Mystery Trips – The Mystery of Mystery Trips

What is a mystery trip and how do you plan it?  I get asked that question a lot.  We travel a lot. Sometimes we look for quick getaways rather than longer trips. Occasionally we want them to be super low-key.

I am a planner by nature, which is probably why I usually plan all the trips for our close circle of family and friends. Sometimes, though, I want someone else to take the reins. Hence the advent of the Mystery Trip.  Our first Mystery trip was born out of the frustration of not knowing where to go for yet another long weekend.  I was tired of planning, but I still felt like I needed to utilize the upcoming long weekend to its fullest potential.  I am not one to miss out on a vacation day and neither should you.

I needed to come up with a new and better trip planning method.  How could I plan a trip but not spend tons of hours planning?  And how could I wow my husband with my spontaneity?  My planning nature didn’t usually leave much to chance on a trip.  I usually have a trip fully planned, right down to fully printed itineraries.  This trip was going to be different.

How Do You Plan A Mystery Trip?

What exactly is a mystery trip and how does it get planned? A destination gets chosen and a hotel gets booked and the rest of the trip is planned by the fates.  I will say that I do advocate using a travel agent to get your hotel booked.  Once you lock in on a destination they know the area and can recommend a great hotel.

Let me give you an example of how our first mystery trip went down and I will start out by saying that these trips do require a bit of planning.  Luckily for me, they don’t require the usual full-blown itinerary, with color coded, day-by-day trip plans and every detail mapped out.

These trips allow you to flow more and enjoy your time as it is happening or move on to something new if the day just isn’t vibing.

Get Started

Plan these trips over a long weekend as they require three nights to get a real sense of any destination.  We had a long weekend coming up over President’s weekend. I did a ton of research to figure out cool places we could visit that were in easy driving distance.  Why not try and surprise my husband for our weekend away and save myself a ton of the hassle of planning at the same time.  I liked the idea that he wouldn’t know where we were going until we arrived.  Or at least almost…

So I started by selecting a place that neither of us had been to and I booked a hotel that came recommended on TripAdvisor.  I am a travel agent and have been one for over 16 years, so I didn’t call another travel agent, that just would have been weird, although I do call them for long complicated trips that are not my specialty.

Suggestion:  Look for hotels that include breakfast if that is important to you, or one that offers spa treatments if that is what you are after on a long weekend trip.

For this inaugural mystery trip I selected 18 local attractions in the area and wrote them on slips of paper. The slips were folded, stapled and sealed in an envelope that was marked “Mystery Weekend”.  Kind of cheesy, I know, but at least I didn’t throw the envelope away by mistake. Restaurants in the area were researched on a variety of websites and were included on slips of paper in a separate envelope.   What would have taken me many hours to plan, ended up taking me 2-3 hours.

Taking Off

When the weekend arrived, I got to the car first and set the navigation system for the hotel. I  wanted it to be a secret for as long as possible, but knew he would figure it out quickly as he was doing the driving. With our weekend bags packed we hit the road for the mystery.  We stayed at the Hyatt Place Dewey Beach.  Check-in was a breeze as I had done pre-check-in before we arrived, so we were just handed our keys to our room.  Parking was free at the hotel and so was the breakfast.

The Trip Continues

We woke up Saturday morning and after a hearty breakfast the mystery trip officially began.  My husband selected a slip from from the envelope and we were off to our first destination. We hit a lot of local sites in the area, like Rehoboth Beach, Ocean City, MD and the wild horses of Assateague Island. We went beach-combing, hiking and to see a lighthouse.

Nothing was planned, we just did one thing and when we were done with that picked another random thing to move on to.  We had some awesome meals and relaxed not knowing what adventure was up next.

What’s Up Next…

It was a great relief to just let the trip plan itself. As a planner, it is nice to give up control. We have done other mystery weekends since this first one.  We visited both Cleveland, OH and Newport, RI. Both long  weekends and both with tons to see.

So my parting advice would have to be to make life a mystery! Don’t plan everything. You will find unexpected places and learns new things about yourself and the world around you.  You will even have some fun along the way. Give up control. As hard as it was for me, it led to an amazing trip.  It can be liberating.

Super Travel Bitch Out!

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  • Alexx
    Posted January 8, 2019 2:16 pm 1Likes

    A mystery trip sounds both exciting and like it can cause a lot of anxiety! It would take a lot for me to let go of my plans but once I did it, I think that I would really enjoy a mystery trip!

    • Super Travel Bitch
      Posted January 8, 2019 7:10 pm 0Likes


      It did cause me a bit of anxiety the first time but less and less each subsequent time we do it and we find such cool places along the way.

  • Angelica
    Posted January 8, 2019 3:22 pm 1Likes

    I love thess kinds of trips and I’m glad you had fun despite being a planner! You just get so much better information from people who live there which is why I don’t plan much until the trip:)

    • Super Travel Bitch
      Posted January 8, 2019 7:09 pm 0Likes


      I wish i could be more like you. I stress over the planning. This kind of a trip is my way to go away without stress. And surprise my husband and not much surprises him after 30 years. 😜

  • Greg
    Posted January 9, 2019 1:53 am 0Likes

    This is a great idea. Do you plan these for other people? I would love for a trip like this to be a complete mystery for me and my partner. It would be better to have the whole thing a surprise.

    • Super Travel Bitch
      Posted January 9, 2019 3:05 am 0Likes


      Thanks for the feedback. I don’t plan them for other people now, but you have me thinking. Keep checking back on the site, I may just add a new feature. I like the idea. I could see how people would like it to be a total surprise.

  • Sage Scott
    Posted January 9, 2019 3:26 am 0Likes

    While I love the concept of a mystery trip, I’m not sure this firstborn (read: control freak) could really let go and do it. 🙂

    • Super Travel Bitch
      Posted January 9, 2019 3:33 am 0Likes


      I was skeptical at first too, but am sooooo glad I tried it. It really allowed me to experience things I would not have otherwise. We just let the trip roll. I understand the control piece, though. I am so type A. Makes it hard to give up that planner in me too!

  • Cynthia Mackintosh
    Posted January 10, 2019 7:36 pm 0Likes

    My husband has surprised me with a couple of weekend “mystery trips” and they were so much fun! I’m a planner by nature, too so I can understand where you’re coming from.

    • Super Travel Bitch
      Posted January 15, 2019 1:19 am 0Likes


      It is so much fun when others do the planning. Even when you are a planner, it is good to give up the reigns at times.

  • Becki
    Posted January 10, 2019 9:10 pm 0Likes

    I’ve seen these ‘mystery trips’ advertised before as well as having friends who have done them but I’ve always steered clear of them worried that I’d be dissapointed and wasting my precious holiday time. Maybe time to bite the bullet and don’t know it until I tried it, I hear so many good things, I just need to have the guts to let someone else do the planning for me.

    • Super Travel Bitch
      Posted January 15, 2019 1:21 am 0Likes


      Get the guts. It is so much fun. I was afraid the first time, but sooooo glad I did it and so was my husband. He loved, not knowing what was coming up next and me not having the menu memorized before we got to the restaurant. 😉

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