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 $795 Econ from $351. – Mar-May
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. (Pictures included) * This is…
BOS > Oranjestad, Aruba: Biz from $523. Econ from $235. – Feb-Apr (Including Spring Break)
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Kingston, Jamaica: Biz from $825 Econ from $424. – May-Jul (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 > Willemstad, Curaçao: Biz from $971 Econ from $275.- 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 > George Town, Cayman Islands: Biz from $504 Econ from $279. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1292. Econ from $452. – Apr-Jun
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 $531. Econ from $273. – Feb-Apr
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 $584. Econ from $256. – Feb-Apr
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 $982. Econ from $296. – 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 > San Juan, Puerto Rico: Biz from $461. Econ from $151. – Mar-May
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 $767. Econ from $358. – 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 > Willemstad, Curaçao: Biz from $931. Econ from $278. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Santiago de los Caballeros, Dominican Republic: Biz from $486. Econ from $261. – Jan-Mar (Presidents day Weekend)
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 $646. Econ from $299. – Feb-Apr
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 $786. Econ from $201. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
BOS > Santo Domingo, Dominican Republic: Biz from $522 Econ from $235. – 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 $692. Econ from $290. – Jan-Mar
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: Econ from $473. – Jan-Mar
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 $1000. Econ from $316. – 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 > Santo Domingo, Dominican Republic: Biz from $559 Econ from $262. – Jan-Mar
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 $857 Econ from $291. – 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 > Grenada, Grenada: Biz from $879. Econ from $399. – 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 > Punta Cana, Dominican Republic: Biz from $486 Econ from $254. – 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 > Heraklion, Greece: Econ from $551. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Kingston, Jamaica: Biz from $845 Econ from $360. – 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 > Piarco, Trinidad and Tobago: Biz from $600 Econ from $266. – 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 $464. Econ from $270. – Jan-Mar
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 $1442. Econ from $432. – Apr-Jun
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 $470. 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 > Bridgetown, Barbados: Biz from $979. 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 > Willemstad, Curaçao: Biz from $783 Econ from $244.- 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 $620. Econ from $354. – 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 > Christiansted, U.S. Virgin Islands: Biz from $474 Econ from $217. – 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: Biz from $339. Econ from $119. – Jan-Mar
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 $591. Econ from $239. – 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 > Piarco, Trinidad and Tobago: Biz from $595. Econ from $235. – Feb-Apr
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 $946. Econ from $279. – 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 > Kralendijk, Caribbean Netherlands: Biz from $1274. Econ from $402. – 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 $559 Econ from $262. – Jan-Mar [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…