IND> Montego Bay, Jamaica: Flight & 4 nights: $609- Apr-Jun

IND > Montego Bay, Jamaica: Flight & 4 nights: $609- Apr-Jun

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IND> George Town, Cayman Islands: Flight & 6 nights: $1,078- Jan-Mar

IND > George Town, Cayman Islands: Flight & 6 nights: $1,078- 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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IND> San Diego, California: $107 round-trip- Jan-Mar

IND > San Diego, California: $107 round-trip- Jan-Mar

IND > San Diego, California: Flight & 3 nights: $222 Have friends or family in San Diego? Grab this cheap…...

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IND > Larnaca, Cyprus: Flight & 4 nights: $684- Dec-Feb 

IND > Larnaca, Cyprus: Flight & 4 nights: $684- Dec-Feb 

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

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IND> Oranjestad, Aruba: Flight & 5 nights: $523- Feb-Apr (Including Spring Break) 

IND > Oranjestad, Aruba: Flight & 5 nights: $523- Feb-Apr (Including Spring 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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IND > Fort Myers, Florida: $77 round-trip – Dec-Feb

IND > Fort Myers, Florida: $77 round-trip – Dec-Feb

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IND> Belize City, Belize: Flight & 6 nights: $503 – Dec-Feb 

IND > Belize City, Belize: Flight & 6 nights: $503 – 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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IND> Panama City, Panama: Flight & 9 nights: $1,150 – Dec-Feb

IND > Panama City, Panama: Flight & 9 nights: $1,150 – Dec-Feb

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

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IND> Providenciales, Turks and Caicos Islands: Flight & 3 nights: $773

IND > Providenciales, Turks and Caicos Islands: Flight & 3 nights: $773 – May-Jul 

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

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IND> Cancun, Mexico: Flight & 8 nights: $351 – Jan-Mar

IND > Cancun, Mexico: Flight & 8 nights: $351 – Jan-Mar

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IND> Kralendijk, Caribbean Netherlands: Flight & 8 nights: $793 – Jan-Mar

IND > Kralendijk, Caribbean Netherlands: Flight & 8 nights: $793 – 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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IND> Charleston, South Carolina: $134 round-trip

IND > Charleston, South Carolina: $109 round-trip – Apr-Jun

Have friends or family in Charleston? Grab this cheap flight and visit them, or check out the reverse search link…...

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IND > San Juan, Puerto Rico: Flight & 9 nights: $504 – Jan-Mar

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

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– Dec-Feb IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $885

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $885 – Dec-Feb

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

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IND> Pointe-a-Pitre, Guadeloupe: Flight & 7 nights: $727 – Dec-Feb

IND > Pointe-a-Pitre, Guadeloupe: Flight & 7 nights: $727 – Dec-Feb

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

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IND> Montego Bay, Jamaica: Flight & 5 nights: $660 -Jan- Mar 

IND > Montego Bay, Jamaica: Flight & 5 nights: $660 -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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– Jan-Mar IND> George Town, Cayman Islands: Flight & 7 nights: $981

IND > George Town, Cayman Islands: Flight & 7 nights: $981 – 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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IND > Santo Domingo, Dominican Republic: Flight & 3 nights: $684 – Dec-Feb

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

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IND > Belize City, Belize: Flight & 8 nights: $564 – Jan-Mar (Including President’s Day Weekend)

* 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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IND> Boston, Massachusetts: $177 round-trip – Apr-Jun

IND > Boston, Massachusetts: $177 round-trip – Apr-Jun

I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…...

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IND> Tegucigalpa, Honduras: Flight & 13 nights: $907 – Feb-Apr (Including Spring Break)

IND > Tegucigalpa, Honduras: Flight & 13 nights: $907 – 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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IND> San Diego, California: $140 round-trip – Nov-Jan 

IND > San Diego, California: $140 round-trip – Nov-Jan 

Have friends or family in San Diego? Grab this cheap flight and visit them, or check out the reverse search…...

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IND > Panama City, Panama: Flight & 6 nights: $829 – Jan-Mar (Including President’s Day Weekend)

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

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IND> Providenciales, Turks and Caicos Islands: $368 round-trip – Dec-Feb

IND > Providenciales, Turks and Caicos Islands: $368 round-trip – Dec-Feb

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

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IND> Orlando, Florida: $87 round-trip – Nov-Jan

IND > Orlando, Florida: $87 round-trip – Nov-Jan (Including Winter Break)

Have friends or family in Orlando? Grab this cheap flight and visit them, or check out the reverse search link…...

