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The layover gets a do-over

Miami. Sean Pavone/Shutterstock/Sean Pavone

For most travelers, “layover” is a dirty word. It usually means roaming the colorless halls of an airport to kill time or stockpiling tabloids for a long date with the hard-backed chair at Gate A20.

Layover limbo can be particularly frustrating when you’re stuck in the airport of a city you’d otherwise like to explore. Given the layover’s bad rap, booking nonstop flights or flights with the shortest layover possible are obvious ways to avoid mid-trip misery. But what if a long layover could actually enhance your travel experience?

It turns out that it’s relatively easy to book a layover (think: eight hours to overnight) that gives you enough time to sightsee in the city. Plus, you can typically secure this “adventure layover” without compromising an affordable rouand-trip fare.

One way to incorporate an adventure layover is by using online booking tools to find your flights. For example, Boston-based travel search engine Kayak allows travelers to find the most affordable airfares to a desired destination by identifying the cheapest routes across all carriers. According to Kayak’s chief technology officer Giorgos Zacharia, you can modify your flight search to intentionally filter for routes with long layovers.

“By default, we hide such trips from the user because most people don’t book them,” says Zacharia, “But you can easily uncover these options on Kayak.”


Zacharia recommends unselecting Kayak’s “Hide X longer flights” option under the left-hand Flight Quality section. Assuming you only want one long layover, limit your search to one stop. Then, set a price maximum so that any flight with an adventure layover doesn’t exceed the reasonable airfare you’ve found on another flight.

Once these filters are selected, you can sort the flight options by duration from longest to shortest, so that flights with the longest layovers appear first. You’re also not locked into a long layover in both directions — you can select the adventure layover itinerary that you like, and then modify the sort to choose from the shortest return flights.

Zacharia adds that more advanced users can even use Kayak’s multi-city search to add additional days to your layover — but this could end up costing more. A long layover will always appear automatically on your search if it saves you more money than a shorter flight, thus eliminating the need to modify any filters.


Other travel search engines like Momondo, Google Flights, and TripAdvisor allow you to play around with adding an adventure layover to your flight, although Kayak offers more extensive sort and filter functions.

If you’re someone who jumps on cheap airfares as an excuse to get away, an adventure layover might be an added bonus. George Hobica, founder of low airfare alert site Airfarewatchdog.com, says that some of the best deals require that you have a lengthy layover — often extending overnight.

“We see [these itineraries] all the time on fares from Boston and other US cities to Europe on Turkish Air via Istanbul,” says Hobica. “We also see this to the Caribbean on American Airlines with overnights in Miami.”

Hobica says you can sometimes save $500 or more on airfare by overnighting, instead of choosing a quick connection or a nonstop flight. However, these deals generally apply only to specific itineraries. “Usually an airline will only allow you to choose a layover [at your request] up to four hours before charging extra,” Hobica adds. “But if the airline is giving a price break for the ‘inconvenience’ of a long layover, then you save tons of money.”

Booking an adventure layover is possible even if you prefer to go through a travel agent. Christine Stewart has operated Stewart International Travel in Brookline since 1984 and often customizes itineraries for clients who want to extend their stay in a layover city. Stewart says that foreign carriers in particular, such as Iceland Air and Copa, are known to encourage free layovers. Choosing a destination with a lot of air carrier competition can also increase your chances of securing an adventure layover on the way.


Another option is scheduling a late departure so that it misconnects with the final leg of your flight, forcing an involuntary layover, says Stewart. However, some airlines may require you to take the next available flight when you “miss” your connecting flight. Stewart adds that to keep your airfare affordable, your layover flight must still be considered a connection; if it’s truly a stopover, the fare will increase.

Stewart says that adventure layovers are sometimes difficult to predict because flight rules and regulations are always changing. Ultimately, your options for incorporating an adventure layover into your flight are limited by where airlines stop and connecting flight schedules. But if you’re willing to investigate different route options and be flexible about where you stop along the way, you can break up your flight with an extra excursion.

“I love to travel — that’s why I got into this business,” says Stewart. “The idea of going somewhere and not being able to see anything is kind of heartbreaking.”

Samantha DuBois can be reached at duboissd12@gmail.com.