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Cruise Dates

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October 2026

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Celebrity Silhouette

Celebrity Cruises

Mar 26, 2028 - Apr 1, 2028 (6 Nights)

Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Nassau • Fort Lauderdale

Average Starting Price

Jun 11, 2027 - Jun 14, 2027 (3 Nights)

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

Average Starting Price

Nov 21, 2026 - Dec 5, 2026 (14 Nights)

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

Average Starting Price

$2,104pp

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!

Zuiderdam

Holland America Line

Dec 19, 2026 - Jan 2, 2027 (14 Nights)

Miami • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Key West, Florida • Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami

Average Starting Price

$2,389pp

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!

Nieuw Amsterdam

Holland America Line

Dec 20, 2026 - Dec 27, 2026 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale

Average Starting Price

$1,274pp

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!

Valiant Lady

Virgin Voyages

Jul 29, 2027 - Aug 2, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

$780pp

Jim's Onboard Credit

46% OFF

Margaritaville at Sea Paradise

Margaritaville at Sea

Jul 12, 2027 - Jul 16, 2027 (4 Nights)

Palm Beach • Key West, Florida • Freeport • Palm Beach

Average Starting Price

$279pp

Jim's Onboard Credit

53% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

Sep 13, 2027 - Sep 18, 2027 (5 Nights)

Miami • Key West, Florida • George Town, Cayman Islands • Miami

Average Starting Price

$399pp

Jim's Onboard Credit

44% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Aug 14, 2027 - Aug 21, 2027 (7 Nights)

Tampa • Key West, Florida • Roatan, Honduras • Belize City • Cozumel • Tampa

Average Starting Price

44% OFF

Nov 7, 2027 - Nov 14, 2027 (7 Nights)

New Orleans • Fun Day at Sea • Key West, Florida • Celebration Key • Nassau • Fun Day at Sea • Fun Day at Sea • New Orleans

Average Starting Price

Oct 5, 2028 - Oct 9, 2028 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

Feb 11, 2027 - Feb 15, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

$916pp

Jim's Onboard Credit

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