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Cruise Dates

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October 2026

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Rotterdam

Holland America Line

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!

48% OFF

MSC Seashore

MSC Cruises

Jul 4, 2027 - Jul 8, 2027 (4 Nights)

Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Ocean Cay • Port Canaveral (Orlando), Florida

Average Starting Price

$451pp

Jim's Onboard Credit

57% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Apr 5, 2027 - Apr 10, 2027 (5 Nights)

Tampa • Key West, Florida • Freeport • Tampa

Average Starting Price

36% OFF

Aug 5, 2027 - Aug 9, 2027 (4 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Relaxaway Half Moon Cay • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

$518pp

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 Aura

Norwegian Cruise Line

Jul 24, 2027 - Jul 31, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami

Average Starting Price

Aug 1, 2027 - Aug 8, 2027 (7 Nights)

Miami • Costa Maya • Roatan, Honduras • Cozumel • Perfect Day Cococay • Miami

Average Starting Price

27% OFF

Jul 24, 2027 - Aug 1, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

68% OFF

Dec 13, 2026 - Dec 19, 2026 (6 Nights)

Tampa • Fun Day at Sea • Relaxaway Half Moon Cay • Celebration Key • Nassau • Fun Day at Sea • Tampa

Average Starting Price

$285pp

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!

Caribbean Princess

Princess Cruises

Jan 4, 2028 - Jan 13, 2028 (9 Nights)

Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort Lauderdale

Average Starting Price

$704pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Celebrity Constellation

Celebrity Cruises

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

Tampa • Costa Maya • Belize City • Bimini • Tampa

Average Starting Price

$1,058pp

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!