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IND> Oranjestad, Aruba: Flight & 5 nights: $602 – Feb-Apr (Including Spring Break)

IND > Oranjestad, Aruba: Flight & 5 nights: $602 – Feb-Apr (Including Spring 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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IND> Cancun, Mexico: Flight & 7 nights: $330 – Dec-Feb

IND > Cancun, Mexico: Flight & 7 nights: $330 – Dec-Feb

Premium subscriber benefit: Log in and click below to download a 6-night luxury vacation voucher for Mayan Palace in Mazatlan,…...

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IND> San Juan, Puerto Rico: Flight & 6 nights: $452 – Feb-Apr

IND > San Juan, Puerto Rico: Flight & 6 nights: $452 – Feb-Apr

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

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IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 9 nights: 1254 – Dec-Feb (Including MLK Weekend)

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 9 nights: 1254 – Dec-Feb (Including MLK Weekend)

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

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IND> Luqa, Malta: Flight & 5 nights: $768 – Jan-Mar

IND > Luqa, Malta: Flight & 5 nights: $768 – Jan-Mar

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

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IND > Toronto, Canada: Flight & 3 nights: $276 – Jan-Mar 

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

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IND> Sydney, Australia: Flight & 9 nights: $1,165 – Feb-Apr 

IND > Sydney, Australia: Flight & 9 nights: $1,165 – Feb-Apr 

* 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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IND> Dublin, Ireland: Flight & 7 nights: $736 – Jan-Mar

IND > Dublin, Ireland: Flight & 7 nights: $736 – Jan-Mar (Including President’s Day Weekend)

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

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IND> Nassau, The Bahamas: Flight & 5 nights: $580 – Feb-Apr

IND > Nassau, The Bahamas: Flight & 5 nights: $580 – Feb-Apr

* 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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IND> San Jose, Costa Rica: Flight & 4 nights: $562

IND > San Jose, Costa Rica: Flight & 4 nights: $562 – Oct-Dec (Including Thanksgiving)

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

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IND> Montego Bay, Jamaica: Flight & 4 nights: $616 – Jan-Mar

IND > Montego Bay, Jamaica: Flight & 4 nights: $616 – 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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IND> Piarco, Trinidad and Tobago: Flight & 3 nights: $840 – Dec-Feb (Including MLK Weekend)

IND > Piarco, Trinidad and Tobago: Flight & 3 nights: $840 – Dec-Feb (Including MLK Weekend)

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

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It's like having your own personal assistant...
who works for $.26 per day...
every day of the week...
and alerts you of the best travel deals on the internet...
and gives you one-click access to every detail you need...
to make sure you find your dream trip BEFORE it sells out...
(because they ALWAYS sell out. Sometimes within hours.)

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(Including Winter Break) IND> Kralendijk, Caribbean Netherlands: Flight & 7 nights: $419 – Dec-Feb

IND > Kralendijk, Caribbean Netherlands: Flight & 7 nights: $419 – Dec-Feb

*This is a rarely found “flight + hotel” mistake worth looking into. The flight price isn’t all that great, but…...

Non-members can search Kayak.com for this trip during the recommended months for free.
Not a member yet? Become one today.
It's like having your own personal assistant...
who works for $.26 per day...
every day of the week...
and alerts you of the best travel deals on the internet...
and gives you one-click access to every detail you need...
to make sure you find your dream trip BEFORE it sells out...
(because they ALWAYS sell out. Sometimes within hours.)

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IND > George Town, Cayman Islands: Flight & 3 nights: $666 – Dec-Feb (Including MLK Weekend)

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

Non-members can search Kayak.com for this trip during the recommended months for free.
Not a member yet? Become one today.
It's like having your own personal assistant...
who works for $.26 per day...
every day of the week...
and alerts you of the best travel deals on the internet...
and gives you one-click access to every detail you need...
to make sure you find your dream trip BEFORE it sells out...
(because they ALWAYS sell out. Sometimes within hours.)

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IND> Belize City, Belize: Flight & 7 nights: $618 – Jan-Mar

IND > Belize City, Belize: Flight & 7 nights: $618 – Jan-Mar

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

Non-members can search Kayak.com for this trip during the recommended months for free.
Not a member yet? Become one today.
It's like having your own personal assistant...
who works for $.26 per day...
every day of the week...
and alerts you of the best travel deals on the internet...
and gives you one-click access to every detail you need...
to make sure you find your dream trip BEFORE it sells out...
(because they ALWAYS sell out. Sometimes within hours.)

Upgrade now

Already a member?
Log in here (and be sure to check the "remember me" box.)
Login problems? Click here.