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Zuiderdam
Holland America Line
Dec 12, 2026 - Dec 26, 2026 (14 Nights)
Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Key West, Florida • Miami
Average Starting Price
$2,099pp
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!

4% OFF
Nieuw Amsterdam
Holland America Line
Nov 29, 2026 - Dec 11, 2026 (12 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
Average Starting Price
$1,294pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jun 3, 2027 - Jun 7, 2027 (4 Nights)
Miami • Key West, Florida • Bimini • Miami
Average Starting Price
$636pp
Jim's Onboard Credit
33% OFF
Margaritaville at Sea Paradise
Margaritaville at Sea
Oct 11, 2027 - Oct 15, 2027 (4 Nights)
Palm Beach • Key West, Florida • Freeport • Palm Beach
Average Starting Price
$209pp
Jim's Onboard Credit
56% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
May 29, 2027 - Jun 5, 2027 (7 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami
Average Starting Price
$699pp
Jim's Onboard Credit
42% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
Jul 31, 2027 - Aug 5, 2027 (5 Nights)
Tampa • Key West, Florida • Cozumel • Tampa
Average Starting Price
$599pp
Jim's Onboard Credit
43% OFF
Carnival Liberty
Carnival Cruise Line
Apr 11, 2027 - Apr 18, 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
$650pp
Jim's Onboard Credit
Resilient Lady
Virgin Voyages
Jul 13, 2028 - Jul 17, 2028 (4 Nights)
Miami • Key West, Florida • Bimini • Miami
Average Starting Price
$676pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 28, 2027 - Feb 1, 2027 (4 Nights)
Miami • Key West, Florida • Bimini • Miami
Average Starting Price
$596pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Dec 13, 2027 - Dec 17, 2027 (4 Nights)
Fort Lauderdale • Nassau • Key West, Florida • Fort Lauderdale
Average Starting Price
$509pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Key West, Florida • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,025pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 2, 2027 - Jan 23, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,709pp
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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