Sam Shank has been a travel junkie for almost his entire career, logging periods at search engine DealBase and pioneering hotel review site TravelPost, which Kayak has since absorbed. Now he logs up to 100,000 miles a year as chief executive officer of HotelTonight, a slick last-minute booking app he co-founded in 2010. When he’s not at home in San Mateo, California, with his wife and two young sons, here’s how he makes the most of his time on the road.
– How to keep the light at bay in any hotel room
I’m a fairly light sleeper and need a quiet, dark room. One of the pet peeves I have in travel is having the sun come in on either side of the curtains in the morning, especially when I’m trying to avoid jet lag. So I’ve slipped a couple of binder clips into my briefcase to get those curtains to connect, or hold them together. Recently, though, a friend told me I was wasting my time packing those extra things. Instead, he told me to use the coat hangers from the closet-the ones with clips that hold your pants. They work just as well as a binder clip, though it does look kind of funny.
– Beating dehydration takes more than bottled water
When I’m traveling, I always get dehydrated, but water is not the best thing to drink because you’re not getting all the electrolytes, potassium, and salt. So I always take these tablets called Nuun with me. They turn water into a sports drink-only healthier, because it doesn’t have much sugar. They don’t take up much space, and you can get them safely through security.
– The virtues of never planning a trip-and which app is best for remaining impromptu
I don’t do a lot of planning, setting up dinners or reservations, because I don’t know what I’m going to feel like doing. It’s how I’m wired. As a tool when I arrive, TripAdvisor has great reviews. But all of them are written by travelers, so even the highly recommended places are inherently tourist traps.
To look for recommendations from locals, I use Foursquare. It helped me with one of my favorite times in London a few years ago. I was originally scheduled to sleep off my jet lag, but when I got there I thought: Huh, I’m not tired, so I’m going to do something. I was in Belgravia and looked on Foursquare for bar recommendations, and I chose one down this little alleyway. I walked in, and there was a football match on. It was England vs. Sweden, and at the last second, England came back and won it. And sitting in the corner was Prince Harry. It was a really crazy, fun night, when I made a lot of friends.
– His favorite secret hideaway, just a short flight from the U.S.
My most recent trip was to the Dominican Republic, to the north shore. We did a few nights first on the south shore, and it was nice, but it felt like a little American enclave, and that’s not why I travel. On the north coast, though, we stayed at the Playa Grande Beach Club. It’s a fantastic design, with wonderful people, and you can get an hourlong massage for $20. The area is still very rugged. The beach is one of the best I’ve ever been to, and there’s an Aman on one end, and this resort is on the other.
– The best winter jacket for packing light
I was going to Chicago for an event, and it was forecast to be 20 degrees. I’ve lived in San Francisco for 20 years, and I’ve almost forgotten how to dress for the cold. I don’t even have many cold-weather clothes. Even worse, when you’re packing, big jackets can take up a lot of space. But the down-type, poofy jackets from Aether compress really small. I could fit two of them into my bag, and I wore them both. My friends definitely thought I was ridiculous, but it was very practical.
– One view he hasn’t tired of, in 20 years of visiting
My parents first took me to the Mauna Kea resort on the Big Island of Hawaii in 1996, and I’ve been going there on and off-for anniversaries, birthdays, significant events-every two or three years since. We don’t have a favorite room, because we don’t stay in the room that much, but the view from the Circle Bar down on the beach at sunset … you can sit there and look out forever.