Expedition 9 to 5

Very few people end up going to high school with their lifelong friends. Even fewer people end up moving in the middle of high school and finding their lifelong friends. Lucky for me, I did just that. The 4 of us hail from the little town of Darien, Illinois, in the southwest suburbs of Chicago, where I magically worked my way into a friend group that was years in the making. Along with the excruciatingly embarrassing memories that come with every high school experience, mine came with 3 girls who would travel states, oceans, and countries to see one another. 

Before this trip, we mainly visited each other in our respective cities of Austin, DC, Raleigh, and New York City. This was the first trip post-grad where we would not be squeezing into one of our apartments (an exhilarating step in adulthood!). Thanks to the generous gift from Greg Kilrea, we were able to do this trip through Pack Up and Go! 

Pack Up and Go is a company dedicated to crafting your perfect getaway. They specialize in curating trips that are a complete surprise, orchestrating your destination and the experiences that await you. To say the folks planning our trip had a complicated task is an understatement. They were in charge of planning a weekend-long girls’ trip with departures from 4 different cities. To make matters more complicated, an additional 6 cities were excluded based on recent trips the 4 of us had taken, AND they had to choose a location where we could all take direct flights to maximize the time we spent together. The Pack Up and Go team did not let us down. The surprise trip location was (drum roll please) Miami! Somehow they picked a city that none of us had been to and a perfect destination for the girls’ trip to commence. 

How it worked:

Months before:

When filling out the Pack Up and Go survey, you are faced with many options on how to tailor your trip. Do you like activities? Do you like structure? Are you go with the flow? What kind of travel do you enjoy most? How much are you willing to spend? They take all of this information into account when planning your trip. We started by providing which airport we would each be leaving from, then supplied our TSA precheck numbers, and checked yes on eating, drinking, and exploring whatever city they sent us to. We submitted with nervous excitement and a slight fear that we may accidentally end up back in the Midwest. 

1 week before: 

A week before our departure date, we were sent an email with a weather report, a brief description of what we could expect from our trip, a list of suggested items we may want to pack, and what time each of us would depart from our respective airports. Based on the 3 days straight of sunshine and chance of light showers, we had assumed it would be in Florida or a beach town, but the Pack Up and Go folks really threw us off with the mention of this destination being a “casual city.” During this week, we were also sent our surprise packet, including our flight information, where we were staying, planned activities, and other recommendations. This envelope is labeled very well, telling you not to peek inside until the day of your destination. It sat on my vanity for a whole week, screaming at me to open it. I thought I could get away with holding the back of the envelope to the sun, but that was also covered with a “no peeking” sign. Pure torture. 

The night before: 

In true friend group fashion, we decided to make a bet on where we would be surprise-tripping. Each member got 2 guesses- one serious and one outlandish (mine were Scottsdale, Arizona and Detroit, Michigan). They truly could have sent us to the middle of BFE, and we would’ve made that the most iconic girls’ trip in history, but Erin ended up guessing Miami, and she enjoyed some complimentary drinks on the rest of us.

Pack Up and Go recommends that you open your surprise envelope at the airport on the day of your departure; however, we all wanted to find out our trip location together, so we compromised on a 9 PM CST Facetime the night before to reveal the destination. We were completely thrown off guard when we opened our envelopes to see “Miami” in gorgeous curly cue writing, as our travel agent had described the city as “casual.” Known for its bustling nightlife and club scene, I wouldn’t classify Miami as a casual destination for four 24-year-old girls. I squeezed my heels into my already-packed, over-stuffed bag and called it good. Most of us (excluding a late-night packing Bridget) settled in for our early flights the following day. 

What was planned for us:

The envelope contained instructions for our accommodation: the Kimpton Angler in Miami Beach. This vibrant yet serene hotel was conveniently located within walking or biking distance of all parts of Miami Beach. But, what really sold me on this place was the complimentary wine and sangria every day from 5-6 PM. The envelope outlined 2 dinner reservations made for us at Mama’s Tacos and II Pastaiolo— both excellent places to dine. If you show up for a fun evening at II Pastaiolo, you too, could receive XL espresso martinis in margarita glasses. With our leftover money in the travel budget, The Pack Up and Go team provided us with a $100 Uber gift card that covered almost our entire transportation for the weekend. 

Our itinerary also revealed that we were scheduled for an art deco walking tour on Saturday at 11 AM. This turned out to be a highlight of our trip, as it was an activity we wouldn’t have chosen independently, yet we found ourselves thoroughly enjoying the experience. We strutted (and sweated) through the streets of Miami, learning the city’s history and taking in the brightly colored and uniquely styled buildings. We also happened to be at the Versace Mansion on the 46th anniversary of Giani Versace’s death. Wild coincidence (unless the people at Pack Up and Go know something we don’t?).

