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...

14 Night - Caribbean Roundtrip from San Juan
Starting in San Juan, Jost Van Dyke, Little Bay, Castries, Fort-de-France, Sopers Hole, San Juan, St John VI, St Kitts, Les Saintes, Bequia, St Thomas, San Juan
2026 Sails: Dec 20, More...

15 Night - Holiday Season with Your Toes in the Sand
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Gustavia, Philipsburg
2026 Sails: Dec 21, More...

8 Night - Bridgetown to San Juan
Starting in Bridgetown, Soufriere, St Lucia, Bequia, St Georges, Fort-de-France, St Kitts (Basseterre), St Thomas, San Juan
2026 Sails: Dec 21, More...

12 Night - Ultimate Southern Caribbean
Starting in Fort Lauderdale, Florida, Basseterre, St Kitts and Nevis, Castries, St Lucia, Bridgetown, Barbados, Willemstad AN, Curacao, Kralendijk, Bonaire, Oranjestad, Aruba, Fort Lauderdale, Florida
2026 Sails: Dec 22, 2027: Jan 17, Feb 28, Apr 11, More...

21 Night - Eastern & Western Caribbean Holiday : Belize & Mexico
Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, Basseterre, St Kitts and Nevis, Roseau, Dominica, Castries, Saint Lucia, St Johns AG, Antigua, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Falmouth, Jamaica, Georgetown, Cayman Islands, Belize City, Belize, Cozumel, Mexico, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Dec 22, More...

11 Night - Eastern Caribbean Holiday : Windward & Leeward Islands
Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, Basseterre, St Kitts and Nevis, Roseau, Dominica, Castries, Saint Lucia, St Johns AG, Antigua, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Dec 22, More...

14 Night - Southern Caribbean : Abc & Windward Islands Holiday
Starting in Fort Lauderdale, Florida, Key West, Florida, Oranjestad, Aruba, Charlotteville, Trinidad and Tobago, Saint Georges, Grenada, Bridgetown, Barbados, Castries, Saint Lucia, San Juan, Puerto Rico, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Dec 22, More...

14 Night - Caribbean from Bridgetown to Santo Domingo
Starting in Bridgetown, Port Elizabeth VC / Bequia, St Georges, Tobago Cays, St Vincent and the Grenadines, Soufriere, Gustavia, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, North Sound / Virgin Gorda, Santo Domingo
2026 Sails: Dec 22, More...