As I’ve built my travel content business over the past 13 years, one thing has become clear: I adore the act of traveling to new places and I love writing about it when I get home, but the actual planning? I just don’t love the research phase like I used to. As a matter of fact, I’ve grown to dread it, especially when it comes to planning non-work-related travel.
I get so bogged down in the nitty gritty details, by the time Rick and I decide on a vacation destination (like pulling teeth for my easygoing Enneagram 9 husband), book flights with some combination of miles and actual dollars, read umpteen hotel reviews and try to find the best fishing guide, I’ve spent a week’s worth of working hours in search of R&R. It doesn’t add up!
Putting in enormous effort, time and stress in search of relaxation seems like the wrong answer to the question.
So what is the answer? How do you have an amazing trip with thoughtful, personalized details AND skip all the stress and actually enjoy the experience once you get there?
What is Surprise Travel?
Surprise travel, a concept integrating the expertise of a travel agent and the element of surprise in that they choose a destination for you, intrigued me. Technically it takes all the planning off your shoulders, but as a bit of an overachiever (read: control freak) in the travel department, I wasn’t sure I could ever let someone else completely take the reigns.
It’s one reason I haven’t utilized travel agents more often. I travel so often that I’m very particular about details, so I couldn’t imagine someone else doing as a good a job as I could. “I’ll just do it myself,” is a personal mantra. (And not always the best way to live!)
All that to say, I’ve been following Whisked Away, one such surprise travel agency for a few years. When the thought of planning one more trip in 2019 was more than I could handle, founder Charlotte McGhee stepped in, and we signed up for our first surprise travel experience.
As God is my witness, I will never be the same.
Planning a Surprise Trip with Whisked Away
Once we decided to take the plunge, we had 10 minutes of work to do before turning all the decisions over to Charlotte.
- First, you choose your region and dates. We chose North America in November, but the world is your oyster. Always wanted to visit Europe’s Christmas markets in the winter or Canada during summer vacation? Everywhere is within the realm of possibility.
- Next, you fill out a questionnaire to help Charlotte curate a personalized surprise trip. It’s easy and almost unbelievably quick.
- WHAT: For Rick and me, we wrote that we like being outside, exploring, animals, theme parks, food… we can have fun in a cardboard box as long as we’re together, so we didn’t have too many requirements or must-have travel needs. More importantly, there’s space to list things that you definitely aren’t into, so I added horse-based activities, anything with bicycles, jumping off things and dolphin swimming/elephant riding. If there are specific activities, hotel brands, airlines or whatnot that don’t float your boat, all you have to do is let Charlotte know and she’ll sort you out.
- WHERE: You also can share if you prefer cold or warm weather – we indicated either because again, we just love going places together, but if you’re itching for somewhere balmy and beachy or snowy and snuggly, you can definitely specify. I loved that there was a place to list destinations you 100% don’t want to visit, so I listed New York City and Atlanta, because I lived there, and places like Chicago, the Florida Keys and the Finger Lakes because we’ve been there pretty recently and didn’t want to destination double dip.
- Last step, wait for your envelope filled with trip details to arrive!
Seriously…. that was it. It’s the least amount of time I’ve spent planning any trip in my entire career as a professional travel expert. I was equal parts nervous and thrilled.
Surprise Trip Reveal
Trying to guess our destination became the topic of every date night for months. We analyzed possibilities, pulled up maps, made strategic guesses and changed them 100 times. What about a spa trip to Arizona? Foodie fun in the Pacific Northwest? Leaf peeping in New England?
All the wondering made the lead up to the trip that much more fun, which came as yet another surprise within a surprise in this travel experiment.
Charlotte sends helpful emails in advance of the trip, including one with details on departure time, suggestions on what to pack and a weather forecast about two weeks out. The big envelope with flight information, accommodations and activities arrives in the mail a week from departure.
I kid you not, that envelope stared me down all week.
I have very rarely been surprised by anything in my life… not a surprise party, not a marriage proposal, not even birthday gifts most of the time. So even though I desperately wanted to open the package so I could plan every outfit and make sure I had all the right shoes and camera gear, I decided to enjoy this rare opportunity to experience real surprise and wait until we arrived at the airport to open the envelope.
It drove me half crazy, y’all.
Everyone was asking us where we were going. It was B A N A N A S to say, “I have no idea!” even on the day of the trip.
