7 Night - Philipsburg to Philipsburg
Starting in Philipsburg, St Maarten, St Johns, St Thomas, Little Bay, Montserrat, Castries, St Lucia, Bequia, Les Saintes, Philipsburg, St Maarten
2026 Sails: Jan 11, More...

7 Night - Lush & Lovely Islands of the Lesser Antilles
Starting in Philipsburg, St Maarten, Basseterre, Gustavia, St Johns, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Jan 11, More...

10 Night - Blue Waters of the Leeward Islands
Starting in Philipsburg, St Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 14, More...

12 Night - Panama, Colombia & Caribbean Islands
Starting in Colon, Portobelo, San Blas Islands, Cartagena CO, Santa Marta, Willemstad AN, Mayreau Island, Union Island, Pigeon Island Beach, Soufriere, Les Saintes, Fort-de-France
2026 Sails: Jan 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: Jan 24, More...

7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, Bequia, Mayreau, Soufriere, Les Saintes, Marigot, St Martin, San Juan
2026 Sails: Jan 30, Feb 13, More...

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

12 Night - The Essentials of the Caribbean
Starting in Fort-de-France, Antigua, South Friars Bay, Saint-Kitts, Jost Van Dyke, Gustavia, Les Saintes, Portsmouth UK, Pigeon Island Beach, Soufriere, Tobago Cays, Mayreau Island, Port Elizabeth VC, Bequia Island, Union Island, Fort-de-France
2026 Sails: Feb 10, More...

7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, Philipsburg, St Maarten, Les Saintes, Mayreau, Bequia, Soufriere, San Juan
2026 Sails: Feb 27, More...

8 Night - Cruising the Caribbean's Windward Islands - with Smithsonian Journeys
Starting in Vieux Fort, Portsmouth UK, Les Saintes, Port Elizabeth VC, Bequia Island, Mayreau Island, Saint Georges, Grenada, Tobago Cays, Bridgetown, Vieux Fort
2026 Sails: Feb 28, More...