Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Christiansted, U.S. Virgin Islands: Biz from $814 Econ from $210. – 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.…
BOS > Grenada, Grenada: Biz from $1127 Econ from $295. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Bridgetown, Barbados: Biz from $996 Econ from $325. – 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.…
BOS > Port Au Prince, Haiti: Biz from $798 Econ from $266. – 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.…
BOS > Willemstad, Curaçao: Biz from $1002 Econ from $384. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Biz from $847 Econ from $203. – 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.…
BOS > San Juan, Puerto Rico: Biz from $625 Econ from $106. – 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.…
BOS > George Town, Cayman Islands: Biz from $1000 Econ from $296. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kralendijk, Caribbean Netherlands: Biz from $1089 Econ from $389. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Simpson Bay, St. Maarten: Biz from $841 Econ from $241. – 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.…
BOS > Oranjestad, Aruba: Biz from $858 Econ from $270. – Oct-Dec [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Piarco, Trinidad and Tobago: Biz from $911 Econ from $217. – 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.…
BOS > Christiansted, U.S. Virgin Islands: Biz from $803 Econ from $225. – 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.…
BOS > Montego Bay, Jamaica: Biz from $894 Econ from $254. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Grenada, Grenada: Econ from $295. – 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.…
BOS > Santo Domingo, Dominican Republic: Biz from $760 Econ from $234. – 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.…
BOS > Kingston, Jamaica: Biz from $924 Econ from $298. – 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.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Biz from $734 Econ from $207. – 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.…
BOS > San Juan, Puerto Rico: Econ from $98. – 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.…
BOS > Simpson Bay, St. Maarten: Biz from $827 Econ from $252. – 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.…
BOS > Montego Bay, Jamaica: Biz from $884 Econ from $258. – 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.…
BOS > Willemstad, Curaçao: Biz from $1010 Econ from $374. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Grenada, Grenada: Biz from $894 Econ from $285. – Oct-Dec (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.…
BOS > Oranjestad, Aruba: Biz from $966 Econ from $254. – Jul-Sep [SOLD OUT]
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
BOS > Kralendijk, Caribbean Netherlands: Econ from $360. – 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.…
BOS > Kingston, Jamaica: Biz from $938 Econ from $338. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > George Town, Cayman Islands: Biz from $930. Econ from $324. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Biz from $718 Econ from $195. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Juan, Puerto Rico: Biz from $645 Econ from $106. – 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.…
BOS > Simpson Bay, St. Maarten: Biz from $823 Econ from $256. – 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.…
BOS > Montego Bay, Jamaica: Biz from $864 Econ from $342. – 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.…
BOS > Willemstad, Curaçao: Biz from $1056 Econ from $354. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Bridgetown, Barbados: Biz from $970 Econ from $207. – 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.…
BOS > George Town, Cayman Islands: Biz from $948 Econ from $364. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kralendijk, Caribbean Netherlands: Biz from $1188 Econ from $528. – 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.…
BOS > Grenada, Grenada: Biz from $1001 Econ from $265. – 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.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Biz from $718 Econ from $211. – 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.…
BOS > San Juan, Puerto Rico: Econ from $72. – 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.…
BOS > Montego Bay, Jamaica: Biz from $864 Econ from $270. – 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.…