Surprise_Vacay

A Guide to All the Travel Startups Offering ‘Surprise Vacations’

It’s like Russian roulette, but for travel: They do all the planning — and you don’t even know where you're going until it’s too late

I’ve been floundering about trying to book a vacation for months now. Oh, look, roundtrip flights from L.A. to Austin are under $100. But what about this Los Cabos all-inclusive package for $600? How about I just sit on my ass and book neither with no hope in sight?

Part of my inability to book a vacation stems from decision fatigue. There are so many choices. I’m also a horrible cheapskate, and love to flagellate myself by spending hours looking at travel options, fantasizing about them for days and deciding, after all that torture, that I don’t deserve to drop the money on it. And even if I did, that would mean endless hours scanning TripAdvisor reviews for hotels, countless travel sites for activity recommendations, lists of food I can’t afford, personal-finance sites to figure out how to pay for it with imaginary points… the list goes on. Let’s face it: Travel is a ton of work, and it often feels too intimidating and time-consuming to do right.

But let’s say someone could take the problem out of my hands. Let’s say someone else did all the decision-making for me, and now all I have to do is drop a flat fee; everything is taken care of. I truly wouldn’t care where I was going — I’d sign right up.

Look, it’s not the fucking 1970s anymore, I’m not going to go call a travel agent or waltz into my local AAA office. No, I’m going to find some startup’s sleek mobile-friendly website with neat typography and have them deal with it. Like a civilized, modern woman.

Beyond taking the where-to-stay and what-to-do problems out of booking a trip, some companies will even decide where in the world you should go. The catch, though, is that they won’t tell you where you’re going until a few days before your departure.

Enter the surprise vacation.

Here’s an overview of the different companies who will finally get your high-strung, over-planning self on a trip.

Nimbus: An Affordable Locked-In Rate

If your budget is small and you just like the idea of getting out of the house, Nimbus is for you. The prices are tiered, starting at $250 a person for a three-day trip leaving from a major airport. Each additional night costs $100 more per person, with the option to upgrade from a three- to four-star hotel and add a carry-on for an additional $100. When you leave is up to you, though there is a fee for high-demand holiday weekends. Other than that, the prices are set. The only other factors Nimbus considers in planning your trip are the three “interests” you select out of nine choices: local food, arts & sights, party, shopping, go exploring, relax, sport events, meet locals, or concerts & festivals. The costs incurred from these interests aren’t included in the package, but the company will use the info to select your destination.

Lastly, you can tell Nimbus where you don’t want to go from a selection of 15 cities. This is probably an indication of the possible places you could end up. From Los Angeles, for example, some of the options include Vancouver, Denver, San Antonio, Silicon Valley and Chicago. For the love of God, do not send me on a trip to Silicon Valley. You’d have to pay me $350 to go there.

Considering you can get a three-night trip for two with direct flights and city-center hotels for $700 total, it’s definitely not a bad deal. They also have a Euro-trip option for eight nights at $800 a person.

Pack Up & Go: Customize Your Surprise

So maybe you’re a selective little bitch who nevertheless appreciates the concept of a surprise vacation. Pack Up & Go allows for the most flexibility and preference in their planning, though these trips are exclusively three days and two nights. Rather than having a flat fee like Nimbus, Pack Up & Go works according to how much money you want to spend, between $400 and $5,000 a person. That price goes toward flight and hotel, with any remainder of your budget allocated toward food and activity recommendations.

When booking, you fill out a survey that asks for all your logistical needs and preferences. You tell them where your last five trips were and where you’re planning on going next, so they won’t send you there. The survey also asks you to select whether you’re most interested in action, relaxation or culture, and then has you check off your hobbies and interests, ranging from fine dining, flea markets, comedy clubs and LGBT-oriented spots. They also give the opportunity to list dietary needs and “anything else [they] NEED to know,” which is good for people with disabilities or specific desires.

A week before you’re set to go, the company will email you the weather forecast of where you’re going and any specific items you might need, so you can at least get a sense of how to pack. This email will also tell you what time to head to the airport.

A few days before your departure, they mail you an envelope with all the details of your trip. They tell you not to open it until you get to the airport, but I mean, it’s your life.

The Vacation Hunt offers a very similar service, with the added fun of clues and hints as to where you’re going in the weeks prior. They are a bit pricier, though, at $750 a person for three-to-four-day U.S. trips.

Get Lost With Black Tomato

This one’s for the rich psychos whose late-capitalist hearts are so devoid of joy that they need to be physically dropped in a remote corner of the earth in order to feel alive again. Get Lost wants you to really be lost. It basically lets you pretend you’re Bear Grylls, but glamping. Basically, they coordinate an expedition for you to embark on, and provide you with a kit and equipment containing a satellite phone and the right clothes for your environment. “Your journey will be closely tracked by Black Tomato’s experienced expedition operations teams as a safety net. You won’t see them but they’ll always be able to see you,” the site reads. Once you’ve completed your journey, they throw you a celebration, “something deeply personal and indulgent.”

Given that it’s a luxury service, every aspect of the trip is tailored toward your desires. While your only true decision is the time of climate/terrain you want to be in, you’ll be assigned a “travel expert” who coordinates your trip and determines “how lost you want to be.” According to a New York Times article on the service, travellers may end up in such places as Mongolia, Svalbard or Guyana: “Prices per person vary depending on destination and level of support. A recent three-day trek in Morocco was priced at $5,800 per person, and a seven-day private trip to a more remote location starts at $20,000 per person and includes 24-hour on-the-ground support and supplies.”

Personally, I’m just trying to get myself to go someplace other than my apartment; it’s hard enough dragging myself to the office every day. So if anyone wants to surprise me with an unplanned adventure, who am I to say no?