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Cruise Dates

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October 2026

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Volendam

Holland America Line

Dec 22, 2026 - Jan 5, 2027 (14 Nights)

Fort Lauderdale • Key West, Florida • Oranjestad, Aruba • Charlotteville, Tobago • Grenada • Bridgetown, Barbados • Castries, St. Lucia • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,664pp

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 11, 2026 - Dec 27, 2026 (16 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale

Average Starting Price

$2,439pp

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

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

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

40% OFF

Aug 14, 2027 - Aug 21, 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

Oct 15, 2027 - Oct 18, 2027 (3 Nights)

Fort Lauderdale • Key West, Florida • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

Dec 3, 2027 - Dec 10, 2027 (7 Nights)

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

Average Starting Price

$5,000pp

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!

Brilliance of the Seas

Royal Caribbean

Feb 22, 2027 - Feb 26, 2027 (4 Nights)

Fort Lauderdale • Perfect Day Cococay • Key West, Florida • Fort Lauderdale

Average Starting Price

Mar 22, 2028 - Apr 2, 2028 (11 Nights)

Miami • Key West, Florida • Tampa • Mobile, Alabama • New Orleans • New Orleans • New Orleans • Cozumel • Miami

Average Starting Price

Dec 19, 2026 - Jan 3, 2027 (15 Nights)

Miami • Key West, Florida • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • Panama Canal, Panama • Manta, Ecuador • Guayaquil, Ecuador • Lima, Peru • Lima, Peru

Average Starting Price

$4,399pp

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!