Sail in the Leeward Islands

Sail in the Leeward Islands of the Caribbean

Cruise, explore and sail in the beautiful Leeward Islands of the Caribbean on a hands on sailing holiday in January 2021.

The Leeward Islands are the northern chain of Islands in the Caribbean. Starting in Antigua you will sail to places like Dominica and Iles des Saintes, Guadeloupe, Barbuda, St Kitts and Nevis, Anguilla, St Martin and others.

Sail in the turquoise waters, anchor off pristine white sandy beaches. Swim or take the dinghy ashore.Sip cocktails in beach bars, eat freshly caught grilled tuna, wahoo, and dorado and breath in the exotic aromas of Caribbean spices.

The European heritage of the islands is everywhere.English, French, Dutch and local culture coupled with lush volcanic peaks tumbling down to palm lined beaches and sparkling waters create a lovely setting for a sailing adventure.

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The intention will be to do sail to a different island each day, maybe spend a couple of nights in one place, maybe do a night sail. There will be lots of sailing along with plenty of time to explore ashore.

The boat will be in Jolly Harbour in Antigua when you arrive and after settling in you will cast off. Antigua itself has 365 beaches, 1 for each day of the year.

Most of the Leeward Islands are volcanic, have undulating mountainous folds and are covered in lush tropical foliage. The odd island mass is flat and coral like Barbuda, a day sail from Antigua. The pink sands and miles of turquoise shoal water are wonderful. You may see sting rays, turtles and frigate birds.

With all these kinds of trips exactly where you go will depend on the weather along with swell from unusual directions, any new marine wildlife anchoring restrictions and customs clearance regulations. The skipper will be taking into account all of these factors but will keep you informed and discuss the options with you.

The Yacht is a 72ft Challenger Yacht. She sails beautifully and has sailed around the world twice.

She does require team work so it is hoped you would be keen to get stick in with everything on board. That said the skipper, mate and two watch leaders could sail the boat by themselves so if you wanted to just kick back and watch the pelicans plummet into the sea for fish and the world go by then you can!


Down below is a big light saloon and galley, navigation station, two heads with showers. There is good refrigeration on board and a water maker so plenty of showers will be available.

The accommodation is arranged towards the stern of the boat in areas of 2 and 5 comfy bunks.

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Stage payments are an option call 0203 006 3717 or email the office for details.

Starting and finishing in Antigua the dates are 2-16 January 2021

The price is £1495.

Included in the price is insurance and all food on board. If you would like to pay a deposit of £500 to secure your place use code CARIB4281 when checking out.

Flights are not included. Have a look here skyscanner.

If doing the first trip then generally, flights into Antigua would mean you would arrive at the yacht early evening.

You would need to depart the yacht in Antigua by 10am on 16th.

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Leeward Islands
2 - 16 January 2021
11 nights
Contact us
0203 006 3717
Our Locations

Shamrock Quay

William Street



SO14 5QL


c/o Cruising Association

CA House

1 Northey Street


E14 8BT

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