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: Jan 3, Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Jan 4, Jan 18, More...

7 Night - Philipsburg to Philipsburg
Starting in Philipsburg, St Maarten, St Johns, St Thomas, Little Bay, Montserrat, Castries, St Lucia, Bequia, Les Saintes, Philipsburg, St Maarten
2026 Sails: Jan 4, Jan 11, Feb 19, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Terre-De-Haut, Iles Des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, More...

8 Night - A Tall Ship's Dream Destination
Starting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Jan 11, Nov 29, More...

7 Night - Lush & Lovely Islands of the Lesser Antilles
Starting in Philipsburg, St Maarten, Basseterre, Gustavia, St Johns, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Jan 11, More...

10 Night - Blue Waters of the Leeward Islands
Starting in Philipsburg, St Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 14, More...

17 Night - Star Collector : Hidden Gems of the Caribbean
Starting in Philipsburg, St Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 14, More...

7 Night - Yachtsman's Caribbean
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
2026 Sails: Jan 17, Jan 31, Mar 7, Mar 28, More...

7 Night - Philipsburg to Bridgetown
Starting in Philipsburg, St Maarten, St John VI, Gustavia, St Barthelemy, Roseau, St Georges, Trois Ilets, Kingstown, St Vincent, Bridgetown
2026 Sails: Jan 18, Feb 26, More...