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 - 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...

11 Night - Jamaica to Antigua
Starting in Montego Bay, Jamaica, Port Antonio, Jamaica, Santo Domingo, Dominican Republic, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2026 Sails: Jan 17, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, 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, St Johns AG, Antigua, Gustavia, Philipsburg
2026 Sails: Jan 25, More...

7 Night - Windward & Leeward Islands Cruise
Starting in San Juan, White Bay, Jost van Dyke, Sint Eustatius, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Jan 25, More...

10 Night - Antigua to Grenada
Starting in St Johns AG, Gustavia, St Barts, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Admiralty Bay, Bequia, Grenadines, Tobago Cays, Grenadines, St Georges, Grenada
2026 Sails: Jan 28, More...

7 Night - Caribbean Island Adventure Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Trellis Bay, Beef Island, Sandy Ground, Gustavia, Philipsburg, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Norman Island, Charlotte Amalie, St Thomas
2026 Sails: Jan 31, More...

7 Night - Grand Island Adventure Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Sandy Ground, Gustavia, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Norman Island, Charlotte Amalie, St Thomas
2026 Sails: Feb 14, 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...

7 Night - Leeward Islands Adventure Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Charlestown, Nevis, Simpson Bay, Gustavia, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Norman Island, San Juan
2026 Sails: Mar 14, More...