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...

15 Night - An Extended Journey Into Island Bliss & Lively Celebrations
Starting in San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Isla Catalina, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Jost Van Dyke, Basseterre, Charlotte Amalie (Saint Thomas), San Juan
2026 Sails: Dec 20, More...

8 Night - A Journey of Tropical Festivities & Dazzling Island Beauty
Starting in Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan
2026 Sails: Dec 20, More...

16 Night - An Extended Journey Through Caribbean Rhythms and Festive Island Nights
Starting in Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan, St Johns AG, Antigua, Pointe-a-Pitre, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Samana, Puerto Plata, Dominican Republic, Miami
2026 Sails: Dec 20, 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...

7 Night - San Juan to San Juan
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Little Bay, Montserrat, Castries, St Lucia, Canouan, Sopers Hole, San Juan
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...

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...