Last Updated on December 17, 2023 by Marybeth
It seems people fall into two distinct camps: they either love surprises, or they loathe surprises with such a fervor you’d better look out if you ever try to pop one on them. I have friends who light up like sunshine when completely startled, out of the blue – them wearing no makeup and twenty-year-old sweatpants – when assailed with something totally unexpected. Why is that fun?
As a travel blogger who feels actual bliss researching, plotting, and planning a trip (I know: I’m weird) choosing to go on a surprise trip that someone else had curated pulled my oh-so-stubborn self out of a happy place I’ve comfortably rested in for ten years. Biggest surprise of all: I loved it.
Guess Where Trips offers one-day, surprise, self-guided road trips that you can purchase as a delightfully designed package mailed to you (it’s amazing, I highly recommend this mode of receiving your trip: that tactile feel of handling high quality, four-color printed materials) or a PDF digital version sent to your inbox. The Guess Where Trips team has elevated the day trip to a luxury-feel art of exploration. With my background in graphic design I found the packaging, the high quality paper stock, the visuals, and just the element of yes, surprise, to be outstanding. A Guess Where Trip will make the perfect gift for your travel-loving adventurous friend / mom / husband / teenager / dad / or those Happy Hour sidekicks.
Imagine setting off, not knowing where you’re going exactly (but you do have a clue; when you choose your trip you choose your preferred geographical area for the day) and your travel partner gets the excitement of opening all the gorgeous materials and finding out your first stop of the day. Or better yet, have them drive so your day unfolds slowly and deliciously in your hands! Trips are recommended for 1-5 people, so bring your bestie or your crew.
You’ll hold this lovely box in your hands that was wrapped in cotton twill ribbon, and when opened you’ll find artsy tissue paper with a sticker “Surprise Inside.” Each step of your unboxing is photo-worthy (do it!) Inside is a perfectly sized sage green kit folder to hold all your travel info, which includes five envelopes, each with a booklet describing each step of your day. Starting with Before You Go, which covers all your FAQs and then some, and four more for our Treasure Coast Explorer trip. Without giving much away – though I’m dying to tell you ALL about our trip – our instruction booklets were:
An Island Morning (which may have included a delicious breakfast overlooking the ocean.)
Beach Town or Birding? (shopping and food were our choices!)
Boardwalk Bliss (we went to all three recommended restaurants in this town!)
Choose Your Own Adventure
The epic beauty of taking this adventure that is planned for you (meticulously researched, creatively arranged) is that you can decide what parts of the trip you’d like to experience. Do it all! Or select your stops according to what you like to do best. Our Choose Your Own Adventure gave a number of recommendations to pick from, including a hiking option, a history option, a garden option, and a restaurant option. Other stops had a birding option, a museum option, photo ops, “if you brought your kids,” and “if you brought your dog.”
A separate box holds “A Gift for You,” a practical and fun item you’ll use again and again.
Maps are included, which I found to be super helpful as we didn’t have to be grabbing our phones and trying to swipe and zoom around on them. Guess Where Trips has included so much helpful information that I’d be here all day describing it to you, but just know that all the bases are covered. Pet friendly, family friendly, activity level, accessibility, and when to go are just some of the need-to-know details they’ve included for you.
Visit Guess Where Trips to explore where you’d like to go, no planning on your part required! You can browse the trips list by map, or take their quiz to help narrow down your options. You’ll find everything from Rural Road Trips, Wineries and Breweries, Views and Secret Stops, Weird and Wonderful Things, Quaint Corners, Wacky Wonders, Film & Food Crawl, and way more.
Guess Where Trips is currently offering trips in Canada, North Carolina, Georgia, and Florida. Coming soon will be trips in Virginia and the Baltimore/DC area. Guess Where Trips in Florida, at the time of publication, are:
Old Florida Trail – Can depart from Gainesville / Orlando / Jacksonville
Mysterious Gems – Can depart from Orlando / Jacksonville
Treasure Coast Explorer – Can depart from West Palm Beach / Miami / Fort Lauderdale
Outback Oasis – Can depart from Miami – Fort Lauderdale / Naples
Adventure in the Glades – Can depart from Miami / Fort Lauderdale / Naples
Make note that the Can depart from areas listed on the website are a general suggestion, and each trip is accessible to more than just the towns noted. For instance, we departed for the Treasure Coast Explorer from the Melbourne Beach area, so our drive there was approximately an hour and a half. During which we two longtime friends attempted to get “all caught up” …. Does that ever happen for close girlfriends??
“If your brain doesn’t know what’s around the corner, it can’t keep you out of harm’s way.” (Psychotherapist Bryan Robinson, Psychology Today.) One reason why people like me hate surprises! After so many years of being convinced that I am my best planner, keeping me “out of harm’s way” (I guess!) I am now a total and proud convert to letting someone else guide me around that corner. Thank you Guess Where Trips! Currently planning – no, oops, deciding, where we’ll take our next Florida Guess Where road trip!
Our Guess Where Trip was complimentary but our opinions are all our own, as always. I wrestle, these days, with reminding myself that just because I’m getting old I don’t need to be cranky and close-minded! Someone else can do just as good a job planning a trip! I’m grateful for this eye-opener about my stubborn self. I was going to use #notjealousatall but I kind of am. Great job, Guess Where Trips! I wish I’d thought of this!
