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October 2026

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Celebrity Eclipse

Celebrity Cruises

Apr 22, 2028 - May 8, 2028 (16 Nights)

Fort Lauderdale • Key West, Florida • Royal Naval Dockyard, Bermuda • Casablanca, Morocco • Cadiz, Spain • Malaga, Spain • Alicante, Spain • Palma de Mallorca, Spain • Barcelona, Spain

Average Starting Price

19% OFF

Jan 2, 2027 - Jan 9, 2027 (7 Nights)

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

Average Starting Price

$569pp

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 Reflection

Celebrity Cruises

May 28, 2027 - May 31, 2027 (3 Nights)

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

Average Starting Price

$468pp

Jim's Onboard Credit

32% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Nov 18, 2028 - Nov 25, 2028 (7 Nights)

Miami • Key West, Florida • Harvest Caye, Belize • Roatan, Honduras • Cozumel • Miami

Average Starting Price

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

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

Oct 7, 2027 - Oct 11, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

Nov 29, 2026 - Dec 20, 2026 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,164pp

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

Mar 13, 2027 - Mar 28, 2027 (15 Nights)

Miami • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Miami • Key West, Florida • Relaxaway Half Moon Cay • Miami

Average Starting Price

$2,974pp

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!

31% OFF

Carnival Breeze

Carnival Cruise Line

Jun 19, 2027 - Jun 26, 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

2% OFF

Feb 20, 2027 - Feb 28, 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

$656pp

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!

Silver Shadow

Silversea

Dec 10, 2027 - Dec 17, 2027 (7 Nights)

Miami • Grand Turk • Exuma Island, Bahamas • Key West, Florida • Bimini • Miami

Average Starting Price

$5,250pp

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!

6% OFF

Margaritaville at Sea Paradise

Margaritaville at Sea

Sep 13, 2027 - Sep 17, 2027 (4 Nights)

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

Average Starting Price

$159pp

Jim's Onboard Credit

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