The surprising joy of surprise travel

I had the pleasure of going away for the weekend last Friday, without knowing where I was going. And it was amazing!

It all started about two months ago, when my wonderful daughter was home visiting for a few days, and we were talking about needing to plan a mother-daughter weekend. It’s been a while, but we’ve had some fantastic trips together — Las Vegas, Victoria, New York, to name but a few. Since she now lives on the East Coast, and I’m on the West, we thought we’d do some research and find a destination that we could both get to in about the same amount of time on a non-stop flight… and then she told me about a travel site she’d heard about, Pack Up & Go.

From the Pack Up & Go website

Here’s the deal: Pack Up & Go plans three-day weekend trips with surprise destinations (US only). You pick the dates you want to travel, pick whether it’s solo or multiple people travel, and whether you want a road trip or something involving planes, trains, or buses. For us, we clearly needed planes, since we’d be starting from opposite sides of the country. Next steps:

We put in our personal info and our starting airports. Then we answered some questions on a brief questionnaire, checking off the things that we like best on vacation (outdoor activities, history museums, lots of walking, used book stores, etc). We listed the most recent places we’ve traveled and any upcoming trips, so we’d be sure to end up someplace different. Next, we set the budget from their drop-down menu of choices (the price covers the airfare and hotel), paid by credit card, and… nervously… hit submit.

Our dates were confirmed on the spot — and then we waited. The whole idea is not to know in advance where we were going. On their FAQ page, my favorite question was along the lines of “what if I don’t want to go where you send me?” And basically, the response is — this is an adventure! If you can’t be open to whatever comes your way, this might not be the best travel option for you!

Well, my daughter and I were definitely into it — although I admit that I had some worries after the fact about being sent to some godforesaken hole in the wall with one motel and tumbleweeds blowing by. (No, that wouldn’t happen — the company wants to send its travelers to fun and exciting destinations, so they’ll tell all their friends, after all.)

One week in advance, we got our first pre-trip email, with the weather forecast (highs in the 70s, lows in the 40s), and a few packing tips: Bring good hiking/walking shoes, bring cameras for the nice vistas, and come hungry, because this is a city known for its food. Intriguing! I was guessing mountains, deserts, Southwest perhaps? My daughter shut me down when I started trying to share my thoughts, with a simple text: “Speculation leads to disappointment.” Ah, so wise.

Next, we each received a big envelope in the mail, sealed of course, with a reminder to wait until the day of departure to open. A day before, we got reminder emails about what time to be at the airport, an update on the weather, and the promise that Pack Up & Go would handle our flight check-ins, so our boarding passes would be ready and waiting for us in our email boxes on Friday morning.

I tried to cheat and convince my daughter to open the envelopes together over the phone on Thursday night, but she was not having it. Again, so wise.

So, Friday morning… I woke up at 5 am for my cab to the airport, poured myself my first coffee of the day, and opened the envelope… and here’s what I found:

And then…

Yay! I’ve never been to Denver, or anywhere in Colorado! So psyched! DD (darling daughter) was already at her airport on her side of the country, but we had time for a few excited text exchanges before we were off! The flights were perfectly synced — we arrived in Denver within 10 minutes of each other. Added bonus: It was May the 4th, and the Denver airport arrivals area was filled with Star Wars characters and paraphernalia, and we got to meet some very cute little droids.

The trip worked perfectly. The envelope from Pack Up & Go included directions for getting from the airport to our hotel (easy, comfy $9 train ride), lists of restaurants to try, ideas for activities, an Uber gift code, two tickets to a food tour, and two tickets to the botanical gardens. Score!

It all worked like magic. Our hotel was lovely and comfortable, right next to Union Station, which was a surprisingly lovely train station and hang-out spot. We were in walking distance of a great park (where we sat on a hillside to read every day), cute neighborhoods, plenty of coffee shops and restaurants, and just about anything we’d need. To go further afield, we took advantage of the Uber credit, even to go to Red Rocks for a morning hike.

