EWR> Saint Thomas Island, U.S. Virgin Islands: Flight & 8 nights: $651- Apr-Jun 

EWR > Saint Thomas Island, U.S. Virgin Islands: Flight & 8 nights: $651- Apr-Jun 

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EWR> George Town, Cayman Islands: Flight & 7 nights: $739- Mar-May

EWR > George Town, Cayman Islands: Flight & 7 nights: $739- Mar-May

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LGA> Oranjestad, Aruba: Flight & 5 nights: $458- Mar-May 

LGA > Oranjestad, Aruba: Flight & 5 nights: $458- Mar-May 

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

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JFK> Grenada, Grenada: Flight & 7 nights: $498- May-Jul (Including Summer Break) 

JFK > Grenada, Grenada: Flight & 7 nights: $498- May-Jul (Including Summer Break) 

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LGA> Port Au Prince, Haiti: Flight & 6 nights: $473- Apr-Jun

LGA > Port Au Prince, Haiti: Flight & 6 nights: $473- Apr-Jun

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LGA> Piarco, Trinidad and Tobago: Flight & 4 nights: $492- Feb-Apr (Including Spring Break) 

LGA > Piarco, Trinidad and Tobago: Flight & 4 nights: $492- Feb-Apr (Including Spring Break) 

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EWR> Kingston, Jamaica: Flight & 5 nights: $389- Mar-May 

EWR > Kingston, Jamaica: Flight & 5 nights: $389- Mar-May 

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EWR> Simpson Bay, Sint Maarten: Flight & 4 nights: $475- Apr-Jun 

EWR > Simpson Bay, Sint Maarten: Flight & 4 nights: $475- Apr-Jun 

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EWR> Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $796- Feb-Apr (Including Spring Break) 

EWR > Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $796- Feb-Apr (Including Spring Break) 

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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JFK> Providenciales, Turks and Caicos Islands: Flight & 4 nights: $651- Mar-May 

JFK > Providenciales, Turks and Caicos Islands: Flight & 4 nights: $651- Mar-May 

Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…...

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EWR> Oranjestad, Aruba: Flight & 7 nights: $478- Apr-Jun 

EWR > Oranjestad, Aruba: Flight & 7 nights: $478- Apr-Jun 

EWR > Oranjestad, Aruba: $303 round-trip Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap…...

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JFK> Bridgetown, Barbados: Flight & 8 nights: $540- Mar-May

JFK > Bridgetown, Barbados: Flight & 8 nights: $540- Mar-May

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EWR > Luqa, Malta: Flight & 5 nights: $748- Mar-May 

EWR > Luqa, Malta: Flight & 5 nights: $748- Mar-May 

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JFK> Grenada, Grenada: Flight & 7 nights: $472- May-Jul (Including Summer Break) 

JFK > Grenada, Grenada: Flight & 7 nights: $472- May-Jul (Including Summer Break) 

* 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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LGA> Port Au Prince, Haiti: Flight & 9 nights: $784- Feb-Apr (Including Spring Break)

LGA > Port Au Prince, Haiti: Flight & 9 nights: $784- Feb-Apr (Including Spring Break)

* This is a “fare dump” with a few alternate dates available....

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JFK> Willemstad, Curaçao: Flight & 7 nights: $463- May-Jul (Including Summer Break) 

JFK > Willemstad, Curaçao: Flight & 7 nights: $463- May-Jul (Including Summer Break) 

* 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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EWR> Kingston, Jamaica: Flight & 3 nights: $391- Feb-Apr (Including Spring Break) 

EWR > Kingston, Jamaica: Flight & 3 nights: $391- Feb-Apr (Including Spring Break) 

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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EWR> Santo Domingo, Dominican Republic: Flight & 3 nights: $253- Feb-Apr (Including Spring Break)

EWR > Santo Domingo, Dominican Republic: Flight & 3 nights: $253- Feb-Apr (Including Spring Break)

* 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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EWR> George Town, Cayman Islands: Flight & 7 nights: $746- Mar-May 

EWR > George Town, Cayman Islands: Flight & 7 nights: $746- Mar-May 

* 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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EWR> Simpson Bay, Sint Maarten: Flight & 5 nights: $483- Mar-May

EWR > Simpson Bay, Sint Maarten: Flight & 5 nights: $483- Mar-May

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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EWR> Providenciales, Turks and Caicos Islands: Flight & 3 nights: $555- Feb-Apr (Including Spring Break) 

EWR > Providenciales, Turks and Caicos Islands: Flight & 3 nights: $555- Feb-Apr (Including Spring Break) 

Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…...

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LGA> Oranjestad, Aruba: Flight & 7 nights: $484- Mar-May

LGA > Oranjestad, Aruba: Flight & 7 nights: $484- Mar-May

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

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EWR> Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $783- Feb-Apr (Including Spring Break)

EWR > Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $783- Feb-Apr (Including Spring Break)

* 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> Hamilton, Bermuda: Flight & 3 nights: $532- Feb-Apr (Including Spring Break) 

JFK > Hamilton, Bermuda: Flight & 3 nights: $532- Feb-Apr (Including Spring Break) 

Years ago, we had a family reunion in Bermuda. Of all of the islands I’ve been to, Bermuda is one…...

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LGA > Cap Haitien, Haiti: Flight & 8 nights: $459- Feb-Apr

LGA > Cap Haitien, Haiti: Flight & 8 nights: $459- Feb-Apr

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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EWR> Willemstad, Curaçao: Flight & 8 nights: $508- Feb-Apr (Including Spring Break) 

EWR > Willemstad, Curaçao: Flight & 8 nights: $508- Feb-Apr (Including Spring Break) 

* 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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EWR> Santo Domingo, Dominican Republic: Flight & 9 nights: $327- Feb-Apr 

EWR > Santo Domingo, Dominican Republic: Flight & 9 nights: $327- Feb-Apr 

 * There only appear to be a few seats at this price and availability is spotty. It will take a…...

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EWR> Bridgetown, Barbados: Flight & 6 nights: $766- Feb-Apr 

EWR > Bridgetown, Barbados: Flight & 6 nights: $766- Feb-Apr 

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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EWR> Grenada, Grenada: Flight & 4 nights: $616- Feb-Apr (Including Spring Break) 

EWR > Grenada, Grenada: Flight & 4 nights: $616- Feb-Apr (Including Spring Break) 

* 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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EWR > Luqa, Malta: Flight & 5 nights: $781- Feb-Apr (Including Spring Break)

EWR > Luqa, Malta: Flight & 5 nights: $781- Feb-Apr (Including Spring Break)

* There only appear to be a few seats at this price and availability is spotty. It will take a…...

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JFK> George Town, Cayman Islands: Flight & 7 nights: $704- Mar-May

JFK > George Town, Cayman Islands: Flight & 7 nights: $704- Mar-May

* 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> Providenciales, Turks and Caicos Islands: Flight & 4 nights: $657- Mar-May 

JFK > Providenciales, Turks and Caicos Islands: Flight & 4 nights: $657- Mar-May 

Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. (Pictures included) * This is…...

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JFK> Piarco, Trinidad and Tobago: Flight & 5 nights: $519- Mar-May 

JFK > Piarco, Trinidad and Tobago: Flight & 5 nights: $519- Mar-May 

* 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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