Upcoming Passages. - 2026 is now completely full. Dates Available -2027 in the Caribbean
Grenada to
St Vincent in the Grenadines
Caribbean Sailing Adventure
From 12 January – February 3rd 2027
Join us aboard Osprey for a relaxed Caribbean sailing adventure from Grenada through the Grenadines to St Vincent.
Minimum stay: 10 days.
Explore beautiful islands, secluded anchorages, turquoise bays and lively Caribbean villages. Enjoy a mixture of day sailing and longer passages, with plenty of time for swimming, snorkelling and exploring ashore.
Cabins are offered rather than individual berths. Prices are based on twin sharing and cabins cannot be split. Couples and friends are welcome, experience is not essential but welcome.
Due to the difficulties of provisioning in some Caribbean islands, and our experience in crew preferring not to share with strangers Cabins are now offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Onboard Contribution
The daily onboard contribution is US$180 per person per day, based on twin-share accommodation, and includes food and fuel.
Marina and harbour fees are additional and are shared equally amongst the crew and settled at the end of your stay.
BYO alcohol.
The itinerary is flexible and will be adapted according to weather, sea conditions and routing decisions.
Come for 7-10 days or stay longer and experience the beautiful Windward Islands at a relaxed sailing pace.
2 Cabins Available
St Vincent, St Lutia to Martinique
Caribbean Sailing Adventure
4 – 18 February 2027
Join us aboard Osprey as we sail north from St Vincent through the lush volcanic islands of the Windward Islands, making our way to St Lucia and Martinique.
Minimum stay: 10 days.
This is a region of steep green mountains, rainforest-covered valleys, palm-fringed bays and colourful fishing villages. Sail between islands on the steady Caribbean trade winds, drop anchor beneath dramatic volcanic peaks and explore ashore when the mood takes you.
We’ll visit St Vincent, St Lucia and Martinique, with the possibility of stopping at smaller islands and secluded bays along the way. Expect a mix of relaxed coastal sailing and longer passages, warm-water swimming, snorkelling, local food and the distinctive blend of Caribbean and French culture found further north.
Due to the difficulties of provisioning in some Caribbean islands, and our experience in crew preferring not to share with strangers Cabins are now offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Onboard Contribution
The daily onboard contribution is US$180 per person per day, based on twin-share accommodation, and includes food and fuel.
Marina and harbour fees are additional and are shared equally amongst the crew and settled at the end of your stay.
BYO alcohol.
The itinerary is flexible and will be adapted according to weather, sea conditions and routing decisions.
Come for 7-10 days or stay longer and experience the beautiful Windward Islands at a relaxed sailing pace.
2 Cabins Available
Martinique to Guadeloupe
Caribbean Sailing Adventure
19 February – 5 March 2027
Join us aboard Osprey as we continue north from Martinique to Guadeloupe, exploring the beautiful islands of the French Caribbean along the way.
Minimum stay: 10 days.
This leg takes us through some of the most varied and characterful islands of the Lesser Antilles. Sail with the trade winds between lush volcanic coastlines, sheltered bays and colourful waterfront villages, while allowing plenty of time to get ashore and discover what makes each island unique.
In Martinique, enjoy the French-Caribbean atmosphere, explore colourful markets and historic towns, sample local rum and Creole cuisine, or head inland into the lush volcanic landscape.
As we sail north, we’ll have opportunities to discover islands such as Dominica, known for its spectacular rainforest, waterfalls, hot springs and rugged natural beauty. Time ashore might include exploring local villages, hiking through the rainforest or simply enjoying the island’s relaxed atmosphere.
We’ll then continue towards Guadeloupe, where French-Caribbean culture meets dramatic tropical landscapes. Explore the lively markets and waterfronts, visit waterfalls and rainforest on Basse-Terre, or enjoy the beaches and smaller islands around Grande-Terre.
The exact route will depend on weather and sailing conditions, with the flexibility to spend more time in the places that capture the crew’s imagination.
Due to the difficulties of provisioning in some Caribbean islands, and our experience in crew preferring not to share with strangers Cabins are now offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Cabins are offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Onboard Contribution
The daily onboard contribution is US$180 per person per day, based on twin-share accommodation, and includes food and fuel.
Marina and harbour fees are additional and are shared equally amongst the crew and settled at the end of your stay.
BYO alcohol.
The itinerary is flexible and will be adapted according to weather, sea conditions and routing decisions.
Come for 7-10 days or stay longer and discover the islands, culture and natural beauty of the French Caribbean at a relaxed sailing pace.
2 Cabins Available
Guadeloupe to Antigua
Caribbean Sailing Adventure
6 – 20 March 2027
Join us aboard Osprey as we sail north from Guadeloupe to Antigua, exploring the beautiful Leeward Islands along the way.
Minimum stay: 10 days.
Leaving Guadeloupe, we’ll follow the trade winds north through a chain of lush volcanic islands, quiet anchorages and colourful Caribbean communities.
There will be plenty of opportunities to get ashore and explore. Discover the rainforest, waterfalls and Creole culture of Guadeloupe, before continuing north towards islands such as Montserrat, where volcanic landscapes and the remains of the former capital tell a fascinating story.
As we approach Antigua, the scenery changes to sheltered bays, white-sand beaches and a rich maritime history. Explore historic Nelson’s Dockyard, wander through English Harbour, visit local markets or simply enjoy the island’s many beautiful anchorages.
We’ll combine relaxed island sailing with longer passages, with time for swimming, snorkelling, exploring ashore and enjoying the warmth and hospitality of the Caribbean.
Cabins are offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Due to the difficulties of provisioning in some Caribbean islands, and our experience in crew preferring not to share with strangers Cabins are now offered rather than individual berths. Prices are based on twin sharing. Couples and friends are welcome. Experience is not essential but is always welcome.
Onboard Contribution
The daily onboard contribution is US$180 per person per day, based on twin-share accommodation, and includes food and fuel.
Marina and harbour fees are additional and are shared equally amongst the crew and settled at the end of your stay.
BYO alcohol.
The itinerary is flexible and will be adapted according to weather, sea conditions and routing decisions.
Come for 7- 10 days or stay longer and discover the Leeward Islands at a relaxed sailing pace.
2 Cabins Available
More Sailing Dates Coming Soon.
Our Caribbean adventure doesn’t end in Antigua.
More dates and sailing opportunities will be added here soon as we continue north towards Annapolis and the Chesapeake Bay, where Osprey will spend the cyclone season.
Along the way, we’ll be offering a mixture of coastal cruising, offshore passages and island adventures, including time exploring the Bahamas and the waters of the western Atlantic.
There will be opportunities to join Osprey for longer passages, shorter cruising legs or simply to experience life aboard as we make our way north.
Watch this space — more routes, dates and availability coming soon.