Caribbean – Page 18 – JGOOT

SJC > George Town, Cayman Islands: From $303 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SJC > Kralendijk, Caribbean Netherlands: From $462 round-trip – Oct-Dec *BB [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Willemstad, Curaçao: From $430 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

OAK > Saint Thomas Island, U.S. Virgin Islands: From $260 round-trip – Jul-Sep (Including Summer Break)

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Santo Domingo, Dominican Republic: From $250 round-trip – Aug-Oct *BB [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Grenada, Grenada: From $286 round-trip – Oct-Dec *BB [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > San Juan, Puerto Rico: From $248 round-trip – Jul-Sep (Including Summer Break) *BB

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Piarco, Trinidad and Tobago: From $457 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Piarco, Trinidad and Tobago: From $438 round-trip – Sep-Nov [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

OAK > Montego Bay, Jamaica: From $335 round-trip – Jul-Sep (Including Summer Break)

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

OAK > Kingston, Jamaica: From $311 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Santo Domingo, Dominican Republic: From $254 round-trip – Dec-Feb [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Willemstad, Curaçao: From $430 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > San Juan, Puerto Rico: From $252 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Saint Thomas Island, U.S. Virgin Islands: From $387 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

SFO > Kralendijk, Caribbean Netherlands: From $565 round-trip – Nov-Jan [SOLD OUT]

Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

OAK > Oranjestad, Aruba: From $315 round-trip – Jun-Aug (Including Summer Break)

When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

SFO > Santo Domingo, Dominican Republic: From $256 round-trip – Jun-Aug (Including Summer Break)

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

SFO > Willemstad, Curaçao: From $414 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

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

OAK > San Juan, Puerto Rico: From $256 round-trip – Jun-Aug (Including Summer Break)

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

SFO > Christiansted, U.S. Virgin Islands: From $299 round-trip – Jul-Sep [SOLD OUT]

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

SFO > Saint Thomas Island, U.S. Virgin Islands: From $334 round-trip – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]

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

SFO > Willemstad, Curaçao: From $430 round-trip – May-Jul (Including Summer Break) [SOLD OUT]

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

SFO > Santo Domingo, Dominican Republic: From $254 round-trip – Nov-Jan [SOLD OUT]

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

OAK > San Juan, Puerto Rico: From $208 round-trip – Jun-Aug (Including Summer Break)

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

SFO > Kralendijk, Caribbean Netherlands: From $566 round-trip – Nov-Jan [SOLD OUT]

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

SFO > Oranjestad, Aruba: From $371 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]

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

SFO > Saint Thomas Island, U.S. Virgin Islands: From $351 round-trip – Jul-Sep [SOLD OUT]

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

SFO > Santo Domingo, Dominican Republic: From $254 round-trip – Dec-Feb [SOLD OUT]

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

SFO > Willemstad, Curaçao: From $399 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

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

OAK > San Juan, Puerto Rico: From $239 round-trip – Jul-Sep [SOLD OUT]

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

OAK > Punta Cana, Dominican Republic: From $266 round-trip – May-Jul (Including Summer Break) [SOLD OUT]

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

SFO > Saint Thomas Island, U.S. Virgin Islands: From $351 round-trip – Aug-Oct [SOLD OUT]

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

SFO > Santo Domingo, Dominican Republic: From $245 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]

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

OAK > George Town, Cayman Islands: From $438 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]

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

OAK > San Juan, Puerto Rico: From $65 round-trip – May-Jul (Including Summer Break) [SOLD OUT]

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

SFO > Piarco, Trinidad and Tobago: From $251 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]

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

SFO > Christiansted, U.S. Virgin Islands: From $249 round-trip – May-Jul (Including Summer Break) [SOLD OUT]

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

OAK > Oranjestad, Aruba: From $194 round-trip – May-Jul (Including Summer Break) [SOLD OUT]

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

OAK > Punta Cana, Dominican Republic: From $193 round-trip [SOLD OUT]

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