surprise travel vacations

For years I would plan my trips down to a T. I would read travel books from cover to cover. I would spend hours online reading reviews of restaurants, attractions, public transportation routes, museum hours, and more. The last thing I wanted was to travel to a new place and miss out on something because of poor planning. To say I was organized was an understatement. There was little room for surprise.

Those that would travel with me would both love and hate it. They loved that they didn’t have to lift a finger during the planning process and they trusted me to find the best of the best things to do in every city. And boy was I good at that! On the other hand, they also hated it because our days were jam-packed with activities and sights to be seen, leaving very little downtime. Sleeping in? What’s that?! Although our days were sometimes non-stop, we always had a great time.

surprise travel experience

After years of being the planner out of my friends, something just switched in me, and I decided I didn’t want that responsibility anymore. I wanted to relax for a change. On recent trips, I did some preliminary planning mostly on how to get from Point A to Point B, but day to day itineraries went out the window. It is a lot of work to plan a whole two-week vacation! Some of my best adventures came out of plans going awry, or not having any expectations! In the last year, I’ve been on at least 4 or so spontaneous trips where we hopped in the car or on a plane and had no set plans other than to have a good time!

My lesson from all of this is that there has to be a balance between spontaneity and obsessive planning. Someone has to spend some time researching travel and transportation otherwise you may be sleeping in the world’s most expensive hotel or on the floor of a train station or airport.

But don't fret.

I found a solution.

Airport travel Surprise Trip

One of the new travel trends over the last few years is "surprise travel." Companies now specialize in planning trips for you, so you don’t have to. travel agencies have existed forever, but this is different, I swear! Instead of keeping you in the loop on every step of the planning process, they intentionally keep you in the dark. You don't book your flight or hotel, just fill out a quick survey and let them do the work for you. You may not find out where you are going until you’re at the airport and ready to check into your flight! How cool is that?

Here are a few surprise travel companies paving the way:

Magical Mystery Tours

Mystery Surprise Travel Tour San Francisco

We first start this journey with Magical Mystery Tours. To start, you tell them your budget, the dates you would like to travel and few other details to get them started in planning your next great adventure. You’ll have the opportunity to let them know what kind of travel you hate or love too. Maybe you hate the beach (in that case...who are you?!) and would rather check out bustling big city life. They can tailor your trip to you!

Here are just a few of the many things they take into account:

  • Openness to red-eye flights
  • Seat preferences
  • Whether your passport is 6 months beyond the travel dates
  • Openness to non-refundable travel
  • Will you want travel insurance for flights and/or lodging?
  • What airport you’d like to fly from
  • Where have you previously traveled?
  • What places have you loved?
  • What places did you not love so much?
  • Do you want to travel internationally?
  • Do you want an all-inclusive resort?
  • Hotel bed-size preference
  • Do you want to go to multiple destinations?
  • Is seasickness a concern?
  • Comfort with foreign/international destinations
  • Level of spontaneity
  • Interest in a rental car
  • Hotel preferences
  • Hot or cold? Urban or rural? Desert or tropical?

Once you’ve set those parameters the team will get to work planning your next trip. One week before your trip you will get the weather report for your destination so you know what to pack. A few days before your trip you will receive an envelope with the details of your excursion which is to remain sealed until you arrive at the airport.

Pricing begins at $1,500 for a 2 person trip for the weekend ($1,100 for a solo weekend trip). If you add additional nights or extra travel buddies, the price will increase. If you’re looking for a longer one week trip or international destinations, you should budget about $5,000 or more.

Magical Mystery Tours covers the important parts of your trip like transportation to and from your destination and your lodging. It does not include additional service unless you also hire them to book excursions or restaurant reservations, for example. You’ll want to give them about 6-8 weeks to plan your vacation.

Pack Up & Go

Train Surprise Travel

Next up on our list is Pack Up & Go. This company specializes in booking your surprise travel by air, bus or train for 3 days within the United States. They will book your transportation, accommodations, and create a curated list of recommendations for the city that you visit. Travel solo or with as many as three friends (if you have a larger group, you can contact them with your special request). Per person prices range from $650 to $5,000 depending on the trip you want them to design for you!

Like Magical Mystery Tours, Pack Up & Go also provides you with the weather report a week before your trip, as well as recommended items to pack (like your hiking boots), luggage size restrictions as well as your instructions on where to go to start your trip (train/bus station or airport, for example). A few days before you leave you’ll receive an envelope with all you need for your trip including directions to your accommodations and a city guide with restaurant/nightlife recommendations. Wait until you get to your departure location to open the envelope so you can enjoy the surprise!

Pack Up & Go’s travel survey includes some of the following questions/points:

  • Departure Date (2 night/3 day adventure)
  • Time restrictions?
  • What were the last 3-5 trips you took for leisure purposes (within the US)?
  • Do you have any upcoming trips planned?
  • Do you prefer action, relaxation, or culture?
  • What are some of your hobbies/interests?
  • Do you have any dietary restrictions?
  • What type of accommodations do you prefer?
  • Are you celebrating a special occasion?

The company doesn’t book any transportation that would take longer than 3-4 hours of travel time from your city of origin, so you know you’ll be spending more quality time in an awesome city and less time sitting on a plane, train, or bus.

Other Travel Agencies

Surprise Travel Trip Mystery View

While some companies are founded on surprise travel like the two above, there are plenty of luxury travel agencies which will also arrange a truly unique experience for you and add the element of surprise for you at your request. One of these agencies is Brown & Hudson. They use their expertise and connections to create a trip that goes above and beyond anything you could plan yourself. Some examples they’ve cited include introducing you to your favorite writer or politician or arrange a private tour of a museum with the curator of the exhibit or the architect.

If you live outside of the United States, companies like Surprise Trips can help you plan a unique weekend vacation. Surprise Trips currently offer 77 different destinations departing from the UK and Ireland, and you can exclude up to three destinations that you want to avoid. As with other surprise travel companies, they reveal your travel destination upon reaching your airport of departure. If you’re really in a pinch, Surprise Trips can plan a spontaneous adventure for you with 24 hours notice.

Surprise Flights

Travel agencies aren’t the only ones having all the fun. Airlines are also getting into the surprise travel business.

Luxury Travel Best First Class Cabins Plane

Dutch airline KLM has a unique approach to this with it's Monday Mystery tickets. The airline chooses between 4-7 top destinations in Europe each week. Each Monday they will list 100-200 mystery tickets for €99 (and a €10 booking fee per booking). Come Tuesday you will find which destination you’re headed to. Wednesday you’ll receive your ticket. You’ll depart on your trip on Thursday or Friday and return home on Sunday or Monday.

German airline Lufthansa launched Lufthansa Surprise this year which will help you book a flight to an unknown destination. Choose from one of nine different categories of trips including: bromance, partying, cities, sightseeing & culture, gourmet cuisine, nature, romance, shopping, and sun & sand. Each category has a list of 8 different destinations that fit that theme. Once you select a category you can de-select any of those destinations that you don’t want to travel to. Flights leave from both Frankfurt and Munich and you can book anywhere from one to 42 days in advance. Prices start at either €89 or €99 depending on the category and destination.

Your Turn…

travel mystery destination

Have you booked a surprise trip? What was your experience like?

What would you do differently?

Share your experience in the comments below!