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...

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 - South Caribbean
Starting in Bridgetown, Barbados, Kingstown, St Vincent and the Grenadines, Saint Georges, Granada, Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, Road Town (Tortola), British Virgin Islands, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, St Johns AG, Antigua, Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, Port Castries, Santa Lucia, Bridgetown, Barbados
2026 Sails: Mar 17, More...

8 Night - San Juan / San Juan
Starting in San Juan, Canouan, Bridgetown, Les Anses-dArlet, Terre-De-Haut (Marina Day), St Johns AG, Virgin Gorda, San Juan
2026 Sails: Mar 20, More...

7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Road Town, Tortola, British Virgin Islands, Bridgetown, Barbados, Castries, Saint Lucia, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Mar 21, More...

7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Tortola, Basseterre, St Kitts and Nevis, St Johns AG, Antigua, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 22, More...