We just returned from a weekend getaway to Barbados, and I wanted to share impressions on what I’ll term our first experiment in “extreme weekend travel”.
To fit nearly a week of travel time into one weekend, all you need are the following:
- two vacation days that connect to the weekend or a three-day weekend that you can stretch to four;
- a direct, red-eye (overnight) flight in both directions;
- a discount flight (under $300), ideally, to make the short duration worthwhile;
- an inexpensive destination or somewhere to stay.
We’re both trying to save our vacation days for a larger trip later in the summer, so this was an experiment born of necessity — taking only two vacation days, we managed a full four-day vacation. As noted, this required a red-eye flight in both directions and a return straight to work from the airport.
A direct flight was essential, since changing planes in the middle of the night will ruin your chances at arriving rested to your destination.
Thanks to The Flight Deal and a great deal on JetBlue, we were able to get an overnight flight direct from New York (JFK) to Barbados (BGI) for $192 round-trip. We departed at 9pm on Thursday, arriving at 3am and returned at 4am on Tuesday, returning at 8:30am to New York.
We survived, and on the return flight we both slept soundly, thanks to the extra leg room and comfy seats on JetBlue. There was actually enough room in coach to fully extend your legs under the seat in front of you and stretch out. Bring your own pillow and blanket, however, as they carry an extra charge.

Destinations
Flying from New York to the Caribbean allows you to get far enough away for a real vacation, visit a foreign country, yet stay in a similar time zone.
JetBlue flies to dozens of destinations in the Caribbean and from my experience, many of these flights are direct and of the overnight variety. Their flight map can be consulted here.
Norwegian flies from JFK to Guadeloupe and Martinique and offers some great deals, though these are daytime departures and would require an extra day of vacation.
If you’re looking to fly domestically, nonstop cross-country flights, i.e. JFK to SFO, OAK, LAX, LGB offer the chance to get some rest, though jet lag can be an issue if you’re returning straight to work. Given the time zone difference, the return (West-East) flight needs to be overnight, though the East-West flight only takes 3 hours and could be done in an evening.
Searching for Flights
Use ITA Matrix to search for arrivals and limit the selection to flights departing at night or early morning.
For flights in a similar time zone, also select “Early Morning” and be sure that you’re searching for nonstops. Running a search to a series of nearby destinations, as shown below, can be very useful if you’re just looking to get out of town.
I hope these tips inform and inspire. Good luck in planning your next Extreme Weekend Getaway.
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