The Rise of the Surprise Vacation

The plan for everyone who hates making plans.

Vacations are amazing. Vacation planning? Not so much. Even when you go in with the greatest of intentions and excitement, you're soon left looking at 293 websites, trying to figure out schedules, best prices/packages, and just how much you can pack in your carry-on luggage—which generally leaves you with one question: Is there alcohol around? 

But now there's a whole new movement on the rise: surprise vacation packages. If you're the kind of person (ahem) for whom the anxiety of preparing for the vacation ruins the actual vacation, more and more hotels are offering packages to help you out. Here, a look at some of the best ways to get in on the trend and plan that vaca for next year right now.

Last-Minute Scheduling's new app "Booking Now" lets you dip your toe ever so gently into the pool of surprise vacations by having you book any one of their open hotels the second you arrive to your destination (or, okay, a few days before). Literally open the app and play a game of Travel Tinder—swipe left if you're not interested and right if you are, then book on the spot. The best part is that you can save a ton of money—and get a swanky place to boot. There's also HotelTonight, which offers less variety of hotels, but is one of the oldest (and trusted) last-minute booking apps for your stay. Don't know what city (or country) to hit up next? Try Google Flights, which allows you to plug in things like "beach" or "Europe" from your home (or starting) airport, then filter by airline, price, stops, etc. for the best deal. (Obviously the best way to plan a weekend getaway.) Kayak also features a program called "Explore" which lets you take a glimpse at prices to a number of places, while also filtering for price, weather, flight time, and more. 

Change in Execution

If you're already using online booking sites to plan your vacation, you basically only need to change tabs or open a new window. Expedia, Hotwire, and CheapCaribbean all have their own versions of surprise vacation planning programs. All feature the ability to click the region you want, and book a flight and hotel—without you knowing exactly what hotel roof you'll be sleeping under until days to hours before your flight.

Complete Adventure

Want a totally unplanned, don't-know-where-you're-going-until-the-last-possible-minute getaway? Here's your chance. Magical Mystery Tours has been planning "unknown" trips for years. Payment includes transportation and accommodations, and a week before the trip you'll receive a weather forecast, packing list, and a check-in time and location. Some days later, you'll receive a folder with all the details of your trip, which you can either open then OR for the full experience—open when you get to the airport.

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Samantha Leal
Senior Editor

Samantha Leal is the Deputy Editor at Well+Good, where she spends most of her day thinking of new ideas across platforms, bringing on new writers, overseeing the day-to-day of the website, and working with the awesome team to produce the best stories and packages. Before W+G, she was the Senior Web Editor for Marie Claire and the Deputy Editor for, with bylines all over the internet. Graduating from the Medill School of Journalism at Northwestern University with a minor in African history, she’s written everything from travel guides to political op-eds to wine explainers (currently enrolled in the WSET program) to celebrity profiles. Find her online pretty much everywhere @samanthajoleal.