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

IND > San Juan, Puerto Rico: Econ from $296. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $905 Econ from $360. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Simpson Bay, St. Maarten: Econ from $325. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Biz from $926 Econ from $306. – Oct-Dec (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $1,521 Econ from $766. – May-Jul (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.…

IND > Bridgetown, Barbados: Econ from $482. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $742 Econ from $300. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Nassau, The Bahamas: Biz from $710 Econ from $400. – May-Jul (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.…

IND > San Juan, Puerto Rico: Biz from $496 Econ from $238. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Biz from $1,007 Econ from $407. – May-Jul (Including Summer Break) [SOLD OUT]
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

IND > Willemstad, Curaçao: Econ from $521. – May-Jul (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.…

IND > Montego Bay, Jamaica: Biz from $928 Econ from $352. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Simpson Bay, St. Maarten: Econ from $427. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Biz from $1,002 Econ from $457. – Oct-Dec (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Christiansted, U.S. Virgin Islands: Biz from $1,135 Econ from $464. – 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.…

IND > Providenciales, Turks and Caicos Islands: Biz from $921 Econ from $461. – Jun-Aug (Including Summer Break) [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is a “fare…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $1,001 Econ from $362. – Jun-Aug (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.…

IND > San Juan, Puerto Rico: Biz from $756 Econ from $194. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Nassau, The Bahamas: Biz from $710 Econ from $378. – Apr-Jun (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.…

IND > Oranjestad, Aruba: Biz from $1,042 Econ from $391. – Apr-Jun [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

IND > Willemstad, Curaçao: Econ from $618. – May-Jul (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.…

IND > Kingston, Jamaica: Biz from $1,129 Econ from $491. – Apr-Jun (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.…

IND > Santiago de los Caballeros, Dominican Republic: Biz from $946 Econ from $379. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Econ from $461. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Santiago de los Caballeros, Dominican Republic: Biz from $911 Econ from $352. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Punta Cana, Dominican Republic: Biz from $548 Econ from $311. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $619 Econ from $300. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $462 Econ from $186. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $1,358 Econ from $670. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Simpson Bay, St. Maarten: Biz from $579 Econ from $276. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Econ from $441. – Jun-Aug (Including Summer Break) [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IND > Kingston, Jamaica: Econ from $485. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $960 Econ from $352. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Christiansted, U.S. Virgin Islands: Biz from $756 Econ from $260. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $549 Econ from $196. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $638 Econ from $280. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Biz from $1,238 Econ from $481. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $1,301 Econ from $646. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Simpson Bay, St. Maarten: Biz from $637 Econ from $300. – Mar-May [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
