. Depending on the wind angle, this first section can have more challenging conditions, but then we turn west for a fast and utterly exhilarating downwind sail past the south coasts of Puerto Rico, the Dominican Republic and Haiti. Cuba lies ahead, so we turn south and make landfall on the north coast of Jamaica.

Note: these are true sailing adventures!

These are true sailing adventures that require more than just a presence on board—they demand enthusiasm, teamwork, and a positive spirit from each crew member. To fully embrace and benefit from these experiences, it’s crucial that crew come prepared to contribute actively to the life and tasks on the vessel. Those who step up with the right attitude will find that the rewards are immense. Not only will you gain new skills and face exhilarating challenges, but you’ll also forge deep connections with fellow adventurers and create memories that last a lifetime.