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 $390. – 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 > Saint Thomas Island, U.S. Virgin Islands: Biz from $742 Econ from $325.- 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 $1119 Econ from $362. – Nov-Jan
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 $919 Econ from $423. – Oct-Dec
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * There only appear to…

IND > Nassau, The Bahamas: Biz from $652 Econ from $309. – 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 > Oranjestad, Aruba: Biz from $1013 Econ from $377. – Jul-Sep (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 > San Juan, Puerto Rico: Biz from $584 Econ from $238. – Oct-Dec
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 $965 Econ from $414. – Dec-Feb
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 $910 Econ from $430. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Piarco, Trinidad and Tobago: Biz from $910 Econ from $498. – 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 > Montego Bay, Jamaica: Biz from $923 Econ from $380. – Dec-Feb (Including MLK Weekend)
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 $1,111 Econ from $331. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Willemstad, Curaçao: Biz from $1,491 Econ from $651. – Feb-Apr
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 $791 Econ from $466. – 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 > Saint Thomas Island, U.S. Virgin Islands: Biz from $811 Econ from $325. – 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.…

IND > Nassau, The Bahamas: Biz from $712 Econ from $312. – 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 > Oranjestad, Aruba: Biz from $1,062 Econ from $421. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IND > San Juan, Puerto Rico: Biz from $628 Econ from $309. – 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 > Simpson Bay, St. Maarten: Biz from $901 Econ from $393. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1,615 Econ from $670. – 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 > Port Royal, The Bahamas: Biz from $823 Econ from $315. – 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 > Providenciales, Turks and Caicos Islands: Econ from $423. – Aug-Oct (Including Labor Day) [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…

IND > Christiansted, U.S. Virgin Islands: Biz from $1,006 Econ from $454. – Oct-Dec
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 $904 Econ from $370. – Jan-Mar
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 $1,122 Econ from $321. – Dec-Feb
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. – 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 > Punta Cana, Dominican Republic: Biz from $937 Econ from $384. – 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 > Nassau, The Bahamas: Biz from $754 Econ from $296. – 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 > Simpson Bay, St. Maarten: Econ from $379. – Oct-Dec
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 $734 Econ from $341. – 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 > Oranjestad, Aruba: Biz from $1,019 Econ from $416. – Jun-Aug (Including Fourth of July and 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 > Oranjestad, Aruba: Econ from $416. – Aug-Oct [SOLD OUT]
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

IND > Port Royal, The Bahamas: Biz from $813 Econ from $329. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1,521 Econ from $651. – 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 $1,124 Econ from $396. – 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 > Montego Bay, Jamaica: Biz from $910 Econ from $360. – 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 > Willemstad, Curaçao: Biz from $1,513 Econ from $673. – Feb-Apr
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, Biz from $826 U.S. Virgin Islands: Econ from $300. – Aug-Oct
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 $914. Econ from $384. – 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.…