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Cruise Dates

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October 2026

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Hero of the Seas

Royal Caribbean

Nov 6, 2027 - Nov 13, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

Nov 15, 2027 - Nov 22, 2027 (7 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

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

Miami • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Miami

Average Starting Price

4% OFF

Nov 29, 2026 - Dec 11, 2026 (12 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale

Average Starting Price

Oct 2, 2027 - Oct 9, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 15, 2029 - Mar 29, 2029 (14 Nights)

Miami • George Town, Cayman Islands • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Fort-De-France, Martinique • Philipsburg, St. Maarten • Miami

Average Starting Price

$6,999pp

Jim's Onboard Credit

Norwegian Pearl

Norwegian Cruise Line

Feb 7, 2028 - Feb 18, 2028 (11 Nights)

Philadelphia • Philipsburg, St. Maarten • St. Lucia • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

Mar 25, 2028 - Apr 2, 2028 (8 Nights)

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$639pp

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!

Azamara Quest

Azamara

Dec 5, 2027 - Dec 19, 2027 (14 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

Jan 14, 2028 - Jan 24, 2028 (10 Nights)

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

Average Starting Price

$1,787pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Dec 18, 2027 - Dec 25, 2027 (7 Nights)

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

Average Starting Price

$1,809pp

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!

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