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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(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…...


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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…...


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IND > Providenciales, Turks and Caicos Islands: Flight & 5 nights: $779 – 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> San Juan, Puerto Rico: Flight & 6 nights: $1,023 – Dec-Feb (Including Winter Break)

IND > San Juan, Puerto Rico: Flight & 6 nights: $1,023 – Dec-Feb (Including Winter Break)

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


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IND > Piarco, Trinidad and Tobago: Flight & 4 nights: $654 – Oct-Dec (Including Thanksgiving)

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


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IND> Saint Thomas Island, U.S. Virgin Islands: Flight & 3 nights: $695 – Nov-Jan

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 3 nights: $695 – Nov-Jan

* 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 & 7 nights: $625 – Dec-Feb

IND > Montego Bay, Jamaica: Flight & 7 nights: $625 – 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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– Jan-Mar (Including President’s Day Weekend) IND> George Town, Cayman Islands: Flight & 4 nights: $848

IND > George Town, Cayman Islands: Flight & 4 nights: $848 – 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 > Providenciales, Turks and Caicos Islands: Flight & 7 nights: $1,073 – Jan-Mar (Including President’s Day Weekend)

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


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IND > Kralendijk, Caribbean Netherlands: Flight & 7 nights: $991 – 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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IND> San Juan, Puerto Rico: Flight & 6 nights: $623 – Jan-Mar

IND > San Juan, Puerto Rico: Flight & 6 nights: $623 – 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> Saint Thomas Island, U.S. Virgin Islands: Flight & 8 nights: $1,132 – Dec-Feb (Including Winter Break)

IND > Saint Thomas Island, U.S. Virgin Islands: Flight & 8 nights: $1,132 – Dec-Feb (Including Winter Break)

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


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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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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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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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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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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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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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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> 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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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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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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– 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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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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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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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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– 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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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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– 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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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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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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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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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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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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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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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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