Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Praia, Cape Verde: Biz from $1741 Econ from $584. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Casablanca, Morocco: Econ from $381. – Mar-May (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Charlottesville, Virginia: Econ from $159. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Fort Lauderdale, Florida: Biz from $259 Econ from $84. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Baku, Azerbaijan: Econ from $701. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Poznan, Poland: Econ from $362. – Mar-May
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
BOS > Faro, Portugal: Biz from $1331. Econ from $376. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Cartagena, Colombia: Biz from $625. Econ from $265. – 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 > Charleston, South Carolina: Econ from $176. – May-Jul (Including Summer Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Miami, Florida: Biz from $239. Econ from $71. – Feb-Apr (Including Spring Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Dubai, United Arab Emirates: Econ from $571. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Pittsburgh, Pennsylvania: Biz from $292. Econ from $136. – Feb-Apr (Including Spring Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Athens, Greece: Econ from $470. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Charlotte, North Carolina: Biz from $392. Econ from $107. – May-Jul (Including Summer Break)
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 $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 > Algiers, Algeria: Econ from $393. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > San Antonio, Texas: Econ from $178. – Feb-Apr (Including Spring Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Denver, Colorado: Econ from $142. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Sofia, Bulgaria: Econ from $336. – Mar-May
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
BOS > Belgrade, Serbia: Econ from $366. – 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 > Marrakesh, Morocco: Econ from $519.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Detroit, Michigan: Biz from $308 Econ from $102.- Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Sibiu, Romania: Econ from $391.- Oct-Dec
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 $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 > Liberia, Costa Rica: Biz from $946 Econ from $327. – Mar-May
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
BOS > Newark, New Jersey: Biz from $317 Econ from $111. – Feb-Apr (Including Spring Break)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
BOS > Krakow, Poland: Econ from $343. – Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Dubrovnik, Croatia: Econ from $374. – Jul-Sep
* This is a “fare dump” with a few alternate dates available.
BOS > St. Louis, Missouri: Econ from $158. – Feb-Apr (Including Spring Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
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 > Luqa, Malta: Econ from $372. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Fort Myers, Florida: Biz from $288 Econ from $99. – Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Pristina, Kosovo: Econ from $353. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Prague, Czech Republic: Econ from $348. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Indianapolis, Indiana: Econ from $154. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Dallas, Texas: Biz from $315 Econ from $117. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > San Jose, Costa Rica: Biz from $538 Econ from $235. – 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.…