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Cruise Dates

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October 2026

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Brilliant Lady

Virgin Voyages

Jan 21, 2027 - Jan 25, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

Jan 29, 2027 - Feb 12, 2027 (14 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico

Average Starting Price

$13,000pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Jan 2, 2028 - Jan 9, 2028 (7 Nights)

Tampa • Bimini • Grand Bahama Island • Key West, Florida • Tampa

Average Starting Price

Jul 2, 2027 - Jul 5, 2027 (3 Nights)

Fort Lauderdale • Key West, Florida • Grand Bahama Island • Fort Lauderdale

Average Starting Price

Apr 1, 2028 - Apr 8, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami

Average Starting Price

May 20, 2027 - May 24, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

5% OFF

Nov 21, 2026 - Nov 28, 2026 (7 Nights)

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

Average Starting Price

$734pp

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 - Jan 8, 2027 (19 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

$3,404pp

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!

Resilient Lady

Virgin Voyages

Jan 24, 2027 - Jan 30, 2027 (6 Nights)

Miami • Key West, Florida • Grand Turk • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$834pp

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!

Scarlet Lady

Virgin Voyages

Feb 25, 2027 - Mar 1, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

$636pp

Jim's Onboard Credit

46% OFF

Margaritaville at Sea Paradise

Margaritaville at Sea

Jun 28, 2027 - Jul 2, 2027 (4 Nights)

Palm Beach • Key West, Florida • Bimini • Palm Beach

Average Starting Price

$299pp

Jim's Onboard Credit

58% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Jul 3, 2027 - Jul 8, 2027 (5 Nights)

Tampa • Key West, Florida • Cozumel • Tampa

Average Starting Price

$599pp

Jim's Onboard Credit

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