* There only appear to be a few seats at this price and availability is spotty. It will take a…
BOS > Boracay, Philippines: Econ from $917. – Oct-Dec [SOLD OUT]
Have I mentioned that the Philippines has some of the best diving in the world? The beaches are amazing too.…
BOS > Kralendijk, Caribbean Netherlands: Biz from $1623. Econ from $367. – 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 > Praia, Cape Verde: Econ from $592.- Oct-Dec (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > George Town, Cayman Islands: Biz from $957 Econ from $270.- 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 > Barcelona, Spain: Econ from $328. – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Recife, Brazil: Econ from $553. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Nadi, Fiji: Econ from $835. – Apr-Jun (Including Summer Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Miami, Florida: Biz from $235 Econ from $92. – 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 > Managua, Nicaragua: Biz from $873 Econ from $299. – Nov-Jan (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 > Bridgetown, Barbados: Econ from $315. – 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 > Providenciales, Turks and Caicos Islands: Biz from $892 Econ from $329. – Sep-Nov (Including Fall Break) [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…
BOS > Thera, Greece: Econ from $594. – Nov-Jan
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
BOS > Fort Lauderdale, Florida: Biz from $243 Econ from $74. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
BOS > Cancun, Mexico: Biz from $565 Econ from $265. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > West Palm Beach, Florida: Econ from $137. – Oct-Dec [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Dubai, United Arab Emirates: Econ from $618. – Oct-Dec (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 > Belize City, Belize: Biz from $571 Econ from $332.- Nov-Jan
* There only appear to be a few seats at this price and availability is spotty. It will take a…
BOS > Panama City, Panama: Biz from $1183 Econ from $300.- 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 $550 Econ from $236.- Nov-Jan
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 $1151 Econ from $429. – 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 > Montego Bay, Jamaica: Biz from $582 Econ from $261. – 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 > Georgetown, Guyana: Biz from $1302 Econ from $437. – 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 > Coxen Hole, Honduras: Biz from $1218 Econ from $335. – Sep-Nov (Including Fall Break) [SOLD OUT]
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
BOS > Male, Maldives: Econ from $909. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Oranjestad, Aruba: Biz from $632 Econ from $322. – Sep-Nov [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > Myrtle Beach, South Carolina: Biz from $348 Econ from $137. – Sep-Nov [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Liberia, Costa Rica: Biz from $1231 Econ from $342.- Oct-Dec [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 > Luqa, Malta: Econ from $417.- Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Willemstad, Curaçao: Biz from $1199 Econ from $308.- 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 > Riga, Latvia: Econ from $347.- Oct-Dec (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > George Town, Cayman Islands: Biz from $884 Econ from $270. – 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 > Los Angeles, California: Biz from $502 Econ from $156. – Oct-Dec [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
BOS > Split, Croatia: Econ from $371. – 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 > San Juan, Puerto Rico: Biz from $411 Econ from $176. – Feb-Apr
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 $397 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 > Nadi, Fiji: Econ from $820. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Miami, Florida: Biz from $233 Econ from $58. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Managua, Nicaragua: Biz from $823 Econ from $283. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Palanga, Lithuania: Econ from $406. – 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…