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Cruise Dates

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October 2026

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Emerald Princess

Princess Cruises

Mar 26, 2028 - Apr 2, 2028 (7 Nights)

San Juan, Puerto Rico • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • Fort Lauderdale

Average Starting Price

Dec 2, 2027 - Dec 11, 2027 (9 Nights)

Miami • Nassau • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Miami

Average Starting Price

25% OFF

Nov 11, 2026 - Nov 25, 2026 (14 Nights)

Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Miami

Average Starting Price

$4,875pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • Oranjestad, Aruba • Willemstad, Curacao • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Sep 11, 2027 - Sep 19, 2027 (8 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Miami

Average Starting Price

Jan 4, 2027 - Jan 13, 2027 (9 Nights)

Port Canaveral (Orlando), Florida • Bimini • Willemstad, Curacao • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

$1,098pp

Jim's Onboard Credit

FREE Specialty Dining Meal

26% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Dec 27, 2028 - Jan 8, 2029 (12 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Scarborough (Tobago), Trinidad and Tobago • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

$8,549pp

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!

Caribbean Princess

Princess Cruises

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

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

Feb 1, 2027 - Feb 13, 2027 (12 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$3,949pp

Jim's Onboard Credit

Norwegian Jewel

Norwegian Cruise Line

Mar 19, 2027 - Mar 29, 2027 (10 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$1,209pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

Dec 27, 2027 - Jan 4, 2028 (8 Nights)

Miami • Willemstad, Curacao • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Nassau • Miami

Average Starting Price

Dec 23, 2027 - Jan 5, 2028 (13 Nights)

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$2,308pp

Jim's Onboard Credit

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