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Celebrity Apex
Celebrity Cruises
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Key West, Florida • Cozumel • George Town, Cayman Islands • Port Canaveral (Orlando), Florida
Average Starting Price
$826pp
Jim's Onboard Credit
57% OFF
Carnival Spirit
Carnival Cruise Line
Jan 3, 2027 - Jan 11, 2027 (8 Nights)
Mobile, Alabama • Fun Day at Sea • Key West, Florida • Celebration Key • Relaxaway Half Moon Cay • Nassau • Fun Day at Sea • Fun Day at Sea • Mobile, Alabama
Average Starting Price
$490pp
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!

Rotterdam
Holland America Line
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!

Celebrity Summit
Celebrity Cruises
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Tampa • Key West, Florida • Bimini • Nassau • Tampa
Average Starting Price
$1,411pp
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!

Norwegian Dawn
Norwegian Cruise Line
Nov 30, 2026 - Dec 5, 2026 (5 Nights)
Jacksonville • Grand Bahama Island • Great Stirrup Cay • Key West, Florida • Jacksonville
Average Starting Price
$339pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 21, 2027 - Feb 5, 2027 (15 Nights)
Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami
Average Starting Price
$9,880pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Jan 16, 2028 - Jan 22, 2028 (6 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Nassau • Fort Lauderdale
Average Starting Price
$706pp
Jim's Onboard Credit
Celebrity Reflection
Celebrity Cruises
Jul 30, 2027 - Aug 2, 2027 (3 Nights)
Fort Lauderdale • Key West, Florida • Grand Bahama Island • Fort Lauderdale
Average Starting Price
$391pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Dec 10, 2026 - Dec 14, 2026 (4 Nights)
Miami • Key West, Florida • Bimini • Miami
Average Starting Price
$556pp
Jim's Onboard Credit
50% OFF
Carnival Dream
Carnival Cruise Line
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Galveston • Fun Day at Sea • Key West, Florida • Celebration Key • Nassau • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$596pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
Tampa • Bimini • Key West, Florida • George Town, Cayman Islands • Tampa
Average Starting Price
$642pp
Jim's Onboard Credit
Eurodam
Holland America Line
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!

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