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

BOS > Nassau, The Bahamas: Biz from $636 Econ from $246. – 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.…

BOS > San Juan, Puerto Rico: Econ from $163. – 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 > Aguadilla, Puerto Rico: Econ from $210. – 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.…

BOS > Port Au Prince, Haiti: Biz from $832. Econ from $261. – 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.…

BOS > Willemstad, Curaçao: Biz from $1043 Econ from $433. – 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 > Ponce, Puerto Rico: Econ from $134. – 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.…

BOS > Providenciales, Turks and Caicos Islands: Biz from $907. Econ from $383. – Mar-May (Including Spring Break) [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. (Pictures included) * This is…

BOS > Piarco, Trinidad and Tobago: Biz from $799. Econ from $337. [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 $750. Econ from $275. – 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.…

BOS > Montego Bay, Jamaica: Biz from $872. Econ from $258. – 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.…

BOS > Nassau, The Bahamas: Econ from $290. – 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.…

BOS > Santo Domingo, Dominican Republic: Biz from $720. Econ from $238. – 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.…

BOS > Oranjestad, Aruba: Biz from $891. Econ from $222. – Jan-Mar [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

BOS > Punta Cana, Dominican Republic: Econ from $248.- 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.…

BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $193. – 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.…

BOS > Port Au Prince, Haiti: Biz from $932. Econ from $243. – 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.…

BOS > Willemstad, Curaçao: Biz from $1045 Econ from $372. – 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 > Christiansted, U.S. Virgin Islands: Biz from $819. Econ from $184. – 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.…

BOS > Providenciales, Turks and Caicos Islands: Biz from $868. Econ from $365. – Mar-May (Including Spring Break) [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is a “fare…

BOS > San Juan, Puerto Rico: Econ from $115. – 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.…

BOS > Ponce, Puerto Rico: Econ from $166. – 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.…

BOS > Kralendijk, Caribbean Netherlands: Biz from $1144. Econ from $403. – 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.…

BOS > Simpson Bay, St. Maarten: Econ from $257. – 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.…

BOS > Montego Bay, Jamaica: Biz from $829. Econ from $260. – Dec-Feb [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 $782. Econ from $264. – 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.…

BOS > Kingston, Jamaica: Biz from $688. Econ from $295. – 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.…

BOS > Nassau, The Bahamas: Biz from $826. Econ from $303. – 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.…

BOS > Ponce, Puerto Rico: Econ from $115. – 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.…

BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $191. – Dec-Feb [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 $893. Econ from $228. – Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

BOS > Santiago de los Caballeros, Dominican Republic: Biz from $643. Econ from $252. – 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.…

BOS > Christiansted, U.S. Virgin Islands: Biz from $840. Econ from $188.- 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.…

BOS > Punta Cana, Dominican Republic: 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.…

BOS > San Juan, Puerto Rico: Econ from $115. – 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.…

BOS > Montego Bay, Jamaica: Biz from $827. Econ from $258. – 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.…

BOS > George Town, Cayman Islands: Biz from $810. Econ from $262. – 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.…

BOS > Port Au Prince, Haiti: Biz from $780. Econ from $245. – Dec-Feb [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: Econ from $249. – Dec-Feb [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 $686 Econ from $297. – 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.…