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)
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.…

IND > Providenciales, Turks and Caicos Islands: Biz from $831 Econ from $341. – Apr-Jun [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…

IND > Oranjestad, Aruba: Biz from $1,109 Econ from $456. – 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 > Santo Domingo, Dominican Republic: Biz from $833 Econ from $385. – 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 > Montego Bay, Jamaica: Biz from $932 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 > Christiansted, U.S. Virgin Islands: Biz from $900 Econ from $300. – 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 > San Juan, Puerto Rico: Biz from $708 Econ from $245. – 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 $977 Econ from $317. – 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 $689 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 > Oranjestad, Aruba: Biz from $1041 Econ from $451.- Apr-Jun (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…

IND > Providenciales, Turks and Caicos Islands: Biz from $856 Econ from $321. – Aug-Oct [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…

Denver to Roatan: My Best Trip Ever. $854 including 7 nights [SOLD OUT]
First off – Roatan is never cheap to get to. Flights alone are usually over $800 (Trust me- I’ve been watching for years.) Years ago, I had a “buddy pass” from a very generous pilot friend & decided to head out of town when my kids were on vacation with their Mom. Since I had to fly […]

Denver to Roatan: My Best Trip Ever. $854 including 7 nights [SOLD OUT]
First off – Roatan is never cheap to get to. Flights alone are usually over $800 (Trust me- I’ve been watching for years.) Years ago, I had a “buddy pass” from a very generous pilot friend & decided to head out of town when my kids were on vacation with their Mom. Since I had to fly […]
