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 - 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...

14 Night - Discover Eastern Caribbean & Grenadines
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, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Prickly Pear Cays, Anguilla / Marigot, Saint Martin, Marigot, Saint Martin
2026 Sails: Nov 29, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot, St Martin, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

10 Night - The Americas & Caribbean
Starting in Fort Lauderdale, Road Town, Gustavia, St Barthelemy, Pointe-a-Pitre, French West Indies, Kingstown, Castries, St Lucia, Fort-de-France, St Kitts (Basseterre), San Juan
2026 Sails: Dec 3, More...

17 Night - The Americas & Caribbean
Starting in Fort Lauderdale, Road Town, Gustavia, St Barthelemy, Pointe-a-Pitre, French West Indies, Kingstown, Castries, St Lucia, Fort-de-France, St Kitts (Basseterre), San Juan, Jost Van Dyke, British Virgin Islands, Marigot, St Martin, St Johns, St Thomas, Fort Lauderdale
2026 Sails: Dec 3, More...

16 Night - Star Collector : Windward Islands & Spanish New World
Starting in Bridgetown, Rodney Bay, The Pitons, Scarborough, Tobago, Bequia, Mayreau, St Georges, Willemstad AN, Oranjestad, Cartagena CO, Bocas del Toro, San Blas, Panama, Panama Canal, Balboa / Fuerte Amador
2026 Sails: Dec 4, More...

8 Night - Windward Ways & Tobago Cays
Starting in Bridgetown, Rodney Bay, The Pitons, Scarborough, Tobago, Bequia, Mayreau, St Georges, Willemstad AN, Oranjestad
2026 Sails: Dec 4, More...

13 Night - Caribbean Combination Cruise : San Juan, Antigua & St. Lucia
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, San Juan
2026 Sails: Dec 5, More...