14 Night - Barbados to Panama
Starting in Bridgetown, Barbados, Tobago Cays, Grenadines, St Georges, Grenada, Kralendijk, Bonaire, Willemstad AN, Curacao, Oranjestad, Aruba, Santa Marta, Colombia, Cartagena De Indias, Colombia, San Blas Archipelago, Panama, Panama Canal Transit, Balboa (Isla Flamenco), Panama
2026 Sails: Dec 5, More...

8 Night - Relax the Caribbean Way
Starting in Bridgetown, Port Elizabeth VC / Bequia, Tobago Cays, St Vincent and the Grenadines, St Georges, Saint-Pierre, Soufriere, Bridgetown
2026 Sails: Dec 8, Dec 15, More...

7 Night - Grenadine Islands
Starting in Bridgetown, Barbados, Captains Best, Grenadines, St Georges, Grenada, Tobago Cays, Grenadines, Kingstown, St Vincent (Morning), Admiralty Bay, Bequia (Pm), Fort-de-France, Martinique (Morning), Beach, Martinique (Afternoon), Marigot Bay, St Lucia (Am), Soufriere, St Lucia (Pm), Bridgetown, Barbados
2026 Sails: Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

7 Night - Pearls of the Caribbean
Starting in Fort-de-France, Union Island, Tobago Cays, Mayreau Island, Port Elizabeth VC, Bequia Island, Pigeon Island Beach, Soufriere, Les Saintes, Fort-de-France
2026 Sails: Dec 23, Dec 30, 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...

7 Night - Gliding the Waters of the Windward Islands
Starting in Pointe-a-Pitre, Portsmouth, Port Elizabeth VC, Bequia Island, Tobago Cays, Sandy Island, Carriacou, Sailing along the Pitons, Les Anses-dArlet, Marie-Galante, Pointe-a-Pitre
2027 Sails: Jan 2, Jan 30, Feb 27, Mar 27, More...

7 Night - Pearls of the Caribbean
Starting in Fort-de-France, Union Island, Tobago Cays, Mayreau Island, Port Elizabeth VC, Bequia Island, Pigeon Island Beach, Soufriere, Les Saintes, Fort-de-France
2027 Sails: Jan 6, Jan 20, Feb 3, More...

10 Night - Aruba to Grenada
Starting in Oranjestad, Aruba, Willemstad AN, Curacao, Charlestown Bay, Canouan, Grenadines, Tobago Cays, Grenadines, Admiralty Bay, Bequia, Grenadines, Charlotteville, Tobago, Castara Bay, Tobago, Saline Bay, Mayreau, Grenadines, St Georges, Grenada
2027 Sails: Jan 27, More...

11 Night - Grenada Roundtrip
Starting in St Georges, Grenada, Charlotteville, Tobago, Castara Bay, Tobago, Paradise Beach, Carriacou, Grenada, Tobago Cays, Grenadines, Charlestown Bay, Canouan, Grenadines, Admiralty Bay, Bequia, Grenadines, Saint-Pierre, Martinique, Soufriere, St Lucia, Bridgetown, Barbados, Saline Bay, Mayreau, Grenadines, St Georges, Grenada
2027 Sails: Feb 6, More...

7 Night - Cruising the Caribbean's Windward Islands - with Smithsonian Journeys
Starting in Vieux Fort, Portsmouth, Les Saintes, Port Elizabeth VC, Bequia Island, Mayreau Island, Tobago Cays, Bridgetown, Vieux Fort
2027 Sails: Feb 17, More...