8 Night - A Tall Ship's Dream Destination
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, Gustavia, St Johns AG, Antigua, Philipsburg
2026 Sails: Dec 14, More...

8 Night - Caribbean Celebration Ii Cruise
Starting in San Juan, Gustavia, Sandy Ground, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Leverick Bay, Virgin Gorda, Cane Garden Bay, Tortola, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 19, More...

14 Night - Caribbean from Bridgetown to Santo Domingo
Starting in Bridgetown, Port Elizabeth VC / Bequia, St Georges, Tobago Cays, St Vincent and the Grenadines, Soufriere, Gustavia, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, North Sound / Virgin Gorda, Santo Domingo
2026 Sails: Dec 22, More...

7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Gustavia, St Barts, 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, Road Bay, Anguilla, Philipsburg, St Maarten
2026 Sails: Dec 26, 2027: Mar 20, More...

7 Night - Tropical New Year's Ii Explorer Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Gustavia, White Bay, Jost van Dyke, Charlotte Amalie, St Thomas
2026 Sails: Dec 27, More...

7 Night - St. Barths & Caribbean Gems Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Sandy Ground, Gustavia, Norman Island, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Charlotte Amalie, St Thomas
2027 Sails: Jan 3, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Gustavia, St Johns AG, Antigua, 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
2027 Sails: Jan 4, Jan 18, More...

7 Night - Leeward Islands Discovery Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Norman Island, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Jan 9, Feb 6, More...

7 Night - St. Barths & Caribbean Gems Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Marigot, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Charlotte Amalie, St Thomas
2027 Sails: Jan 10, More...

7 Night - Best of British Virgin Isles & St. Barths Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Marigot, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Jan 16, Jan 30, Mar 27, Apr 10, More...