Last Minute, Short Vacation Ideas for Memorial Day Weekend

May 22, 2019

By Rebecca Heilweil

This upcoming Memorial Day weekend, nearly 43 million Americans are expected to take to the "nation's roads, rails, and runways," according to AAA Travel. Meanwhile, the U.S. airline trade group Airlines for America estimates that nearly 260 million people will fly on U.S. carriers this summer.

These record numbers come amid increasing interest in shorter vacations that travelers can purchase closer to the last minute.

"Instead of taking those giant vacations once a year, at Conde Nast Traveler we've been saying take lots of little vacations," Conde Nast Traveler contributing editor Mark Ellwood told Cheddar. "Especially among millennials, we're seeing much more of a sense of 'rather than save up my vacation for one big trip, I'd rather take six or seven and split them up.'"

Some locations — like Mexico, Florida, and Denver — offer vacations that are closer to home (if you're based in North America) and easier to manage over a long weekend. "From New York, I'd send you to Mexico," said Ellwood, pointing to the city of San Miguel de Allende. He says it's "one of the places in Mexico which has superb air service to almost everywhere in America."

"It's this charming colonial city with incredible architecture," he adds. Alternatively, Key West in Florida, Ellwood says, provides "a slew of great, new resorts." For those who don't long for summers by the beach, Ellwood recommends Denver, which offers opportunities to hike and explore nature, as well as "a brand new, very-energized food scene."

When booking tickets relatively close to your trip, Ellwood recommends looking for hotel-flight package deals. "I think everyone is always terrified that at the last minute, you will get gouged," he says. "Because of the way that airline tickets are allocated, if you are flying at the last minute, it's often cheapest to buy a package." A package could effectively include the hotel for free, he says.

He also recommends negotiating. "I think when people think of negotiation, they think of waving their finger in someone's face and saying, 'give me a better price or I walk away,'" Ellwood says. "It's not like that at all."

Instead, he suggests calling the hotel around lunchtime and asking about rates. "They might have a few more rooms empty than they'd like," he says. "And if you're the polite person who says, 'hey, I'd love to come, but could you work a bit with me on the price,' why wouldn't they?"