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

BWI > Simpson Bay, St. Maarten: Biz from $954 Econ from $225. – 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.…

BWI > Christiansted, U.S. Virgin Islands: Biz from $778 Econ from $183. – 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.…

BWI > Saint Thomas Island, U.S. Virgin Islands: Biz from $896 Econ from $164. – 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.…

BWI > San Juan, Puerto Rico: Econ from $118. – 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.…

BWI > Kingston, Jamaica: Biz from $668 Econ from $326. – 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.…

BWI > Piarco, Trinidad and Tobago: Econ from $345. – 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.…

BWI > Montego Bay, Jamaica: Biz from $1009 Econ from $256. – 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.…

BWI > Oranjestad, Aruba: Econ from $251. – Apr-Jun [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

BWI > Port Au Prince, Haiti: Biz from $832 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.…

BWI > San Juan, Puerto Rico: Econ from $108. – 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.…

DCA > Kingston, Jamaica: Biz from $908 Econ from $328. – 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.…

BWI > Montego Bay, Jamaica: Biz from $895 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.…

BWI > Saint Thomas Island, U.S. Virgin Islands: Econ from $175. – 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.…

BWI > Port Au Prince, Haiti: Biz from $857 Econ from $239. – 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.…

BWI > Oranjestad, Aruba: Biz from $786 Econ from $252. – Mar-May [SOLD OUT]
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

BWI > Christiansted, U.S. Virgin Islands: Biz from $986 Econ from $180. – 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.…

BWI > San Juan, Puerto Rico: Econ from $108. – 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.…

BWI > Kingston, Jamaica: Biz from $966 Econ from $124. – Mar-May (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Saint Thomas Island, U.S. Virgin Islands: Econ from $175. – 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.…

BWI > Santo Domingo, Dominican Republic: Econ from $92. – 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.…

IAD > Willemstad, Curaçao: Biz from $1249 Econ from $387. – 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.…

BWI > Christiansted, U.S. Virgin Islands: Biz from $712 Econ from $166. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

DCA > San Juan, Puerto Rico: Econ from $167. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Kingston, Jamaica: Biz from $686 Econ from $327. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Piarco, Trinidad and Tobago: Biz from $1069 Econ from $345. – 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.…

BWI > Simpson Bay, St. Maarten: Econ from $247. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Montego Bay, Jamaica: Biz from $922 Econ from $254. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Kralendijk, Caribbean Netherlands: Biz from $1474 Econ from $400. – Feb-Apr [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Oranjestad, Aruba: Biz from $864 Econ from $213. – Feb-Apr (Including Spring Break) [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

BWI > Saint Thomas Island, U.S. Virgin Islands: Econ from $171. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Christiansted, U.S. Virgin Islands: Biz from $712 Econ from $169. – Feb-Apr [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > San Juan, Puerto Rico: Econ from $116. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > St. John’s, Antigua And Barbuda: Econ from $454. – Mar-May (Including Spring Break) [SOLD OUT]
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…

BWI > Kingston, Jamaica: Biz from $668 Econ from $286. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAD > Piarco, Trinidad and Tobago: Biz from $902 Econ from $357. – Feb-Apr (Including Spring Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Montego Bay, Jamaica: Biz from $910 Econ from $247. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Kralendijk, Caribbean Netherlands: Biz from $1433 Econ from $400. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

BWI > Oranjestad, Aruba: Biz from $836 Econ from $218. – Jan-Mar [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

BWI > Christiansted, U.S. Virgin Islands: Biz from $877 Econ from $186. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…