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Cruise Dates

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October 2026

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Windstar Cruises

Feb 22, 2027 - Mar 2, 2027 (8 Nights)

Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Rodney Bay, Saint Lucia • Scenic Cruising the Pitons • Mayreau Island, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

55% OFF

Mar 21, 2027 - Apr 14, 2027 (24 Nights)

Valparaíso, Chile • Paracas, Peru • Paracas, Peru • Salaverry (Trujillo), Peru • Manta, Ecuador • Utria Natinal Park (Nuqui Harbour), Colombia • Darien National Park, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Guna Yala, San Blas Islands, Panama • Cartagena, Colombia • Cartagena, Colombia • Cabo de La Vela, Colombia • Willemstad, Curacao • Tobago Cays, Grenadines • Mayreau Island, Saint Vincent and the Grenadines • Soufrier Bay, St. Lucia • Bridgetown, Barbados

Average Starting Price

Jan 22, 2028 - Jan 30, 2028 (8 Nights)

Fort Lauderdale • Willemstad, Curacao • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

$1,698pp

Jim's Onboard Credit

Norwegian Joy

Norwegian Cruise Line

Apr 8, 2028 - Apr 17, 2028 (9 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Falmouth, Jamaica • Miami

Average Starting Price

55% OFF

Mar 20, 2027 - Mar 28, 2027 (8 Nights)

Miami • Celebration Key • Fun Day at Sea • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

41% OFF

Nov 21, 2026 - Nov 29, 2026 (8 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$825pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Dec 10, 2026 - Dec 21, 2026 (11 Nights)

Tampa • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Tampa

Average Starting Price

Dec 6, 2026 - Dec 20, 2026 (14 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Amber Cove, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

$1,015pp

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!

49% OFF

MSC Poesia

MSC Cruises

Dec 23, 2027 - Jan 2, 2028 (10 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Ocho Rios, Jamaica • Miami

Average Starting Price

$1,749pp

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!