SFO> Willemstad, Curaçao: Flight & 8 nights: $978 – Dec-Feb

SFO > Willemstad, Curaçao: Flight & 8 nights: $978 – 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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SFO > George Town, Cayman Islands: Flight & 4 nights: $1,205 – Nov-Jan (Including Winter Break)

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


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OAK> San Juan, Puerto Rico: Flight & 4 nights: $582 – Dec-Feb (Including MLK Weekend)

OAK > San Juan, Puerto Rico: Flight & 4 nights: $582 – 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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OAK > Montego Bay, Jamaica: Flight & 9 nights: $801 – Dec-Feb (Including MLK Weekend)

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


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SFO> George Town, Cayman Islands: Flight & 7 nights: $901 – Jan-Mar

SFO > George Town, Cayman Islands: Flight & 7 nights: $901 – 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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SFO> Piarco, Trinidad and Tobago: Flight & 8 nights: $690 – Jan-Mar

SFO > Piarco, Trinidad and Tobago: Flight & 8 nights: $690 – 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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SFO > Willemstad, Curaçao: Flight & 8 nights: $659 – 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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SFO> St. John’s, Antigua And Barbuda: Flight & 3 nights: $670 – Jan-Mar (Including President’s Day Weekend)

SFO > St. John’s, Antigua And Barbuda: Flight & 3 nights: $670 – Jan-Mar (Including President’s Day Weekend)

The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…...


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SFO > Oranjestad, Aruba: Flight & 7 nights: $718 – Feb-Apr

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


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OAK> San Juan, Puerto Rico: Flight & 10 nights: $865 – Dec-Feb

OAK > San Juan, Puerto Rico: Flight & 10 nights: $865 – 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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SFO> Montego Bay, Jamaica: Flight & 8 nights: $638 – Nov-Jan

SFO > Montego Bay, Jamaica: Flight & 8 nights: $638 – 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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SJC> Saint Thomas Island, U.S. Virgin Islands: Flight & 5 nights: $629 – Nov-Jan

SJC > Saint Thomas Island, U.S. Virgin Islands: Flight & 5 nights: $629 – Nov-Jan

* This is a “fare dump” with a few alternate dates available. San Jose to Saint Thomas Island, U.S. Virgin…...


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SJC> George Town, Cayman Islands: Flight & 7 nights: $840- Dec-Feb

SJC > George Town, Cayman Islands: Flight & 7 nights: $840- 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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SFO> Kingston, Jamaica: Flight & 4 nights: $566 – Apr-Jun

SFO > Kingston, Jamaica: Flight & 4 nights: $566 – 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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SFO> Willemstad, Curaçao: Flight & 9 nights: $1,286 – Oct-Dec (Including Thanksgiving)

SFO > Willemstad, Curaçao: Flight & 9 nights: $1,286 – Oct-Dec (Including Thanksgiving)

* 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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SFO> Hamilton, Bermuda: Flight & 9 nights: $1,284 – Sep-Nov (Including Fall Break)

SFO > Hamilton, Bermuda: Flight & 9 nights: $1,284 – Sep-Nov (Including Fall Break)

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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SFO> St. John’s, Antigua and Barbuda: Flight & 9 nights: $911 – Dec-Feb (Including MLK Weekend)

SFO > St. John’s, Antigua and Barbuda: Flight & 9 nights: $911 – Dec-Feb (Including MLK Weekend)

The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…...


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SFO> Montego Bay, Jamaica: Flight & 8 nights: $655 – Nov-Jan

SFO > Montego Bay, Jamaica: Flight & 8 nights: $655 – 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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SFO> George Town, Cayman Islands: Flight & 7 nights: $896 – May-Jul

SFO > George Town, Cayman Islands: Flight & 7 nights: $896 – May-Jul

* This is a “fare dump” with a few alternate dates available. San Francisco to George Town, Cayman Islands: 7…...


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LAX> Willemstad, Curaçao: Flight & 7 nights: $628 – Nov-Jan

LAX > Willemstad, Curaçao: Flight & 7 nights: $628 – 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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SFO > Willemstad, Curaçao: Flight & 6 nights: $693 – 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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SFO> Ponce, Puerto Rico: Flight & 6 nights: $578 – Feb-Apr (Including Spring Break)

SFO > Ponce, Puerto Rico: Flight & 6 nights: $578 – Feb-Apr (Including Spring Break)

* This is a “fare dump” with a few alternate dates available. San Francisco to Ponce, Puerto Rico: 6 night…...


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SFO> Kingston, Jamaica: Flight & 4 nights: $527 – Nov-Jan

SFO > Kingston, Jamaica: Flight & 4 nights: $527 – 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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SFO > Aguadilla, Puerto Rico: Flight & 10 nights: $748 – 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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SFO > Piarco, Trinidad and Tobago: Flight & 7 nights: $588 – 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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OAK> George Town, Cayman Islands: Flight & 10 nights: $1,782 – Jan-Mar (Including President’s Day Weekend)

OAK > George Town, Cayman Islands: Flight & 10 nights: $1,782 – Jan-Mar (Including President’s Day Weekend)

* This is a “fare dump” with a few alternate dates available. Oakland to George Town, Cayman Islands: 10 night…...


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SFO> Saint Thomas Island, U.S. Virgin Islands: Flight & 10 nights: $930 – Feb-Apr

SFO > Saint Thomas Island, U.S. Virgin Islands: Flight & 10 nights: $930 – Feb-Apr

* This is a “fare dump” with a few alternate dates available. San Francisco to Saint Thomas Island, U.S. Virgin…...


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SFO> Aguadilla, Puerto Rico: Flight & 3 nights: $460 – Nov-Jan

SFO > Aguadilla, Puerto Rico: Flight & 3 nights: $460 – 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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SFO> Willemstad, Curaçao: Flight & 11 nights: $1,171 – May-Jul (Including Summer Break)

SFO > Willemstad, Curaçao: Flight & 11 nights: $1,171 – 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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SFO > George Town, Cayman Islands: Flight & 3 nights: $530 – 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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SFO> Ponce, Puerto Rico: Flight & 3 nights: $515- Jan-Mar

SFO > Ponce, Puerto Rico: Flight & 3 nights: $515- 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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SJC > Saint Thomas Island, U.S. Virgin Islands: Flight & 4 nights: $696 – Nov-Jan

* This is a “fare dump” with a few alternate dates available. San Jose to Saint Thomas Island, U.S. Virgin…...


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SFO > Willemstad, Curaçao: Flight & 9 nights: $857 – 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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SJC> San Juan, Puerto Rico: Flight & 8 nights: $697

SJC > San Juan, Puerto Rico: Flight & 8 nights: $697 – Aug-Oct

* This is a “fare dump” with a few alternate dates available. San Jose to San Juan, Puerto Rico: 8…...


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SFO > Piarco, Trinidad and Tobago: Flight & 7 nights: $633 – 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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