14 Night - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico, Tortola, British Virgin Islands, St Kitts, Dominica, Grenada, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 8, More...

7 Night - Cruise from St Maarten (Philipsburg) to St Thomas (Charlotte Amalie)
Starting in Philipsburg, Falmouth Bay, Charlestown, Nevis, Terre De Haut, Iles des Saintes, Saba, Gustavia, White Bay, Jost van Dyke, Charlotte Amalie, St Thomas
2026 Sails: Mar 8, More...

7 Night - A Journey from San Juan to Miami
Starting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 11, More...

15 Night - An Extended Journey of Paradise Beauty and Colourful Shores
Starting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Mar 11, More...

21 Night - Caribbean Roundtrip from Miami
Starting in Miami, FL, San Juan, Puerto Rico, St Johns AG, Antigua, Castries, St Lucia, Bridgetown, Barbados, Philipsburg, St Maarten, Road Town, Tortola, Miami, FL, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, FL
2026 Sails: Mar 12, More...

9 Night - Red Hot Sailing Club Voyage
Starting in Miami, Puerto Plata, Dominican Republic, St Johns AG, Antigua and Barbuda, Basseterre, Saint Kitts and Nevis, The Beach Club at Bimini, Bahamas, Miami
2026 Sails: Mar 12, More...

7 Night - Eastern Caribbean with St. Barths
Starting in Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Prickly Pear Cays, Anguilla, Marigot, Saint Martin
2026 Sails: Mar 14, Mar 28, More...

21 Night - Eastern & Southern Caribbean : Leeward & Abc Islands
Starting in Miami, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, Half Moon Cay, Bahamas, Miami, Florida, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Kralendijk, Bonaire, Willemstad AN, Curacao, Oranjestad, Aruba, Miami, Florida
2026 Sails: Mar 14, More...

11 Night - Eastern Caribbean : Windward & Leeward Islands
Starting in Miami, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Mar 14, More...

14 Night - Star Collector : Caribbean Explorations
Starting in 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, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, 2027: Feb 13, Mar 13, More...