VIP Traveler Is the Best New Travel Planning Tool You Didn’t Know You Needed

Travel takes you to the highest of highs. The planning? The lowest of lows.

To start, there’s the matter of figuring out exactly where to go, booking airfare, seeking accommodations and then, of course, not least of all, how to finance said airfare and accommodations. Now tie in all of the added obstacles that come with traveling in a post-pandemic world: airfare at a premium and an abundance of cancellations and delays, among them. It’s stressful enough to make you wonder if all that rest and relaxation on the other end is even worth it.

Enter VIP Traveler. VIP Traveler is a new, and free, subscription service that uses “proprietary personalization technology to ensure the right trips reach the right people” — not dissimilar to Stitch Fix. (For the uninitiated, Stitch Fix is a personal style service that, due largely to the enrollment survey, offers users a totally customized experience. VIP Traveler functions, more or less, the same way.)

To put it to the test, I signed up for the free version of VIP Traveler. The survey comprises 20 questions that are obviously meant to establish a traveler profile. Examples include: “When traveling for pleasure, how do you typically fly?” “How much do you look to spend per night at a resort?” “What kinds of hotels do you tend to stay at?” “How does your work schedule impact your travel?” “When you travel for fun, who do you travel with?” and a series of “would you rathers.” It then concludes by asking what destinations you’ve been wanting to visit.

I kept my answers honest: as travelers go, I’m pretty middle-of-the-road. When traveling for pleasure, I almost always fly economy. I don’t stay in hostels, but I don’t stay at 5-star resorts, either. I use my points to travel, but I’m not exactly “The Points Guy.” I travel with my partner, my family and my friends, depending on the occasion, but sometimes I travel alone, too. The destinations I’ve been wanting to visit include cities in Australia, Italy, Africa and Greece.

I say all of this because, at least in my experience, there are an abundance of travel planning tools for thrifty travelers, and just as many for luxury travelers, but there aren’t nearly as many for just…regular travelers. Of course, VIP Traveler isn’t necessarily for any one of those categories in particular, I just mean to say that I wasn’t exactly holding my breath for my results.

That said, my first set of recommendations included two of my all-time favorite cities and two others that I’ve long been wanting to visit, none of which I’d mentioned in the survey, with a full rundown of places to stay and deals attached, which placed said accommodations firmly within my budget. The following week — to my pleasant surprise — I received my new “Travel Finds” with all new destinations that all felt, once again, very in tune to my taste. I couldn’t believe how well it seemed to know me despite still having never booked anything, and subsequently allowing them to mine more data. According to VIP Traveler co-founder Josh Borenstein, that’s exactly the point.

“It’s a place where you come when you want that trusted ‘friend in travel’ — someone to help guide you when you need inspiration, advise you when you want the low-down on a particular destination or hotel and to help you get the most out of your trip when you do decide where to go,” Borenstein says. “By that, we mean not only the best rates, but you also get benefits of not being an anonymous booker on Kayak or booking cold. When you book with us, you get looked after.”

For his part, Borenstein’s no stranger to the travel space. Aside from being an avid traveler himself, he also co-founded a business that specialized in flash sales, with a strong focus on travel. That said, his end goal was always to build a business that “made it easy for people to take more trips and discover parts of the world that might not have been on their radar, but do it in a really different way to the ‘same old.’” That method, he claims, is mostly broken anyway.

“There’s just too much content and too much time wasted on looking at options — and it’s hard to actually decipher the nuanced truth from review sites. We thought there was a way to bring personalization to the travel booking experience through a combination of proprietary tech and the human touch of our connected ‘Travel Stylists,’” Borenstein says.

Plus, he adds, “The on-the-ground situation changes weekly, both in terms of regulations and how hotels are handling the post-pandemic rush. Some hotels have gone down the gurgler in terms of maintenance and can’t attract good staff while others are crushing it. It’s handy to know which is which. Additionally, the flexibility of our ‘buy now, travel later’ options with free date changes and cancellations gives additional optionality.”

That optionality only increases with the VIP Traveler+ option, too, which gives members access to on-the-ground destination experts for local advice, a personal “Travel Stylist” for custom trip planning, 24/7 support and VIP benefits with all bookings. While certainly not the best option for the scant traveler, for those who are jet-setting even a handful of times a year — it’s worth the (what some might consider) lofty price of admission (it’s currently $495 a year). In fact, according to Borenstein, your first trip with a VIP Traveler+ membership is likely to pay for itself.

“Not just in terms of accessing the best rates, but the experiences offered, the access to opportunities you’d never know about and the ease by which you can contact us regarding those little details that you’d never be able to ascertain yourself or via a traditional online travel agent,” he says. “Even members who belong to platinum credit card travel services aren’t able to offer on-the-ground advice or negotiate on your behalf for bespoke treatment.”

And if you’re not in the market to book a trip? It’s also a great one-stop-shop for travel inspo. In addition to your weekly “Travel Finds,” there’s a bucket-list building feature, which allows you to specify the destinations you’re interested in going to. It’s what inspired Borenstein’s upcoming trip to the new Buahan by Banyan Tree in Ubud, Bali. (“There is literally nothing like it in the world and we’ve got access to an incredible opening offer.”) And, most feasibly why, I can’t stop dreaming about a trip of my own, to Corfu.