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Cruise Dates

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October 2026

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Norwegian Prima

Norwegian Cruise Line

Mar 18, 2028 - Mar 25, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Nov 20, 2028 - Nov 30, 2028 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • 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

49% OFF

Mar 21, 2028 - Apr 4, 2028 (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

Feb 20, 2028 - Feb 27, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 30, 2028 - Jan 6, 2029 (7 Nights)

San Juan del sur, Nicaragua • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Road Bay, Anguilla • Gustavia, St. Barts • St. Kitts • San Juan del sur, Nicaragua

Average Starting Price

$4,300pp

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!

Wind Surf

Windstar Cruises

Jan 9, 2028 - Jan 16, 2028 (7 Nights)

Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

Dec 22, 2026 - Jan 3, 2027 (12 Nights)

Fort Lauderdale • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

Dec 13, 2028 - Dec 23, 2028 (10 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Martinique • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Dec 1, 2028 - Dec 8, 2028 (7 Nights)

Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados

Average Starting Price

Feb 25, 2029 - Mar 4, 2029 (7 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

49% OFF

Jan 17, 2028 - Jan 31, 2028 (14 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • 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

Average Starting Price

$1,432pp

Jim's Onboard Credit

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