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

7 Night - Eastern Caribbean with St. Barths
Starting in Marigot, Saint Martin, Marigot, Saint Martin / Prickly Pear Cays, Anguilla / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Charlestown, Saint Kitts and Nevis / Cades Bay, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 20, 2027: Jan 16, Feb 13, Mar 13, More...

7 Night - A Journey of Caribbean Celebrations & Island Wonders
Starting in San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 20, 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...

17 Night - Tropical Serenade
Starting in Miami, Cozumel, Mexico, Roatan, Harvest Caye, Costa Maya, Mexico, Miami, Charlotte Amalie, Philipsburg, Gustavia, Basseterre, Tortola, Miami
2026 Sails: Dec 21, More...

15 Night - Holiday Season with Your Toes in the Sand
Starting in Philipsburg, North Sound / Virgin Gorda, The Bight Bay / Norman Island, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Gustavia, Philipsburg
2026 Sails: Dec 21, More...

7 Night - History and Culture Visiting Caribbean Jewels
Starting in Marigot, Prickley Pear Cays, Gustavia, Charlestown, Nevis, Falmouth Bay, Barbuda, Les Saintes, Pointe-a-Pitre
2026 Sails: Dec 26, 2027: Jan 23, Feb 20, Mar 20, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Dec 26, More...

7 Night - Classic Caribbean
Starting in Philipsburg, St Maarten, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Philipsburg, St Maarten
2026 Sails: Dec 26, More...

13 Night - Discover the Grenadines & Windwards Islands
Starting in Bridgetown, Barbados, Bridgetown / Port St Charles, Barbados, Kingstown / Bequia Island, Saint Vincent and the Grenadines, Bequia Island / Mayreau Island, Saint Vincent and the Grenadines, Mayreau Island / Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island / Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Marigot, Saint Martin
2026 Sails: Dec 27, More...