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October 2026

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Crown Princess

Princess Cruises

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

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

Average Starting Price

Dec 12, 2027 - Dec 22, 2027 (10 Nights)

Port Canaveral (Orlando), Florida • San Juan, Puerto Rico • St. Kitts • St. Lucia • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

Feb 19, 2028 - Feb 26, 2028 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Road Bay, Anguilla • Ocean Cay • Miami

Average Starting Price

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

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Dec 19, 2027 - Dec 28, 2027 (9 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$1,017pp

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!

Zuiderdam

Holland America Line

Apr 7, 2027 - Apr 17, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Miami

Average Starting Price

$2,004pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Celebrity Summit

Celebrity Cruises

Dec 26, 2027 - Jan 2, 2028 (7 Nights)

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

Average Starting Price

Mar 16, 2027 - Mar 27, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,219pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Norwegian Dawn

Norwegian Cruise Line

Jan 2, 2028 - Jan 14, 2028 (12 Nights)

Jacksonville • Great Stirrup Cay • Grand Bahama Island • Puerto Plata, Dominican Republic • Samana, Dominican Republic • Tortola • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Jacksonville

Average Starting Price

Oct 28, 2027 - Nov 14, 2027 (17 Nights)

New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

Mar 19, 2027 - Mar 27, 2027 (8 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2027 - Jan 2, 2028 (22 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$5,709pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

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