Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Rabat, Morocco: Econ from $431. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Jacksonville, Florida: Biz from $407 Econ from $127.- Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Oranjestad, Aruba: Biz from $497 Econ from $306.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Larnaca, Cyprus: Econ from $520.- Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Liberia, Costa Rica: Biz from $983 Econ from $290.- Jan-Mar
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
BOS > West Palm Beach, Florida: Econ from $137. – Oct-Dec [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Male, Maldives: Econ from $822. – Jan-Mar (Presidents day Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Myrtle Beach, South Carolina: Biz from $377. Econ from $107. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Willemstad, Curaçao: Biz from $870. Econ from $344. – 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 > San Juan, Puerto Rico: Biz from $462 Econ from $175. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Abu Dhabi, United Arab Emirates: Econ from $683. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Belize City, Belize: Biz from $933. Econ from $328. – Nov-Jan
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
BOS > Coxen Hole, Honduras: Biz from $1132 Econ from $342. – Jan-Mar
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
BOS > Managua, Nicaragua: Biz from $606 Econ from $317. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Miami, Florida: Biz from $240 Econ from $107. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Los Angeles, California: Econ from $128. – Nov-Jan
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
BOS > Chennai, India: Econ from $744. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Punta Cana, Dominican Republic: Biz from $481. Econ from $284. – 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 > Barcelona, Spain: Econ from $326.- Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > George Town, Cayman Islands: Biz from $1045 Econ from $270.- 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 > Lisbon, Portugal: Econ from $371. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Fort Lauderdale, Florida: Biz from $266 Econ from $86. – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > San Salvador, El Salvador: Biz from $721 Econ from $254. – 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 $399. – Jan-Mar
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
BOS > Riga, Latvia: Econ from $394. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Guatemala City, Guatemala: Biz from $529 Econ from $203. – 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 Jose, Costa Rica: Biz from $520 Econ from $206. – 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 > Malaga, Spain: Econ from $357.- Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Panama City, Panama: Biz from $1072 Econ from $448.- Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > San Pedro Sula, Honduras: Biz from $620 Econ from $280.- Nov-Jan
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 $483 Econ from $243. – 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 > Jacksonville, Florida: Biz from $447 Econ from $117. – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Split, Croatia: Econ from $365. – Oct-Dec [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
BOS > Oranjestad, Aruba: Biz from $968 Econ from $336. – Sep-Nov (Including Fall Break) [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Luqa, Malta: Econ from $426. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Myrtle Beach, South Carolina: Biz from $333 Econ from $153. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Larnaca, Cyprus: Econ from $506.- Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Liberia, Costa Rica: Biz from $1149 Econ from $333.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
BOS > Willemstad, Curaçao: Biz from $887 Econ from $373. – 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.…