22 Night - Star Collector : Atlantic Interludes & Iberian Indulgences
Starting in Philipsburg, St Maarten, Ponta Delgada, Lisbon, Cadiz, Gibraltar, Malaga, Almeria, Spain, Cartagena ES, Palma De Mallorca, Barcelona
2026 Sails: Apr 4, More...

14 Night - Knot Your Average Crossing
Starting in Philipsburg, St Maarten, Ponta Delgada, Lisbon
2026 Sails: Apr 4, More...

14 Night - Cruise from St Maarten (Philipsburg) to Malaga
Starting in Philipsburg, Chrishi Beach, Nevis, Malaga
2026 Sails: Apr 18, More...

7 Night - St. Maarten to Barbados
Starting in Philipsburg, Gustavia, Carambola Beach, Pointe-a-Pitre, Cabrits (Portsmouth DM), Dominica, Fort-de-France, Port Elizabeth VC (Bequia), Bridgetown
2026 Sails: Oct 14, More...

7 Night - British & French Islands Discovery Cruise
Starting in Philipsburg, Sopers Hole, Tortola, Norman Island, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Gustavia, Terre De Haut, Iles des Saintes, Mayreau, Bridgetown, Barbados
2026 Sails: Nov 14, 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...

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: Nov 29, More...

7 Night - Yachtsman's Caribbean
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Dec 5, Dec 26, 2027: Jan 16, Jan 30, Feb 20, Mar 6, Mar 20, Dec 4, 2028: Jan 22, Feb 5, Feb 19, Mar 4, Mar 18, More...

14 Night - Yachtsman's Caribbean in Depth
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Terre-de-Haut, Iles des Saintes, Guadeloupe, Saint Pierre, Martinique, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 5, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Terre-De-Haut, Iles Des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Philipsburg, St Maarten
2026 Sails: Dec 5, More...