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

14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Spanish Town, Virgin Gorda, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Road Bay, Anguilla, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 6, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Dec 6, Dec 20, More...

14 Night - Caribbean Yacht Explorer
Starting in Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, 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: Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, Nov 27, 2028: Jan 15, Jan 29, Feb 12, Feb 26, More...

7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, Nov 27, 2028: Jan 15, Jan 29, Feb 12, Feb 26, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Philipsburg, St Maarten, Gustavia, St Barthelemy, Charlestown, Roseau, Dominica, Mayreau, Les Saintes, Guadeloupe, Basseterre, St Kitts, Philipsburg, St Maarten
2026 Sails: Dec 19, More...

7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Philipsburg, St Maarten
2026 Sails: Dec 19, More...

16 Night - Leeward Island Holiday
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Marigot, St Martin, Terre-de-Haut, Iles des Saintes, Guadeloupe, Fort-De-France, Martinique, Rodney Bay, Saint Lucia, Roseau, Dominica, Little Bay, Montserrat, St Johns AG, Antigua, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 20, More...

14 Night - Holiday Season with Your Toes in the Sand
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Gustavia, Philipsburg
2026 Sails: Dec 21, More...

13 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...