15 Night - An Extended Journey of Fabled Ports, Volcanic Isles and Soft Sands
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 13, More...

7 Night - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Norman Island, Cooper Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Jan 17, More...

7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, 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, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Jan 18, More...

14 Night - An Extended Journey Between Sophistication & Silky Sands
Starting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...

7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...

15 Night - An Extended Journey of Caribbean Inspiration and Island Beauty
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, 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 - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 24, More...

7 Night - San Juan / San Juan
Starting in San Juan, Soufriere, Canouan, Portsmouth DM, Sandy Ground, Gustavia, San Juan
2026 Sails: Jan 25, More...