Denver itself is a beautiful city, with gorgeous views of the mountains, plenty of great eating, and so much to do and see. The food tour was terrific — although certain items (pig’s head!) were just not for me. That’s okay, I more than made up for that with the home-made churros we had for dessert. Lots of walking, lots of exploring, and lots of mother-daughter time. What more could we have wanted? And the cool thing is that I probably never would have come up with Denver as a destination on my own. Now that I’ve been, I’d love to go back and see even more!

On the day of departure, we enjoyed the botanical gardens and a nice lunch before heading to the airport for our evening flights home. Once again, perfectly coordinated, so that we took off within about 10 minutes of one another.

Would I travel with Pack Up & Go again? Absolutely! There’s a great sort of joy in having the anticipation of a trip and knowing that the destination will be a surprise. We were 100% confident that we’d have fun wherever we went, and from looking at the website and seeing all the great photos of other travelers, we knew we’d end up somewhere amazing. I’m usually a huge planner when it comes to vacations, booking everything in advance, planning itineraries, researching all the must-sees and must-dos. It was kind of freeing to just go, and leave all the planning to someone else!

Like I said, the absolutely best part was the time with my daughter — but the whole experience really was wonderful. Yes, you need to be open and willing to leave your destination in someone else’s hands… but it’s just so much fun. If you’re willing to get out there and take a chance, this is a great way to go!

30 thoughts on “The surprising joy of surprise travel

  1. I love the whole idea of a surprise trip, and it sounds like you had an amazing time! I’ve only passed through Denver but I would love to get back. Now I’m scheming how I could do this with my mom (or husband!), hehe. Thanks for posting this!

    • You’re welcome! I hope you convince someone to give this a try with you! We’re already talking about trying to do another surprise weekend in the fall, and another friend of mine just got super excited about it too. 🙂

    • It really was a treat! It sounded crazy when I first heard about it — but there really was something great about keeping it a surprise until the day of departure and heading out with an open mind.

  2. Wow, this sounds so exciting! I’d be down to do something like this, but my mum wouldn’t she likes to know where we’re going and what we’re doing. So it’s a good thing our trip this weekend to Atlanta is all planned and our activities pretty much booked- so I’m excited!
    I’m glad to hear you had a great time! 🙂

  3. This is so cool! One of my students and her mother also did one of these Pack Up & Go tours last year and I was jealous! I wonder where they’d send me?? 🙂
    I’m so glad you enjoyed Denver – Colorado native here – born and raised – can’t imagine living anywhere else!! It is so cool to hear about where they sent you. I particularly adore our Botanic Gardens…. but there is PLENTY more where that came from. I hope you come back! 🙂
    Great post – thanks for sharing your adventure!!

  4. This sounds like so much fun. They used to do ‘mystery flights’ in Australia but it’s been years since they’ve run them – same concept except just flights and just for the day so quite different to your comprehensive experience!

    • Mystery flights sound awesome! It’s funny because I’m usually such a planner, but the secret destination aspect and just going wherever they sent us made this such a great experience.

  5. This week I went on a surprise trip to New York! SO thrilling and SO much to write about! Thanks for your post, Lisa.

      • That’s so awesome! If you are interested in history and fashion, I highly recommend checking out the Heavenly Bodies exhibit at the MET. It was amazing to see!

  6. Oh I love this idea to do as a mother daughter trip… I may have to convince my mother to do one with me as well! Have you been anywhere else with them? Really looked like you had so much fun in Denver!

    • It was amazing! You can check them out on Facebook to see more of their clients’ trips — so many amazing adventures! I haven’t traveled with them anywhere else… yet! I definitely would go again!

  7. I love this idea!! I knew some friends that used to go to the airport on new years eve and book the first plane to spend 1st of January in a different place everytime ! I really love what you did and I think it makes you visitplaces you wouldn’t go to in the first place 😊

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