We arrived extra early at JAX (I just couldn’t wait at home any more!) and tore into our Whisked Away packet. It might sound cliche, but I really felt like a little kid on Christmas morning.
We got San Diego!
Cue a neverending slew of Anchorman jokes…
Rick actually guessed San Diego based on the weather report, that smart little cookie. He’s never been to California and I haven’t been in ages, so we were both thrilled with Charlotte’s destination pick for us.
Up next: we checked in and hopped on a flight. No hemming and hawing over details, choosing departure times and fussing over seat selections. We just followed all the neatly included instructions and like that, we were on vacay.
And we had the whole flight to read through our personalized booklet filled with details.
Charlotte truly has the Midas touch as every detail of our trip was curated specifically for us. Not for nothing, but it’s pretty challenging to impress someone who travels for a living, but Charlotte crushed it. I was delighted with every detail, from our centrally located, two-story luxury houseboat (with massage chair!) in the harbor to our sunset sailing and rescue dog experiences.
We had the right balance between free time and scheduled activities, a curated list of nearby restaurants to choose from and suggestions on how to spend our time in San Diego.
It wasn’t just a list of things to do, it was a sensible itinerary with centrally located accommodations and 100% spot-on recommendations. I also loved that there’s more than one surprise along the way, including thoughtful communications and mailers. It was really a well put-together experience that starts at sign up and didn’t end until we got home.
Like… how have I never done this before and how am I ever going to go back to planning my own vacations?
Whisked Away Surprise Travel FAQ
Instagram followers asked me a ton of questions, so I’ll answer a few common ones here. But for a more thorough list of questions, check out ExploreWhiskedAway.com.
How long are the trips?
You can choose your length but most Whisked Away customers book 1-2 weeks of travel.
How much does it cost?
You decide on a total budget and 20 percent of it goes toward planning.
How do you know what to pack?
Charlotte sends a suggested packing list, based on weather and planned activities, about two weeks from departure. I was moderately concerned about this but we had everything we needed based on her suggestions.
Where can you go? Is it US only?
No! Charlotte sends people all over the place. Recent Whisked Away travelers have visited Aruba, Prague, Ireland, Paris, Sedona, Costa Rica and beyond.
What if they send you somewhere terrible?
First of all, I’m convinced everywhere in the world has something interesting to offer, so if you can’t find it, maybe there’s a deeper issue. But Charlotte loves travel and is running a business, so I can’t imagine you’d have to worry about that!
Who is Whisked Away Surprise Travel For?
Charlotte will be the first to tell you that surprise travel is not for everyone, but having now been through the process, I have some thoughts.
- If you’re a busy, overwhelmed, Type A, control freak or even all of that AND a detail-oriented travel expert like me, I assure you, you are in the safest hands with Charlotte.
- And if you’re more like Rick and you struggle to plan trips because you’re indecisive or just not sure where to go in this whole wide world, Whisked Away is a great option. It takes all the decisions away and leaves you with an adventure. What could be better than that?
Couples, friends, solo travelers – I can’t imagine a person who wouldn’t benefit from the convenience of a Whisked Away trip. They even do surprise honeymoons, a concept I love and wish was available when Rick and I ended up at a vanilla all-inclusive because we were just too tired from wedding planning to coordinate anything extravagant.
And this may blow your mind, because I am always problem solving and coming up with ways to improve EVERYTHING, but I don’t have a single complaint or even one helpful suggestion. Our trip was flawless. Our flights, accommodations and activities were better than what we would’ve even chosen for ourselves, and our packet was customized to us, filled with incredible restaurant recommendations and all the info we needed for the most carefree adventure we’ve ever had as a couple. It could not have been better if we planned it ourselves.
And the fact that it took 10 minutes of my time to fill out the survey and turn it over to Charlotte is unfathomable.
Intrigued about surprise travel? Here’s how to connect with Charlotte at Whisked Away:
- Sign up for the Whisked Away email. It’s filled with helpful travel tips and you’ll be the first to find out about specials and promotions.
- Follow Whisked Away on Instagram and Facebook.
PIN ME FOR LATER
Thank you to Charlotte and Whisked Away for planning a truly perfect trip to San Diego, and for making us feel like little kids waiting for Santa. We are fans for life!
