12 Night - Miami to Miami
Starting in Miami, Fl, San Juan, St John VI, Gustavia, St Barthelemy, St Johns, Little Bay, Montserrat, St Kitts (Basseterre), Jost Van Dyke, British Virgin Islands, Miami, Fl
2026 Sails: Nov 18, More...

15 Night - Southern Caribbean in Depth
Starting in Miami, Florida, San Juan, Puerto Rico, Great Harbour, Jost van Dyke, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 20, More...

14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Spanish Town, Virgin Gorda, British Virgin Islands, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Nov 22, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Nov 28, More...

7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 28, More...

14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Spanish Town, Virgin Gorda, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Road Bay, Anguilla, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 6, More...

10 Night - Miami to San Juan
Starting in Miami, Fl, St John VI, Philipsburg, St Maarten, St Kitts (Basseterre), Les Saintes, Fort-de-France, Little Bay, Montserrat, Jost Van Dyke, British Virgin Islands, San Juan
2026 Sails: Dec 10, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, 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, Fort-de-France, Sopers Hole, San Juan
2026 Sails: Dec 20, More...