DEN > Simpson Bay, Sint Maarten: $238 round-trip- Aug-Oct

DEN > Simpson Bay, Sint Maarten: $238 round-trip- Aug-Oct

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DEN > George Town, Cayman Islands: $393 round-trip- Jul-Sep

DEN > George Town, Cayman Islands: $393 round-trip- Jul-Sep

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

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DEN > Saint Thomas Island, U.S. Virgin Islands: $311 round-trip- Aug-Oct

DEN > Saint Thomas Island, U.S. Virgin Islands: $311 round-trip- Aug-Oct

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DEN > San Juan, Puerto Rico: $281 round-trip- Sep-Nov

DEN > San Juan, Puerto Rico: $281 round-trip- 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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DEN > Oranjestad, Aruba: $306 round-trip- Aug-Oct

DEN > Oranjestad, Aruba: $306 round-trip- 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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DEN > Montego Bay, Jamaica: $418 round-trip- Aug-Oct

DEN > Montego Bay, Jamaica: $418 round-trip- Aug-Oct

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DEN > Piarco, Trinidad and Tobago: $486 round-trip- Aug-Oct

DEN > Piarco, Trinidad and Tobago: $486 round-trip- Aug-Oct

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DEN > Christiansted, U.S. Virgin Islands: $369 round-trip- Aug-Oct

DEN > Christiansted, U.S. Virgin Islands: $369 round-trip- Aug-Oct

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DEN > Simpson Bay, Sint Maarten: $272 round-trip- Aug-Oct

DEN > Simpson Bay, Sint Maarten: $272 round-trip- Aug-Oct

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DEN > Saint Thomas Island, U.S. Virgin Islands: $331 round-trip- Aug-Oct

DEN > Saint Thomas Island, U.S. Virgin Islands: $331 round-trip- Aug-Oct

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

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DEN > Kingston, Jamaica: $401 round-trip- Jul-Sep

DEN > Kingston, Jamaica: $401 round-trip- Jul-Sep

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DEN > Oranjestad, Aruba: $328 round-trip- Aug-Oct (Including Labor Day)

DEN > Oranjestad, Aruba: $328 round-trip- Aug-Oct (Including Labor Day)

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

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DEN > Simpson Bay, Sint Maarten: $359 round-trip- Jun-Aug (Including Summer Break)

DEN > Simpson Bay, Sint Maarten: $359 round-trip- Jun-Aug (Including Summer Break)

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DEN > George Town, Cayman Islands: $393 round-trip- Jul-Sep

DEN > George Town, Cayman Islands: $393 round-trip- Jul-Sep

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DEN > Saint Thomas Island, U.S. Virgin Islands: $349 round-trip- Aug-Oct

DEN > Saint Thomas Island, U.S. Virgin Islands: $349 round-trip- Aug-Oct

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DEN > San Juan, Puerto Rico: $330 round-trip- Oct-Dec

DEN > San Juan, Puerto Rico: $330 round-trip- Oct-Dec

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DEN > Hamilton, Bermuda: $362 round-trip- Oct-Dec

DEN > Hamilton, Bermuda: $362 round-trip- Oct-Dec

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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DEN > Montego Bay, Jamaica: $425 round-trip- May-Jul (Including Summer Break)

DEN > Montego Bay, Jamaica: $425 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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DEN > Kingston, Jamaica: $403 round-trip- May-Jul (Including Summer Break)

DEN > Kingston, Jamaica: $403 round-trip- May-Jul (Including Summer Break)

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

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DEN > Simpson Bay, Sint Maarten: $260 round-trip – May-Jul (Including Summer Break)

DEN > Simpson Bay, Sint Maarten: $260 round-trip – May-Jul (Including Summer Break)

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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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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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DEN > Oranjestad, Aruba: $366 round-trip – May-Jul (Including Summer Break)

DEN > Oranjestad, Aruba: $366 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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DEN > Montego Bay, Jamaica: $397 round-trip – Apr-Jun (Including Summer Break)

DEN > Montego Bay, Jamaica: $397 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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DEN > Simpson Bay, Sint Maarten: $273 round-trip- Apr-Jun

DEN > Simpson Bay, Sint Maarten: $273 round-trip- Apr-Jun

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DEN > George Town, Cayman Islands: $402 round-trip- Apr-Jun

DEN > George Town, Cayman Islands: $402 round-trip- Apr-Jun

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DEN > Piarco, Trinidad and Tobago: $521 round-trip- May-Jul (Including Summer Break)

DEN > Piarco, Trinidad and Tobago: $521 round-trip- May-Jul (Including Summer Break)

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DEN > Willemstad, Curaçao: $552 round-trip- Sep-Nov

DEN > Willemstad, Curaçao: $552 round-trip- Sep-Nov

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DEN > Christiansted, U.S. Virgin Islands: $278 round-trip- Apr-Jun

DEN > Christiansted, U.S. Virgin Islands: $278 round-trip- Apr-Jun

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