IND > Montego Bay, Jamaica: Flight & 6 nights: $586 – 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:

IND> George Town, Cayman Islands: Flight & 7 nights: $1,004 – Feb-Apr

IND > George Town, Cayman Islands: Flight & 7 nights: $1,004 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

IND> Providenciales, Turks and Caicos Islands: Flight & 6 nights: $867 – Dec-Feb

IND > Providenciales, Turks and Caicos Islands: Flight & 6 nights: $867 – Dec-Feb

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


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

IND > San Juan, Puerto Rico: Flight & 6 nights: $551 – Oct-Dec

* This is a “fare dump” with a few alternate dates available. Indianapolis to San Juan, Puerto Rico: 6 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:

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $717 – 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:

IND> George Town, Cayman Islands: Flight & 10 nights: $1,232

IND > George Town, Cayman Islands: Flight & 10 nights: $1,232 – 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:

IND > Montego Bay, Jamaica: Flight & 6 nights: $645 – 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…...


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IND> Honolulu, Hawaii: Flight & 10 nights: $1,117 – Dec-Feb

IND > Honolulu, Hawaii: Flight & 10 nights: $1,117 – 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:

IND> Providenciales, Turks and Caicos Islands: Flight & 6 nights: $937 – Jan-Mar

IND > Providenciales, Turks and Caicos Islands: Flight & 6 nights: $937 – Jan-Mar

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


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

IND> San Juan, Puerto Rico: Flight & 8 nights: $518 – Sep-Nov (Including Fall Break)

IND > San Juan, Puerto Rico: Flight & 8 nights: $518 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

IND> George Town, Cayman Islands: Flight & 6 nights: $850 – Jan-Mar

IND > George Town, Cayman Islands: Flight & 6 nights: $850 – 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:

– Nov-Jan IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $790

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $790 – 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:

IND> San Juan, Puerto Rico: Flight & 5 nights: $430 – Sep-Nov (Including Fall Break)

IND > San Juan, Puerto Rico: Flight & 5 nights: $430 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $975 – Oct-Dec

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $975 – Oct-Dec

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

IND> Providenciales, Turks and Caicos Islands: Flight & 7 nights: $1,029 – Dec-Feb (Including Winter Break)

IND > Providenciales, Turks and Caicos Islands: Flight & 7 nights: $1,029 – Dec-Feb (Including Winter Break)

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


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

IND > Larnaca, Cyprus: Flight & 5 nights: $663 – 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:

– Feb-Apr (Including Spring Break) IND> George Town, Cayman Islands: Flight & 7 nights: $954

IND > George Town, Cayman Islands: Flight & 7 nights: $954 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

IND > Aguadilla, Puerto Rico: Flight & 12 nights: $1,290 – Sep-Nov

* This is a “fare dump” with a few alternate dates available. Indianapolis to Aguadilla, Puerto Rico: 12 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:

IND> Kahului, Hawaii: Flight & 5 nights: $758 – Aug-Oct

IND > Kahului, Hawaii: Flight & 5 nights: $758 – 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:

– Nov-Jan (Including Winter Break) IND> Nassau, The Bahamas: Flight & 4 nights: $627

IND > Nassau, The Bahamas: Flight & 4 nights: $627 – Nov-Jan (Including Winter Break)

* This is a “fare dump” with a few alternate dates available. Indianapolis to Nassau, The Bahamas: 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:

IND> San Juan, Puerto Rico: Flight & 5 nights: $457 – Aug-Oct

IND > San Juan, Puerto Rico: Flight & 5 nights: $457 – Aug-Oct

* This is a “fare dump” with a few alternate dates available. Indianapolis to San Juan, Puerto Rico: 5 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:

IND> Kahului, Hawaii: Flight & 7 nights: $861 – Aug-Oct

IND > Kahului, Hawaii: Flight & 7 nights: $861 – 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:

IND> Montego Bay, Jamaica: Flight & 3 nights: $579 – Sep-Nov

IND > Montego Bay, Jamaica: Flight & 3 nights: $579 – Sep-Nov

* 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:

IND> Male, Maldives: Flight & 7 nights: $1,459 – Oct-Dec

IND > Male, Maldives: Flight & 7 nights: $1,459 – 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:

IND> Aguadilla, Puerto Rico: Flight & 9 nights: $874 – Aug-Oct

IND > Aguadilla, Puerto Rico: Flight & 9 nights: $874 – 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:

IND> George Town, Cayman Islands: Flight & 5 nights: $940 – Dec-Feb

IND > George Town, Cayman Islands: Flight & 5 nights: $940 – 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:

IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $743 – Jan-Mar

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 6 nights: $743 – 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:

IND> Kailua Kona, Hawaii: Flight & 4 nights: $656 – Aug-Oct

IND > Kailua Kona, Hawaii: Flight & 4 nights: $656 – 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:

IND> Providenciales, Turks and Caicos Islands: Flight & 5 nights: $883 – Nov-Jan

IND > Providenciales, Turks and Caicos Islands: Flight & 5 nights: $883 – Nov-Jan

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:

IND> Kahului, Hawaii: Flight & 4 nights: $806 – Oct-Dec

IND > Kahului, Hawaii: Flight & 4 nights: $806 – Oct-Dec

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:

IND> San Juan, Puerto Rico: Flight & 14 nights: $902 – Sep-Nov (Including Fall Break)

IND > San Juan, Puerto Rico: Flight & 14 nights: $902 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

– Feb-Apr (Including Spring Break) IND> George Town, Cayman Islands: Flight & 14 nights: $1,405

IND > George Town, Cayman Islands: Flight & 14 nights: $1,405 – 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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You'll get trip alerts 3 days before tens of thousands of free subscribers, and they'll look like this:

IND> Aguadilla, Puerto Rico: Flight & 7 nights: $867 – Aug-Oct

IND > Aguadilla, Puerto Rico: Flight & 7 nights: $867 – 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:

IND> Honolulu, Hawaii: Flight & 8 nights: $862 – Sep-Nov

IND > Honolulu, Hawaii: Flight & 8 nights: $862 – 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:

IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $832 – Dec-Feb

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $832 – Dec-Feb

* 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:

IND> Kailua Kona, Hawaii: Flight & 8 nights: $830 – Aug-Oct

IND > Kailua Kona, Hawaii: Flight & 8 nights: $906- 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:

IND> Kahului, Hawaii: Flight & 8 nights: $986 – Oct-Dec

IND > Kahului, Hawaii: Flight & 8 nights: $986 – 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:

IND> Montego Bay, Jamaica: Flight & 8 nights: $642 – Aug-Oct

IND > Montego Bay, Jamaica: Flight & 8 nights: $642 – 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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IND> Christiansted, U.S. Virgin Islands: Flight & 5 nights: $961 – Sep-Nov

IND > Christiansted, U.S. Virgin Islands: Flight & 5 nights: $961 – Sep-Nov

* This is a “fare dump” with a few alternate dates available. Indianapolis to Christiansted, U.S. Virgin Islands: 5 night…...


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IND> Lihue, Hawaii: Flight & 5 nights: $923 – Aug-Oct

IND > Lihue, Hawaii: Flight & 5 nights: $923 – Aug-Oct

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


Details to this trip are for premium members only.

Members:
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Non-Members:
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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.

Tired of searching for these trips yourself?
Read our FAQ page to see if "The JGOOT Way" is a fit for you. If so, Upgrade to a premium account

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