The Islands

The Caribbean chain of islands can be split into the Windward and Leeward Islands. South of Dominica are the Windwards which embrace the warm easterly trade winds. They are more mountainous and vary greatly in size. Both trips will transit through and visit the Windward Islands visiting idyllic archipelagos such as Tobago Cays.

The Leeward islands round away from the Atlantic to the northwest. Some of these islands are mountainous like the Windward Islands however many are flatter and there are many beaches to enjoy. Antigua, a Caribbean hub of yachting and a destination on the latter trip, is included in the Leeward Islands.

Which Islands you visit on your trip will depend precisely on weather an timings but you can expect to visit a new island almost every day! 

See our availability and prices

The Yacht

The Yacht is a Challenger 72, built to sail around the world. A feat it has achieved twice in the BT Global Challenge Race. She is a very safe and solid yacht, spacious and comfy; well suited to sailing in the Caribbean. She meets all MCA (Maritime and Coastguard Agency) safety Category 0 (the highest level) Coding requirements.

There will be a professional skipper and mate aboard who will ensure your safety, give as much instruction/training/coaching as needed to enable the crew all come together to sail the boat as a team and for you to achieve your goals. You will take an active role in helping sail and run the boat.

The accommodation is arranged towards the stern of the boat in 2 areas comfy bunks. There is good refrigeration on board and a water maker so plenty of showers will be available.

Prices & Travel

Prices

• 7 Day Trip: £1749 - 16-22 December 2026
• 10 Day Trip: £2499 - 3-12 January 2027

Included within the price...

• All food on board
• Mooring fees
• Custom entry fees
• Insurance
• Foul weather gear (if needed! - unlikely)

Not included

• Travel to and from the yacht

7 Day Itinerary: St Lucia to Grenada

Following on for a First Class Atlantic Crossing the yacht will have a rest in St Lucia before departing on a fantastic trip, south, through the Windward Islands to Grenada.

Day 1: Join the Yacht in the morning to meet your fellow Caribbean adventurous, familiarise with the vessel and set out on a short training sail/passage. Perhaps spend the first night anchored under the Pitons.

Day 2-5: Depart St Lucia and head into St Vincent & the Grenadines. This incredible stretch of the Caribbean has over 10 different islands to choose from. Work your way gently through some of them experiencing nature at its fullest. Carriacou, Union, Tabago Cays, Canouan, Mustique, Bequia & St Vincent are all options for this part of the trip.

Day 6: Depart St Vincent & the Grenadines to head for Grenada for your final port of call. Enjoy your final meal either at anchor under the setting Carribean sun or at a local beach bar

Day 7: Sort outs and farewells. You will be able to depart the Yacht from early afternoon in time to make it home for Christmas or to further extend your Caribbean holiday in Grenada.

*This is an example itinerary based on the expected seasonal weather. Actual destination or timings may vary.

See our availability and prices

10 Day Itinerary: Grenada - Antigua

Start your new year off with some sailing in the Caribbean peak season. Stable winds, warm temperatures and plenty to explore.

Day 1: Join the Yacht in the morning to meet your fellow Caribbean adventurous, familiarise with the vessel and set out on a short training sail/passage. Perhaps spend the first night anchored under the Caribbean starts ready to push off into St Vincent and the Grenadines. Carriacou, Union, Tabago Cays, Canouan, Mustique, Bequia & St Vincent are all options for this part of the trip.

Day 2 - 5: Set of from Grenada to explore St Vincent & the Grenadines. This incredible stretch of the Caribbean has over 10 different islands to choose from. Work your way gently through some of them experiencing nature at its fullest.

Day 6 - 9: Depart the Grenadines and begin your trip up to Antigua and the leeward Islands. Martinique, Dominica, Ils des Saints, Guadeloupe and Monserrat are all options for this segment of the cruise. The passages will be a little longer but there will still be plenty of opportunity to visit a few islands on route, get ashore and explore. Arrive in Antigua in the afternoon or evening of day 9 ready to enjoy a final evening meal at anchor or at a local restaurant.

Day 10: Sort outs and farewells. You will be able to depart the Yacht from early afternoon in time to fly that afternoon, extend your Caribbean holiday in Antigua or perhaps even have a couple of quiet days before joining the trip back to the UK!

*This is an example itinerary based on the expected seasonal weather. Actual destination or timings may vary.

See our availability and prices

Looking for a Skippered Caribbean Sailing Holiday?

If you're looking for a skippered sailing holiday in the Caribbean, there's another option besides chartering an entire yacht.

Join our professionally skippered Challenger 72 and sail between Caribbean islands as part of a crew of like-minded people. With an experienced skipper and mate aboard, you can enjoy the sailing without taking responsibility for running the yacht yourself.

Unlike a traditional skippered charter, there's no need to organise a whole boat. Simply book an individual berth, join on your own, as a couple or with a friend, and become part of the crew.

These are hands-on sailing holidays, so you'll be encouraged to get involved in helming, sail handling and navigation, while still having time to enjoy the islands.

More About Sailing in the Caribbean

Thinking about joining one of our Caribbean sailing holidays? We've put together a collection of articles to help you discover what to expect, understand the sailing conditions and decide whether this type of holiday is right for you.

Whether you're wondering what life aboard is like, considering joining on your own or simply dreaming of escaping the British winter, these guides should help.

• Why a Caribbean Sailing Holiday Beats a Beach Resort in Winter – Discover why exploring the islands under sail offers a very different experience from a traditional resort holiday.
• What It's Really Like on a Caribbean Sailing Holiday – From sailing between islands to life aboard and time ashore, find out what to expect.
• Is a Caribbean Sailing Holiday Right for You? – Explore the experience, sailing involvement and practical considerations before booking.
• Winter Sailing in the Caribbean: Trade Winds, Weather and Conditions Explained – Learn about the trade winds, temperatures and sailing conditions that make the Caribbean such a popular winter destination.
• From UK Winter to Caribbean Trade Winds: Why Sailors Escape South – Discover the appeal of exchanging short winter days for sunshine and Caribbean sailing.
• Types of Caribbean Sailing Holidays: Charter vs Hands-On Crew Trips – Understand the differences between chartering a yacht and booking an individual berth aboard a professionally skippered yacht.
• Caribbean Sailing Holidays for Solo Travellers: Can You Join a Yacht on Your Own? – Find out how joining individually works, from meeting the crew to accommodation and life aboard.