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Cruise Dates

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October 2026

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Windstar Cruises

Feb 14, 2028 - Feb 28, 2028 (14 Nights)

San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

Jan 30, 2028 - Feb 13, 2028 (14 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Mar 20, 2027 - Mar 29, 2027 (9 Nights)

St. Martin • Frenchman's Cay, British Virgin Islands • St. Kitts • Les Trois-Îlets • Port Elizabeth, South Africa • Grenada • Bridgetown, Barbados • St. Lucia • Madeira (Funchal), Portugal • Portimão, Portugal • Lisbon, Portugal

Average Starting Price

Nov 29, 2026 - Dec 13, 2026 (14 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

Feb 17, 2029 - Feb 27, 2029 (10 Nights)

San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Grenada • Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Roseau, Dominica • Little Bay, Montserrat • St. Kitts • San Juan del sur, Nicaragua

Average Starting Price

21% OFF

Mar 9, 2027 - Mar 23, 2027 (14 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Jan 10, 2028 - Jan 22, 2028 (12 Nights)

Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Gustavia, St. Barts • Charlestown, Nevis • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados

Average Starting Price

Jan 17, 2027 - Jan 31, 2027 (14 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

49% OFF

Dec 28, 2027 - Jan 11, 2028 (14 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

$2,739pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

49% OFF

MSC Opera

MSC Cruises

Dec 13, 2027 - Dec 27, 2027 (14 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic

Average Starting Price

$2,002pp

Jim's Onboard Credit

30% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 8, 2029 - Jan 18, 2029 (10 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Feb 21, 2028 - Mar 13, 2028 (21 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Funchal, Portugal • Casablanca, Morocco • Lisbon, Portugal

Average Starting Price

$4,271pp

Jim's Onboard Credit

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