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Unforgettable Caribbean Sailing Charters

We offer unique, personalized, and boutique sailing charter experiences throughout the Windward Islands of the Caribbean, from St. Lucia down to the Grenadines and Grenada, which are some of the most beautiful, untouched, and pristine parts of the Caribbean. The Grenadines are called the “jewel of the Caribbean” for a reason, with sparkling waters, hundreds of islands (many uninhabited), and comfortable, enjoying sailing yachts.

Each package below offers a different destination and length of charter, whether you’re looking for just a couple says around a certain island, or a week-long cruise through the Grenadines. Each charter package has a selection of yachts, catamarans, and crews.

3 Incredible Destinations

Set sail to St. Lucia, Martinique, or the beautiful Grenadines & Grenada.

Suggested Itineraries

Suggested itineraries for the best places to see, but still personalizable to you.

Proven Fleet of Yachts

We have a seasoned, well-maintained fleet of yachts, catamarans, and crews.

Always Skippered

Crewed/skippered for safety and comfort, so you can relax and enjoy the trip.

Caribbean Sailing Charters, by Destination

St. Lucia Sailing Charters

St. Lucia Charters

Experience the majestic island of St. Lucia the best way possible - from the sea. Set sail from Marigot Bay to visit some of the best spots in St. Lucia, including the Pitons Mountains.

2 Itineraries Available

Available Yachts/Catamarans:
Sun Odyssey 47 Monohull Yacht Beneteau Cyclades 50 Monohull Yacht Rob & Caine Catamaran Yacht
Sailing Charters to Martinique

Martinique Charters

Sail to Martinique and see for yourself the island's enchanting French-Caribbean culture with delectable cuisine, lovely beaches and snorkeling, and volcanic landscapes.

4 Itineraries Available

Available Yachts/Catamarans:
Sun Odyssey 47 Monohull Yacht Beneteau Cyclades 50 Monohull Yacht Rob & Caine Catamaran Yacht All Inclusive Silent Wing Yacht Charter
Sailing Charters to Grenadines and Grenada

Grenadines & Grenada Charters

Referred to as "the jewels of the Caribbean", the Grenadines are a series of hundreds of secluded, sandy islands, mostly uninhabited, and surrounded by sparkling Caribbean waters.

5 Itineraries Available

Available Yachts/Catamarans:
Sun Odyssey 47 Monohull Yacht Beneteau Cyclades 50 Monohull Yacht Rob & Caine Catamaran Yacht All Inclusive Silent Wing Yacht Charter All Inclusive Traditional Schooner
By Itinerary (Shortest to Longest)
St. Lucia Day Sail Tours
St. Lucia Day Sail - South
2-10 People
1 Day (No Overnight)

Sail from Marigot Bay down the west coast of St. Lucia to see the Pitons, Diamond Waterfall, Botanical Gardens, Active Volcano, and more. Stop to snorkel along the way and enjoy lunch and rum punch aboard.

Available as group or private, monohull or catamaran Read more.

St. Lucia Day Sail Tours
St. Lucia Day Sail - North
2-10 People
1 Day (No Overnight)

Sail from Marigot Bay up the west coast of St. Lucia to Rodney Bay and Reduit Beach where you can enjoy lunch ashore, some time at the beach, or a visit to the national park and old fort.

Available as group or private, monohull or catamaran. Read more.

St. Lucia Day Sail Tours
St. Lucia Sunset Cruise
2-10 People
1 Day (No Overnight)

Leaving at around 5pm, our sunset cruise departs from Marigot and takes you for a romantic sail by the calming evening wings. Enjoy complimentary sparkling wine and hors d'oeuvres while on board. Upgrade to make it a private cruise.

Available as group or private Read more.

St. Lucia Explorer Charter Itinerary
St. Lucia Explorer
2-10 People
2 Days/1 Night

Essentially our two day sails combined into a short, easy charter with one overnight. See the best spots on the island, including Rodney Bay to the north and the Pitons to the south.

Available yachts: catamaran Read more.

St. Lucia Explorer Voyager Itinerary
St. Lucia Voyager
2-10 People
3 Days/2 Nights

Sail from Marigot Bay up to Rodney Bay to explore the area. Next day, sail south, stop to snorkel at Anse Chastanet known for its amazing reefs. On the last day sail to Soufriere and the Pitons before sailing back.

Available yachts: monohulls or catamaran Read more.

Martinique Mariner
2-10 People
3 Days/2 Nights

Sail from St. Lucia to Martinique and discover some of the most popular and hidden treasures of Martinique, including Forte-de-France (the 'Paris of the Caribbean') as well as some beautiful little local fishing villages and quiet beaches.

