As the founder of Pack Up + Go, most people assume that I’ve taken several of our trips.

Until just a few weeks ago, I was embarrassed to say that I had not, in fact, ever gone on a Surprise Vacation myself. It took me six years, but I finally went on a Pack Up + Go trip! My only regret? Not doing it sooner!

Written by Lillian Rafson

Why I Decided to Pack Up + Go

If I had to sum up my experience traveling with Pack Up + Go in one word, it would be carefree. I started Pack Up + Go after the most carefree summer of my entire life - I was backpacking solo around a region I knew nothing about and every day felt like a completely new adventure. I never knew where I would end up, who I would meet, what I would see, do, or eat. It was a life-changing experience, and I remember never having felt truly carefree in my entire life. Then, I started a company. Suddenly, I had a lot on my mind all the time. It felt like my carefree summer evaporated overnight. I would never trade the experience of building and running Pack Up + Go for anything, but throughout the years, I have wondered what does it actually feel like to take one of our trips?

My partner and I decided to take a Plane Trip for three nights. We take a lot of road trips but decided it would be fun to get on an airplane and make this a truly relaxing, romantic weekend getaway. It was such a unique and exciting experience completing the Pre-Trip Survey together, thinking through all the things we love to do when we travel, and verbalizing it for others to use to plan our trip! We were sure to call out that we love food + drinks, sightseeing, and outdoor activities. We’re the type of people who like to do a lot of things, especially when we travel! We submitted our Pre-Trip Survey, and the anticipation kicked in.

I found myself thinking about the trip constantly but in no specific terms. In the shower, in the grocery store, walking my dog, or in the car, I would start to list out possible destinations in my mind. But, I told myself, when I get the weather forecast for our destination, I’ll obviously be able to figure out where we’re going.

Preparing for My Trip

So, a week before our trip, I was eager to open our One Week Until Departure email to finally put this mystery to rest. But as I closed my inbox I felt more proud than ever. My team had managed to really, truly surprise me.

I love packing for trips, and I take pride in the fact that I’m an easy, light packer. I have a TravelPro carry-on suitcase that I love, and I’m always careful to only pack things that I know I’ll definitely wear. Nike sneakers for exploring ✔️, North Face jacket ✔️, Fabletics for comfort on the plane ✔️, a couple of basics for exploring by day, and a couple of items for evenings out. For skincare, I pack light and just use the essentials - L’Occitane moisturizer and my favorite Sunday Riley face oil. Voila.

I'm Heading To...

The morning of our departure, we were excited. There was so much anticipation, but no expectation. We knew that no matter where we ended up going, we would have a great time. Based on the weather forecast and packing tips, my final guess was Seattle. We arrived at the airport around 6AM, and at long last, I had the experience I had dreamt of for six years - I opened my Surprise Envelope on my very first Pack Up + Go trip.

Charleston!

Almost immediately, I felt carefree. We sat at the airport and flipped through our curated recommendations, hotel information, and fun facts about Charleston provided by Pack Up + Go. It felt like, for the first time, I could travel and actually relax. Everything felt easy and exciting. The pre-planned activities lined up for us were perfect. The dinner reservations for our first night meant that we didn’t have to stress about where to go last minute.

Pack Up + Go reserved us a room at The Charleston Place, a gorgeous hotel right in the heart of the historic district. It was the perfect place to stay for a romantic weekend getaway, and the service could not have been better. The room was classic and timeless, and the hotel had a beautiful pool and hot tub. When I book my own accommodation, I usually go for the simplest option, and I was shocked how staying in such a beautiful hotel set the stage for a great vacation and made us feel like royalty.

As we strolled through the streets of Charleston, we located many small businesses that were featured on our recommendations, including a charming bookstore that featured rare books, which my boyfriend had stated he loves on the Pre-Trip Survey! It was pretty chilly during our Surprise Trip, but this didn’t phase us at all - we were too excited about exploring the city and checking out the recommendations Pack Up + Go provided, so we added an extra layer and kept exploring! To warm up and relax for the afternoon, we went back to the hotel and took advantage of the beautiful pool. Sitting in the hot tub, I realized that every single time I’ve traveled and stayed in a hotel with a pool, I’ve always been so focused on cramming in seeing everything and doing everything I possibly can, and I don’t think I’ve ever actually just relaxed and enjoyed the amenity. Next, we mapped out a self-guided food tour to check out all of the hotspots that Pack Up + Go recommended. We snagged bar seats at award-winning FIG, got cocktails at Doar Bros., and had an incredible meal at Lenoir. My biggest complaint was simply that I couldn’t make more room in my stomach for more food.

The next morning, we woke up to bright blue skies and brisk weather. Happily, this meant we had some of Charleston’s top sites to ourselves! Rainbow Row, which is usually crawling with tourists, was empty. The Battery had only a handful of locals on their morning stroll. The wait for breakfast at Millers All Day was a fraction of what it would normally be. In the afternoon, we found an opportunity to grab a coffee in a charming cafe and read our books for a few hours while enjoying delicious pastries. A few free hours after that, we found last-minute availability for massages! I could finally feel myself remembering what it felt like to truly be carefree.

What I Learned…

Departing on my own Pack Up + Go trip helped me understand that I’ve become a different type of traveler when I plan my own trips now. I go into my vacations with a clear to-do list of things I want to see, eat, take pictures of, and experience. I usually line up meetings for work and imagine how our travelers would enjoy a destination and try to cram in as much as possible so I can test it out for Pack Up + Go trips. It surprised me to remember how it felt to really just go with the flow, keep an open mind, and treat everything that happens on a vacation like a gift. Both my boyfriend and I are the types of people who like to do a lot of things all the time, and the ability for us to truly unwind, relax, and experience the thrill of a surprise together was truly nothing short of a joy.

Would I go on another surprise vacation with Pack Up + Go?

Absolutely.

Now that I know how the experience feels firsthand, I completely understand why we have so many repeat travelers. There aren’t many genuine surprises built into our day-to-day, and this experience allowed us to reconnect with each other, create shared memories, and truly just enjoy each other’s company. I would love to go on another romantic getaway, but would also love to share this experience with my best friends on a girls' trip, my siblings for a family trip, and myself on a solo adventure. Until my next Pack Up + Go getaway, I’ll just have to incorporate more spontaneity in my life and remind myself to embrace a carefree mindset. 

Ready for your next adventure? Book a Surprise Trip with Pack Up + Go today!

Want to hear more? Check out Lillian + Kenny on Envelope to Exploration, a podcast by Pack Up + Go!