JFK > Grenada, Grenada: Flight & 10 nights: $707 – Nov-Jan

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Port Au Prince, Haiti: Flight & 3 nights: $370 – Sep-Nov (Including Fall Break)

EWR > Port Au Prince, Haiti: Flight & 3 nights: $370 – Sep-Nov (Including Fall Break)

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Kingston, Jamaica: Flight & 9 nights: $611 – Oct-Dec

EWR > Kingston, Jamaica: Flight & 9 nights: $611 – Oct-Dec

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

LGA> Montego Bay, Jamaica: Flight & 7 nights: $494 – Nov-Jan

LGA > Montego Bay, Jamaica: Flight & 7 nights: $494 – Nov-Jan

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Oranjestad, Aruba: Flight & 7 nights: $473 – Oct-Dec

Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Christiansted, U.S. Virgin Islands: $240 round-trip

EWR > Christiansted, U.S. Virgin Islands: $240 round-trip

* This is a “fare dump” with a few alternate dates available. Newark to Christiansted, U.S. Virgin Islands: 7 night…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Pointe-a-Pitre, Guadeloupe: Flight & 4 nights: $298 – Oct-Dec

JFK > Pointe-a-Pitre, Guadeloupe: Flight & 4 nights: $298 – Oct-Dec

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> George Town, Cayman Islands: Flight & 7 nights: $639 – Oct-Dec

EWR > George Town, Cayman Islands: Flight & 7 nights: $639 – Oct-Dec

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Montego Bay, Jamaica: Flight & 7 nights: $526 – Sep-Nov (Including Fall Break)

EWR > Montego Bay, Jamaica: Flight & 7 nights: $526 – Sep-Nov (Including Fall Break)

* This is a “fare dump” with a few alternate dates available. Newark to Montego Bay, Jamaica: 7 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Bridgetown, Barbados: Flight & 9 nights: $787 – Dec-Feb

EWR > Bridgetown, Barbados: Flight & 9 nights: $787 – Dec-Feb

* This is a “fare dump” with a few alternate dates available. Newark to Bridgetown, Barbados: 9 night trip. Flight…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Fort-de-France, Martinique: Flight & 6 nights: $460 – Jan-Mar

JFK > Fort-de-France, Martinique: Flight & 6 nights: $460 – Jan-Mar

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Oranjestad, Aruba: Flight & 7 nights: $478 – Sep-Nov (Including Fall Break)

EWR > Oranjestad, Aruba: Flight & 7 nights: $478 – Sep-Nov (Including Fall Break)

Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> George Town, Cayman Islands: Flight & 4 nights: $483 – Oct-Dec

EWR > George Town, Cayman Islands: Flight & 4 nights: $483 – Oct-Dec

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

LGA> Kingston, Jamaica: Flight & 8 nights: $595 – Oct-Dec

LGA > Kingston, Jamaica: Flight & 8 nights: $595 – Oct-Dec

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK > Willemstad, Curaçao: Flight & 7 nights: $491 – Nov-Jan

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Grenada, Grenada: Flight & 7 nights: $977 – Jan-Mar (Including President’s Day Weekend)

JFK > Grenada, Grenada: Flight & 7 nights: $977 – Jan-Mar (Including President’s Day Weekend)

* This is a “fare dump” with a few alternate dates available. New York to Grenada, Grenada: 7 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Fort-de-France, Martinique: Flight & 5 nights: $371 – Nov-Jan

JFK > Fort-de-France, Martinique: Flight & 5 nights: $371 – Nov-Jan

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

LGA> Piarco, Trinidad and Tobago: Flight & 8 nights: $1,037 – Oct-Dec (Including Thanksgiving)

LGA > Piarco, Trinidad and Tobago: Flight & 8 nights: $1,037 – Oct-Dec (Including Thanksgiving)

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Cayman Brac, Cayman Islands: Flight & 5 nights: $883 – Aug-Oct

JFK > Cayman Brac, Cayman Islands: Flight & 5 nights: $883 – Aug-Oct

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Aguadilla, Puerto Rico: Flight & 8 nights: $655 – Oct-Dec

EWR > Aguadilla, Puerto Rico: Flight & 8 nights: $655 – Oct-Dec

* This is a “fare dump” with a few alternate dates available. Newark to Aguadilla, Puerto Rico: 8 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

