7 Night - Windward & Leeward Islands Cruise
Starting in Charlotte Amalie, St Thomas, Prickly Pear, Sandy Ground, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Mar 15, More...

11 Night - Sailing On the Trade Winds
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Saint-Pierre, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Gustavia, Philipsburg
2026 Sails: Mar 16, More...

7 Night - History and Culture Visiting Caribbean Jewels
Starting in Philipsburg, Prickley Pear Cays, Gustavia, Charlestown, Nevis, Falmouth Bay, Barbuda, Les Saintes, Pointe-a-Pitre
2026 Sails: Mar 21, More...

7 Night - Antigua to Antigua
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, Philipsburg, St Maarten, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2026 Sails: Mar 21, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 21, More...

7 Night - Classic Caribbean
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 21, 2027: Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, Dec 12, Dec 27, 2028: Jan 9, Jan 23, Feb 6, Feb 20, Mar 5, More...

7 Night - Yachting the Bahama Archipelago Cruise
Starting in Bridgetown, Barbados, Le Marin, Terre De Haut, Iles des Saintes, Charlestown, Nevis, Simpson Bay, Gustavia, Prickly Pear, San Juan
2026 Sails: Mar 22, More...

14 Night - An Extended Journey of Tropical Radiance and Sun-Kissed Splendour
Starting in San Juan, Kralendijk, Willemstad AN, Oranjestad, St Maarten / Philipsburg, San Juan, St Johns AG, Antigua, Gustavia, Puerto Plata, Dominican Republic, Key West, Miami
2026 Sails: Mar 26, More...

17 Night - Star Collector : Seeking the Antilles
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Les Saintes, Pigeon Island, St Georges, Gustavia, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, Isla Catalina, Santo Domingo, Cartagena CO, San Blas, Panama, Colon
2026 Sails: Mar 27, More...

10 Night - Gems of the Leeward Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, St Johns, Les Saintes, Pigeon Island, St Georges, Gustavia, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Mar 27, More...