7 Night - Grenadines & Windwards Yachting
Starting in Bridgetown, Barbados, Speightstown, Barbados, Kingstown, Saint Vincent and the Grenadines, Bequia Island, Saint Vincent and the Grenadines, Mayreau Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados
2026 Sails: Jan 10, Feb 7, Mar 7, More...

7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Jan 10, Feb 14, Feb 28, Mar 21, Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, More...

7 Night - Windward Islands
Starting in Bridgetown, Barbados, Rodney Bay, St Lucia, Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
2026 Sails: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, More...

5 Night - Bridgetown / Bridgetown
Starting in Bridgetown, Bequia, St Georges, Canouan, Soufriere, Bridgetown
2026 Sails: Jan 11, More...

8 Night - Bridgetown / Aruba
Starting in Bridgetown, Les Anses-dArlet, Bequia, St Georges, Canouan, Kralendijk, Willemstad AN, Aruba
2026 Sails: Jan 16, More...

7 Night - Grenadine Islands
Starting in Bridgetown, Barbados, Captains Best, Grenadines, St Georges, Grenada, Tobago Cays, Grenadines, Kingstown, St Vincent (Morning), Admiralty Bay, Bequia (Pm), Fort-de-France, Martinique (Morning), Beach, Martinique (Afternoon), Marigot Bay, St Lucia (Morning), Soufriere, St Lucia (Afternoon), Bridgetown, Barbados
2026 Sails: Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, More...

14 Night - Star Collector : Captivating Caribbean
Starting in Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown, Bequia, Mayreau, Soufriere, Kralendijk, Willemstad AN, Oranjestad
2026 Sails: Jan 18, More...

7 Night - Jewels of the Windward Islands
Starting in Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown
2026 Sails: Jan 18, More...

14 Night - An Extended Journey Between Sophistication & Silky Sands
Starting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...

11 Night - the Best of the Secluded Caribbean Cruise
Starting in Bridgetown, Barbados, St Georges, Mayreau, Tobago Cays, Port Elizabeth VC, Bequia, Terre De Haut, Iles des Saintes, Charlestown, Nevis, South Friars Bay, Gustavia, Spanish Town, Virgin Gorda, Norman Island, St John VI (Cruz Bay), US Virgin Islands, San Juan
2026 Sails: Jan 20, More...