LGA > Oranjestad, Aruba: Flight & 7 nights: $545 – Aug-Oct

Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Cap Haitien, Haiti: Flight & 4 nights: $526 – Aug-Oct

EWR > Cap Haitien, Haiti: Flight & 4 nights: $526 – Aug-Oct

* This is a “fare dump” with a few alternate dates available. Newark to Cap Haitien, Haiti: 4 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> George Town, Cayman Islands: Flight & 7 nights: $821 – Jan-Mar

EWR > George Town, Cayman Islands: Flight & 7 nights: $821 – Jan-Mar

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Kingston, Jamaica: Flight & 7 nights: $620 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Bridgetown, Barbados: Flight & 10 nights: $809 – Dec-Feb

* This is a “fare dump” with a few alternate dates available. Newark to Bridgetown, Barbados: 10 night trip. Flight…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Grenada, Grenada: Flight & 8 nights: $645 – Jan-Mar

JFK > Grenada, Grenada: Flight & 8 nights: $645 – Jan-Mar

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Fort-de-France, Martinique: Flight & 7 nights: $433 – Nov-Jan

JFK > Fort-de-France, Martinique: Flight & 7 nights: $433 – Nov-Jan

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Willemstad, Curaçao: Flight & 5 nights: $382 – Nov-Jan

JFK > Willemstad, Curaçao: Flight & 5 nights: $390- Nov-Jan

* This is the only date I found, and there only appear to be a few seats at this price.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Kingston, Jamaica: Flight & 5 nights: $548 – Sep-Nov

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Oranjestad, Aruba: Flight & 7 nights: $547 – Aug-Oct

EWR > Oranjestad, Aruba: Flight & 7 nights: $547 – Aug-Oct

Premium subscriber benefit: Click below and download a complimentary 7-night luxury lodging certificate good at over 3500 resorts worldwide. (All…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Port Au Prince, Haiti: Flight & 9 nights: $483 – Aug-Oct

EWR > Port Au Prince, Haiti: Flight & 9 nights: $483 – Aug-Oct

Premium subscriber benefit: Click below and download a complimentary 7-night luxury lodging certificate good at over 3500 resorts worldwide. (All…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Bridgetown, Barbados: Flight & 7 nights: $493 – Aug-Oct

JFK > Bridgetown, Barbados: Flight & 7 nights: $493 – Aug-Oct

* This is a “fare dump” with a few alternate dates available. New York to Bridgetown, Barbados: 7 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> George Town, Cayman Islands: Flight & 7 nights: $845

EWR > George Town, Cayman Islands: Flight & 7 nights: $845 – Dec-Feb

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK > Willemstad, Curaçao: Flight & 5 nights: $429 – Jan-Mar

* This is a “fare dump” with a few alternate dates available. New York to Willemstad, Curaçao: 5 night trip.…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Aguadilla, Puerto Rico: Flight & 3 nights: $343 – Aug-Oct

JFK > Aguadilla, Puerto Rico: Flight & 3 nights: $343 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Montego Bay, Jamaica: Flight & 4 nights: $431 – Aug-Oct

EWR > Montego Bay, Jamaica: Flight & 4 nights: $451 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR> Saint Thomas Island, U.S. Virgin Islands: Flight & 5 nights: $538 – Aug-Oct

EWR > Saint Thomas Island, U.S. Virgin Islands: Flight & 5 nights: $538 – Aug-Oct

* This is a “fare dump” with a few alternate dates available. Newark to Saint Thomas Island, U.S. Virgin Islands:…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

EWR > Kingston, Jamaica: Flight & 4 nights: $522 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

JFK> Simpson Bay, Sint Maarten: Flight & 7 nights: $633 – Aug-Oct

JFK > Simpson Bay, Sint Maarten: Flight & 7 nights: $633 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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JFK> St. John’s, Antigua and Barbuda: Flight & 7 nights: $545 – Aug-Oct

JFK > St. John’s, Antigua and Barbuda: Flight & 7 nights: $545 – Aug-Oct

* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…...


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Free subscribers can search for the above trip for free by searching themselves on Google Flights or Kayak.com during the recommended months mentioned above.

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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this: