8 Night - Sun, Sea, and Serenity
Starting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Deshaies, Basseterre, Gustavia, Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 28, More...

7 Night - Classic Caribbean
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Deshaies, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 28, More...

11 Night - A VIP Sailing Event
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Saint-Pierre, The Bight Bay / Norman Island, North Sound / Virgin Gorda, Gustavia, Philipsburg
2026 Sails: Mar 6, More...

14 Night - Yachtsman's Island Jewels
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Saint Pierre, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Pointe-a-Pitre, Guadeloupe, Trois Ilets, Martinique, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Mar 7, More...

7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 7, More...

7 Night - Cruise from St Maarten (Philipsburg) to St Thomas (Charlotte Amalie)
Starting in Philipsburg, Falmouth Bay, Charlestown, Nevis, Terre De Haut, Iles des Saintes, Saba, Gustavia, White Bay, Jost van Dyke, Charlotte Amalie, St Thomas
2026 Sails: Mar 8, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, 2027: Feb 13, Mar 13, More...

7 Night - James Beard Foundation : Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, More...

11 Night - Sailing On the Trade Winds
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Saint-Pierre, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Gustavia, Philipsburg
2026 Sails: Mar 16, More...