Spontaneous Travel

Preparing for Spontaneous Travel

By EMILY BRENNAN

 

WHEN Sam Shank began HotelTonight, a last-minute hotel booking app, two years ago, he thought its typical user would be a business traveler in need of a place to lay her head.

HotelTonight

Sam Shank, founder of the HotelTonight app.

Turns out the app also appeals to impulse travelers, with some booking rooms at 2 a.m. for that night (or rather morning).

“They said, ‘Hey, instead of going home tonight, let’s do a hotel stay,’ ” Mr. Shank said. “That’s something we’ve set as a company goal: to make the world a more spontaneous place.” For revelers scrambling to make plans for New Year’s Eve, below are edited excerpts from a conversation with Mr. Shank on booking (very) last-minute travel. 

Q. A paradoxical question: how do you prepare in order to be ready for a spontaneous staycation?

A. I keep an overnight bag at my desk with a change of clothes, toiletries and a phone charger, just in case. On my iPhone there are a couple of must-have apps. Of course, HotelTonight. Sales go live every day at noon, and you can find discounts on high-end hotels or something more no-frills. There’s also GrubHub, which allows me to order food anytime to any hotel, if I want something different from room service. WillCall, an app for last-minute concert tickets, which is only in San Francisco, but it’s coming to Los Angeles and New York, too. And Score Big, a Web site that lets you get tickets to sporting events that night.

Q. What if you’re looking to explore a new city?

A. Good discounts on last-minute flights are hard to find because airlines make more money off targeting corporate customers and raising prices, but it’s possible. Pay attention to the e-fares from carriers like United or Delta that appear on Tuesdays. They’re reduced fares just for that upcoming weekend, and the destinations change every week, so it’s good if you have flexibility with where you want to go. Or do a road trip. There are so many great places within a couple hours of major cities. Napa Valley is a bit rainy this time of year, but the whole lifestyle — luxurious accommodations, incredible culinary scene, winemakers — that doesn’t change, and comes at a third of the price. Same for Newport, R.I., popular among our Boston users.

Q. Any tips for car rentals?

A. Getaround is a car-sharing site and app based in San Francisco, but it’s expanded now to Austin, Portland, San Diego. It’s like an Airbnb for automobiles. You not only save money, but you also could rent someone’s car that’s a lot more interesting than your run-of-the-mill airport rental.

Q. You’re in the new city. Now what do you do?

A. Foursquare is great for finding out what’s popular in a new city, or even your own city. Their recommendations are more trustworthy than other sites operating only on ratings and reviews. Foursquare’s looking at the number of people checking in to a place, and how often, the types of people, and how similar they are to you. You’re getting visitation data, not just review data.

They have a great international presence, too. When I was in London this summer, I looked on Foursquare for a bar near my hotel. Walked to this crazy little bar, tucked away in this tiny street in Chelsea. England was playing in the Euro soccer cup, this really tense game. It was this quintessential London experience, capped off by the fact that Prince Harry was in attendance.