7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, Basseterre, St Kitts and Nevis, Roseau, Dominica, Castries, St Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Nov 28, Dec 19, 2027: Jan 30, Feb 13, Feb 27, Mar 27, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Nov 28, More...

7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 28, More...

7 Night - West Indies Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Soufriere Bay, Terre De Haut, Iles des Saintes, Philipsburg, Simpson Bay, Gustavia, St Johns AG
2026 Sails: Nov 28, More...

7 Night - Classic Yachtsman's
Starting in St Johns AG, Terre De Haut, Iles des Saintes, Cabrits, Dominica, Beach Stop, Martinique, St Georges, Grenada, Tobago Cays, Grenadines, Marigot Bay, St Lucia (Morning), Soufriere, St Lucia (Afternoon), Bridgetown, Barbados
2026 Sails: Nov 28, More...

7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Nov 28, Dec 12, 2027: Jan 9, More...

7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, Road Town, Tortola, British Virgin Islands, Basseterre, Saint Kitts and Nevis, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Nov 28, More...

7 Night - Grenadines & Windwards Yachting
Starting in Bridgetown, Barbados, Bridgetown / Port St Charles, Barbados, Kingstown / Bequia Island, Saint Vincent and the Grenadines, Bequia Island / Mayreau Island, Saint Vincent and the Grenadines, Mayreau Island / Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island / Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados
2026 Sails: Nov 29, Dec 27, 2027: Jan 23, Feb 20, Mar 20, More...

7 Night - A Journey Through a Caribbean Tapestry of Serenity & Splendour
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami
2026 Sails: Nov 29, More...

14 Night - An Extended Journey Through Golden Shores & Island Grace
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan
2026 Sails: Nov 29, More...