LGA> Grenada, Grenada: $343 round-trip- Aug-Oct

LGA > Grenada, Grenada: $343 round-trip- 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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EWR> Santo Domingo, Dominican Republic: $243 round-trip- Aug-Oct

EWR > Santo Domingo, Dominican Republic: $243 round-trip- 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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EWR> Simpson Bay, Sint Maarten: $282 round-trip- Aug-Oct

EWR > Simpson Bay, Sint Maarten: $282 round-trip- Aug-Oct

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EWR> Piarco, Trinidad and Tobago: $369 round-trip- Aug-Oct

EWR > Piarco, Trinidad and Tobago: $369 round-trip- 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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EWR> George Town, Cayman Islands: $314 round-trip- Nov-Jan

EWR > George Town, Cayman Islands: $314 round-trip- 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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LGA> Oranjestad, Aruba: $303 round-trip- May-Jul (Including Summer Break)

LGA > Oranjestad, Aruba: $303 round-trip- May-Jul (Including Summer 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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EWR> Willemstad, Curaçao: $330 round-trip- Aug-Oct

EWR > Willemstad, Curaçao: $330 round-trip- Aug-Oct

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JFK> Grenada, Grenada: $329 round-trip- Aug-Oct

JFK > Grenada, Grenada: $329 round-trip- 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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LGA> Piarco, Trinidad and Tobago: $369 round-trip- Sep-Nov (Including Fall Break)

LGA > Piarco, Trinidad and Tobago: $369 round-trip- Sep-Nov (Including Fall 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: $305 round-trip- May-Jul (Including Summer Break)

EWR > George Town, Cayman Islands: $305 round-trip- 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> Simpson Bay, Sint Maarten: $253 round-trip- May-Jul (Including Summer Break)

LGA > Simpson Bay, Sint Maarten: $253 round-trip- May-Jul (Including Summer Break)

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

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IAH > San Juan, Puerto Rico: $227 round-trip – Aug-Oct

* There only appear to be a few seats at this price and availability is spotty. It will take a little digging to find dates other than the dates I found, but at this price, it’s well worth digging for. Houston to San Juan, Puerto Rico: 6 night trip. (B...

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LGA> Providenciales, Turks and Caicos Islands: $331 round-trip- Oct-Dec

LGA > Providenciales, Turks and Caicos Islands: $331 round-trip- Oct-Dec

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

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JFK> Willemstad, Curaçao: $302 round-trip- Sep-Nov

JFK > Willemstad, Curaçao: $302 round-trip- Sep-Nov

* 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: $368 round-trip- May-Jul (Including Summer Break)

EWR > Grenada, Grenada: $368 round-trip- 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> Montego Bay, Jamaica: $307 round-trip- Apr-Jun (Including Summer Break)

EWR > Montego Bay, Jamaica: $307 round-trip- Apr-Jun (Including Summer 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> Oranjestad, Aruba: $324 round-trip- May-Jul (Including Summer Break)

EWR > Oranjestad, Aruba: $324 round-trip- May-Jul (Including Summer 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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EWR> George Town, Cayman Islands: $302 round-trip- May-Jul (Including Summer Break)

EWR > George Town, Cayman Islands: $302 round-trip- 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> Piarco, Trinidad and Tobago: $374 round-trip- Apr-Jun

EWR > Piarco, Trinidad and Tobago: $374 round-trip- Apr-Jun

* 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: $279 round-trip- May-Jul (Including Summer Break)

EWR > Simpson Bay, Sint Maarten: $279 round-trip- May-Jul (Including Summer 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> Bridgetown, Barbados: $321 round-trip- May-Jul (Including Summer Break)

EWR > Bridgetown, Barbados: $321 round-trip- May-Jul (Including Summer Break)

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

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JFK> Providenciales, Turks and Caicos Islands: $305 round-trip- May-Jul (Including Summer Break)

JFK > Providenciales, Turks and Caicos Islands: $305 round-trip- May-Jul (Including Summer Break)

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

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EWR> Montego Bay, Jamaica: $304 round-trip- Apr-Jun

EWR > Montego Bay, Jamaica: $304 round-trip- Apr-Jun

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

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JFK> Grenada, Grenada: $355 round-trip- Aug-Oct

JFK > Grenada, Grenada: $355 round-trip- 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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EWR> Nassau, The Bahamas: $325 round-trip- Apr-Jun

EWR > Nassau, The Bahamas: $325 round-trip- Apr-Jun

* 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> George Town, Cayman Islands: $302 round-trip- Nov-Jan

JFK > George Town, Cayman Islands: $302 round-trip- 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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EWR> Piarco, Trinidad and Tobago: $374 round-trip- May-Jul (Including Summer Break)

EWR > Piarco, Trinidad and Tobago: $374 round-trip- 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> San Juan, Puerto Rico: $224 round-trip- Sep-Nov (Including Fall Break)

LGA > San Juan, Puerto Rico: $224 round-trip- Sep-Nov (Including Fall Break)

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

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LGA> Simpson Bay, Sint Maarten: $257 round-trip – Apr-Jun

LGA > Simpson Bay, Sint Maarten: $257 round-trip – Apr-Jun

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

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JFK> Kralendijk, Caribbean Netherlands: $579 round-trip- Oct-Dec

JFK > Kralendijk, Caribbean Netherlands: $579 round-trip- Oct-Dec

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

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EWR> Port Au Prince, Haiti: $315 round-trip- Apr-Jun

EWR > Port Au Prince, Haiti: $315 round-trip- Apr-Jun

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

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LGA> Willemstad, Curaçao: $330 round-trip- Apr-Jun

LGA > Willemstad, Curaçao: $330 round-trip- Apr-Jun

* 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: $336 round-trip- Apr-Jun (Including Summer Break)

EWR > Kingston, Jamaica: $336 round-trip- Apr-Jun (Including Summer 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: $313 round-trip- Aug-Oct

JFK > Providenciales, Turks and Caicos Islands: $313 round-trip- Aug-Oct

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

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JFK> Grenada, Grenada: $355 round-trip- May-Jul (Including Summer Break)

JFK > Grenada, Grenada: $355 round-trip- 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> George Town, Cayman Islands: $302 round-trip- Apr-Jun

EWR > George Town, Cayman Islands: $302 round-trip- Apr-Jun

* 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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