Available yachts: monohulls or catamaran Read more.

Martinique Yachter Charter Itinerary
Martinique Yachter
2-10 People
4 Days/3 Nights

Similar to our Martinique Mariner Charter but with a bit more time to enjoy Martinique, such as a stunning black beach by the name of Anse Noire. There's plenty of exquisite restaurants and even a casino you can visit along this trip.

Available yacht: monohulls or catamaran Read more.

Grenadines 4 Islands Charter Itinerary
Grenadines 4 Islands
2-10 People
4 Days/3 Nights

As the name suggests, this short itinerary gives you a great taste of the Grenadines and four of its beautiful islands, including St. Vincent, Young Island Cut, Bequia, and of course, St. Lucia. A good choice if you'd like to split your vacation between land and sea.

Available yachts: monohulls or catamaran Read more.

Grenadines 7 Islands Plus Charter Itinerary
Grenadines 7 Islands Plus
2-10 People
5 Days/4 Nights

This charter gives you just enough time to sail and experience some of the truly authentic Grenadines islands like Mayreau, Young Islands Cut and the gorgeous Tobago Cays with its pristine protected reefs, uninhabited islands, and secluded beaches.

Available yacht: monohulls or catamaran Read more.

Martinique Jack Charter Itinerary
Martinique Jack
2-10 People
6 Days/5 Nights

A true sailing experience. Start with one night on the northern Rodney Bay of St. Lucia before heading to Martinique the next day. Then enjoy a lovely 5 days sailing and exploring Martinique, including the iconic Mt. Pelée sleeping volcano.

Available yachts: monohulls or catamaran Read more.

Grenadines Navigator Charter Itinerary
Grenadines Navigator
2-10 People
6 Days/5 Nights

Everything you need to see in the Grenadines - St. Vincent, Bequia, Palm Island, Tobago Cays, Union Island, and more. All the time you need to relax aboard and ashore; beautiful emerald waters, secluded beaches, pristine snorkeling, and so much more.

Available yachts: monohulls or catamaran Read more.

Martinique Yachter Charter Itinerary
Windward Islander
2-10 People
8 Days/7 Nights

Similar to our Martinique Mariner Charter but with a bit more time to enjoy Martinique, such as a stunning black beach by the name of Anse Noire. There's plenty of exquisite restaurants and even a casino you can visit along this trip.

Available yachts: monohulls or catamaran Read more.

Caribbean Fortune Hunter Charter Itinerary
Caribbean Fortune Hunter
2-10 People
8 Days/7 Nights

If you love the sea and want to explore two very unique incredibly beautiful Caribbean islands - being St. Lucia and Martinique, this combo charter is a wonderful option. You'll see the best spots of both islands that only the sea can bring you to.

Available yachts: monohulls or catamaran Read more.

One-Way Grenada Charter Itinerary
One-Way Grenada
2-10 People
8 Days/7 Nights

The itinerary that will give you the most sailing time in the Grenadines. Enjoy plenty of time cruising through the archipelago known as the jewels of the Caribbean before taking a flight back from Grenada to St. Lucia (saving you from sailing back).

Available yachts: monohulls or catamaran Read more.

All Inclusive Caribbean Charter Catamaran
All Inclusive Sailing Catamaran
2-6 People
Min 4 Days

We invite you to set sail on a unique and luxurious Caribbean sailing vacation aboard this spacious, stable, and airy catamaran. Deserted islands and beaches, unspoiled Caribbean settings, and a brilliant French chef will make your voyage unforgettable!

This charter is aboard a 46' catamaran for up to 6 people. Read more.

Yachts, Catamarans, & Crews

When you make an inquiry or a booking for a sailing charter, you can choose which type of yacht you would prefer, whether it be a monohull, catamaran, or our all-inclusive option; 'Silent Wing'. Some yachts have specific crew & captains while others can change depending on scheduling and whereabouts of the charters.

Catalina Day Sail Yacht

Catalina 42

A mono hull yacht used for our day-sail tours and sunset cruises in St. Lucia, based in Marigot Bay.

Beneteau Cyclades 50 Yacht

Beneteau Cyclades 50

A stylish modern yacht and with plenty of space at 50' long. Can accommodate up to 6 guests plus crew.

Rob & Caine Catamaran Yacht

Rob & Caine Catamaran

Large, beautiful, spacious catamaran. Can accommodate up to 10 guests but sleeps 6 most comfortably.

All Inclusive Catamaran

All-inclusive Catamaran

An all-inclusive, spacious and enchanting catamaran with crew members, Bea and Vito.

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