7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan
2026 Sails: Nov 8, Nov 22, 2027: Nov 8, Nov 22, 2028: Mar 13, Mar 27, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan, Cruz Bay, St John VI, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 8, 2027: Nov 8, 2028: Mar 13, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, Cruz Bay, St John VI, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan
2026 Sails: Nov 15, 2027: Nov 1, Nov 15, 2028: Mar 20, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 22, 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...

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

7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan
2026 Sails: Dec 6, Dec 20, 2027: Jan 3, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Dec 6, Dec 20, 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 (Am), Soufriere, St Lucia (Pm), Bridgetown, Barbados
2026 Sails: Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan, Cruz Bay, St John VI, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2027 Sails: Jan 3, More...