7 Night - San Juan / San Juan
Starting in San Juan, Marigot, Terre-De-Haut (Marina Day), Portsmouth DM, Sandy Ground, Virgin Gorda, San Juan
2026 Sails: Dec 21, More...

14 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...

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...

11 Night - Best of Southern Caribbean
Starting in Fort Lauderdale, Florida, Philipsburg, St Maarten, St Johns AG, Antigua, Castries, St Lucia, Bridgetown, Barbados, Roseau, Dominica, Basseterre, St Kitts and Nevis, Fort Lauderdale, Florida
2026 Sails: Dec 24, 2027: Jan 4, Jan 25, Feb 15, Mar 29, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, 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
2026 Sails: Dec 26, More...

7 Night - Classic Caribbean
Starting in Philipsburg, St Maarten, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Philipsburg, St Maarten
2026 Sails: Dec 26, More...

14 Night - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, St Lucia, Barbados, San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Kitts, Dominica, Grenada, Barbados, San Juan, Puerto Rico
2026 Sails: Dec 27, More...

7 Night - Southern Caribbean Holiday
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, St Croix, US Virgin Islands, St Johns AG, Antigua, Roseau, Dominica, Philipsburg, St Maarten, San Juan, Puerto Rico
2026 Sails: Dec 27, More...

14 Night - South Caribbean
Starting in Bridgetown, Barbados, Kingstown, St Vincent and the Grenadines, Saint George, Grenada, Castries, Saint Lucia, Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, Philipsburg, St Maarten, St Johns AG, Antigua, Basseterre, St Kitts and Nevis, Roseau, Dominica, Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, Castries, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 29, More...