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Cruise Dates

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October 2026

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Disney Destiny

Disney Cruise Line

Nov 15, 2027 - Nov 20, 2027 (5 Nights)

Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • Nassau • Fort Lauderdale

Average Starting Price

Nov 15, 2027 - Nov 19, 2027 (4 Nights)

Fort Lauderdale • Key West, Florida • Bimini • Fort Lauderdale

Average Starting Price

Nov 18, 2026 - Nov 22, 2026 (4 Nights)

Fort Lauderdale • Cozumel • Fort Lauderdale

Average Starting Price

Nov 28, 2026 - Dec 6, 2026 (8 Nights)

Fort Lauderdale • Willemstad, Curacao • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

Dec 22, 2026 - Jan 12, 2027 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale

Average Starting Price

$3,689pp

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!

Regal Princess

Princess Cruises

Feb 5, 2029 - Feb 19, 2029 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

$1,974pp

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!

Sky Princess

Princess Cruises

Feb 4, 2029 - Feb 11, 2029 (7 Nights)

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

Average Starting Price

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Fort Lauderdale • Cozumel • Belize City • Roatan, Honduras • Fort Lauderdale

Average Starting Price

$847pp

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!

Sun Princess

Princess Cruises

Jan 17, 2027 - Jan 31, 2027 (14 Nights)

Fort Lauderdale • Celebration Key • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Cozumel • Belize City • Roatan, Honduras • Fort Lauderdale

Average Starting Price

$1,638pp

Jim's Onboard Credit

Brilliance of the Seas

Royal Caribbean

Nov 27, 2026 - Nov 30, 2026 (3 Nights)

Fort Lauderdale • Grand Bahama Island • Nassau • Fort Lauderdale

Average Starting Price

Dec 26, 2026 - Jan 9, 2027 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale • Key West, Florida • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,394pp

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!

Oasis of the Seas

Royal Caribbean

Feb 26, 2027 - Mar 1, 2027 (3 Nights)

Fort Lauderdale • Nassau • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

$418pp

Jim's Onboard Credit

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