14 Night - Discover Eastern Caribbean & Grenadines
Starting in Bridgetown, Barbados, Bridgetown / Port St Charles, Barbados, Kingstown / Bequia Island, Saint Vincent and the Grenadines, Bequia Island / Mayreau Island, Saint Vincent and the Grenadines, Mayreau Island / Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island / Tobago Cays, Saint Vincent and the Grenadines, 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, Marigot, Saint Martin
2026 Sails: Nov 29, More...

14 Night - An Extended Journey Through Golden Shores & Island Grace
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan
2026 Sails: Nov 29, More...

21 Night - Eastern Caribbean : Antiqua, St. Lucia and Bahamas
Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, Fort-De-France, Martinique, Bridgetown, Barbados, Scarborough, Trinidad and Tobago, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, Key West, Florida, Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Road Town (Tortola), British Virgin Islands, San Juan, Puerto Rico, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 29, More...

8 Night - A Tall Ship's Dream Destination
Starting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Nov 29, More...

7 Night - San Juan & the Virgin Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot, St Martin, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

7 Night - Western Caribbean from Santo Domingo
Starting in Santo Domingo, Dominican Republic, Guadeloupe (Antilles), Martinique (Antilles), St Kitts (Antilles), Antigua (Antilles), Tortola, British Virgin Islands, Santo Domingo, Dominican Republic
2026 Sails: Nov 30, More...

13 Night - Discover the Vibes of the Caribbean
Starting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Nov 30, More...

4 Night - San Juan / San Juan
Starting in San Juan, Marigot, Falmouth Harbour, Antigua, Virgin Gorda, San Juan
2026 Sails: Nov 30, More...

21 Night - Eastern & Western Caribbean : Leeward Islands & Mexico
Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Roseau, Dominica, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Falmouth, Jamaica, Georgetown, Cayman Islands, Mahogany Bay, Roatan, Honduras, Belize City, Belize, Cozumel, Mexico, Fort Lauderdale, Florida
2026 Sails: Dec 1, More...