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 $802 Econ from $263. – 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: Econ from $280. – 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.…
BOS > Kingston, Jamaica: Econ from $364. – 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 > San Juan, Puerto Rico: Biz from $673 Econ from $85. – 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 > Oranjestad, Aruba: Biz from $960 Econ from $277. – Aug-Oct [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > Willemstad, Curaçao: Biz from $966 Econ from $393. – 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: Econ from $196. – 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 > Punta Cana, Dominican Republic: Econ from $249. – 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 $854 Econ from $257. – 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 $940 Econ from $236. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1061 Econ from $493. – Jan-Mar (Including President’s Day Weekend)
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 $936 Econ from $378. – Dec-Feb
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 $841Econ from $281. – 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 > San Juan, Puerto Rico: Econ from $100. – 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 > Oranjestad, Aruba: Biz from $987 Econ from $291. – Aug-Oct [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $201. – 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.…
BOS > Willemstad, Curaçao: Biz from $993 Econ from $383. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > St. John’s, Antigua And Barbuda: Econ from $464. – Nov-Jan [SOLD OUT]
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
BOS > Montego Bay, Jamaica: Biz from $854 Econ from $275. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1061 Econ from $488. – 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 > San Felipe de Puerto Plata, Dominican Republic: Econ from $367. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Punta Cana, Dominican Republic: Econ from $213. – 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.…
BOS > Piarco, Trinidad and Tobago: Biz from $950 Econ from $441. – 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 $874 Econ from $335. – 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.…
BOS > Willemstad, Curaçao: Biz from $996 Econ from $383. – Jan-Mar
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 $854 Econ from $266. – 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.…
BOS > Grenada, Grenada: Biz from $927 Econ from $307. – 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.…
BOS > San Felipe de Puerto Plata, Dominican Republic: Econ from $370. – Nov-Jan
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 $887 Econ from $225. – 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.…
BOS > Kralendijk, Caribbean Netherlands: Biz from $1108 Econ from $508. – 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 $796 Econ from $196. – 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.…
BOS > George Town, Cayman Islands: Biz from $798 Econ from $345. – 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.…
BOS > San Juan, Puerto Rico: Econ from $120. – 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.…
BOS > Santo Domingo, Dominican Republic: Biz from $720 Econ from $215. – 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.…
BOS > Grenada, Grenada: Biz from $927 Econ from $356. – 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.…
BOS > Willemstad, Curaçao: Biz from $997 Econ from $383. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1070 Econ from $528. – 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.…
BOS > Kingston, Jamaica: Biz from $909. Econ from $298. – 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.…
BOS > George Town, Cayman Islands: Biz from $823 Econ from $375. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…