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...

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...

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, Dec 5, 2028: Jan 30, Feb 27, 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...

7 Night - History and Culture Visiting Caribbean Jewels
Starting in Philipsburg, Prickley Pear Cays, Gustavia, Charlestown, Nevis, Falmouth Bay, Barbuda, Les Saintes, Pointe-a-Pitre
2026 Sails: Mar 21, More...

20 Night - Eastbound Atlantic Ocean Crossing
Starting in Philipsburg, St Maarten, Ponta Delgada, Azores, Portugal, Malaga, Spain
2026 Sails: Mar 21, More...

34 Night - Eastbound Atlantic Ocean Crossing
Starting in Philipsburg, St Maarten, Ponta Delgada, Azores, Portugal, Malaga, Spain, Almeria, Spain, Cartagena ES, Ibiza / Balearic Islands, Spain, Mahon / Menorca / Balearic Islands, Spain, Cagliari / Sardinia, Italy, Gozo, Malta, Valletta, Malta, Syracuse, Sicily, Italy, Pilos, Greece, Monemvasia, Greece, Piraeus (Port of Athens), Greece
2026 Sails: Mar 21, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 21, More...