14 Night - Caribbean Cruise : Barbados, St. Lucia & St. Maarten
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 28, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, 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: Nov 28, More...

7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 28, 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 - San Juan & the Virgin Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot, St Martin, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

13 Night - Discover the Vibes of the Caribbean
Starting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Nov 30, More...

4 Night - San Juan / San Juan
Starting in San Juan, Marigot, Falmouth Harbour, Antigua, Virgin Gorda, San Juan
2026 Sails: Nov 30, More...

14 Night - South Caribbean
Starting in Bridgetown, Barbados, Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, Road Town (Tortola), British Virgin Islands, La Romana, Dominican Republic, Virgin Gorda, British Virgin Islands, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, Road Town (Tortola), British Virgin Islands, Catalina Island, Dominican Republic, La Romana, Dominican Republic, Catalina Island, Dominican Republic, Bridgetown, Barbados
2026 Sails: Dec 3, 2027: Feb 11, More...