In addition to our planned activities, our itinerary outlined different restaurants, activities, and clubs we may be interested in. This was a beneficial list, but we took the rest of the trip into our own hands.

What we planned ourselves: 

We, of course, budgeted time for our own antics. We all landed early Friday morning, used our Uber credit to get to the hotel, dropped off our luggage, and parked it on the beach. After sufficient sun and cocktail consumption, we stumbled back to the hotel (grabbing the free wine on the way in), showered, and let the towel time commence before our first evening out. 

Towel Time, aka TT Definition: The time you take between showering and getting ready to lay in your towel and/or robe. Often used to scroll Tiktok, plan outfits, and recap that day’s activities. Towel time is most fun and effective when partaking with good friends. 

Saturday, we woke up with mild hangovers. Nicole and Erin left to grab breakfast and coffee before our walking tour, while Bridget and I stayed in bed just a little longer. Post breakfast, we strolled to our walking tour with Missy (a true Miami Icon). In addition to a complete Miami history lesson, we soon discovered the commonality of summer daytime rain showers in the city. The afternoon storm was brewing as we finished our tour, and we made it to the delicious Cuban restaurant of Havana Vieja right as it started pouring. After we stuffed ourselves full of Cuban sandwiches and empanadas, we thought it would be the perfect time to return to our swimsuits and head to the beach. The rain had cleared up, and the beach was stunning (and significantly less crowded). I talked Bridget into swimming to the sandbar, embarking on one of those “what’s the grand plan of life” chats, all while bobbing up and down through the waves. Being vertically challenged, I could barely reach the sandbar on my tippy toes while Bridget stood flat-footed. Once we (I) tired of treading, we paddled back to shore, primed for our second night out on the town. I’ll leave the specifics to the reader’s imagination, but I can confidently say that I’ve never experienced anything less than a fantastic night out with the dynamic trio of Bridget, Erin, and Nicole.

We took Sunday in stride, mixing our liquid IVs and doing the most shambly packing job we could muster. Dropping off our luggage at the front desk, we used the day to bike the beach path and head to the most southern point of Miami Beach. After sweating through our clothing on what people may call a “relaxing bike ride,” we capped off our day lounging by the Kimpton Angler rooftop pool. We were soon on to the next adventure: Miami International Airport.

Additional surprise: 

As a last little gift from Miami, she tried to keep us all within the confines of her city with a heinous storm, canceling or delaying all of our flights. Nicole and Erin escaped her clutches Sunday night, while Bridget and I could only get rebooked the next day. Our girl Libby at Pack Up and Go came in clutch and covered our airport hotel for the evening, Bridget ended up buying a new flight for the next day out of Fort Lauderdale, and since I couldn’t get out until 8 PM the next day, I had myself a delightful extra day in Miami. 

What would one do with an extra 24 hours in Miami by their lonesome? I recommend renting a car and heading to Biscayne National Park for a boat ride to some of Florida’s best snorkeling. This was my 15th National Park and the most unexpected. Biscayne National Park is only accessible through water transport, as it is made of 95% water. It is also the only U.S. National Park located within sight of a major metropolitan area, offering an extraordinary blend of urban accessibility and natural wonders. I was able to see a plethora of brightly colored fish, swim around in the crystal clear water, and take a closer look at the mangrove habitats. Curiosity got the best of me, so I ventured a little farther than recommended and was treated to the sight of a barracuda and a nurse shark. While the guides didn’t necessarily appreciate this extra adventure of mine, I hopped up on the boat to see that we had more significant worries. Another classic Florida storm was rolling in. Juan and Stefan were excellent and knowledgeable guides who quickly reacted to the aggressive waves and rain. They brought us safely to Elliot Key to wait out the storm. Upon safe arrival at the park, the Biscayne National Park Institute kindly refunded half the price of the experience as well. You can book my tour here. I capped off my solo day with a Publix sandwich for dinner and booked it back to the airport for my 8 PM flight. By some miracle, I made it back to Austin safely that night. 

Overall, Pack Up and Go was an incredible experience. They put together the ideal itinerary for our girls’ trip and whisked us away to a spot we’ll never forget (although I’m sure we would’ve loved Detroit). What blew me away was how the team went above and beyond to ensure we returned home without a hitch while stuck at the airport. Libby was incredible in guiding us through our choices and working her magic to speed up our journey home. Miami certainly treated us well.

Check out our trip through TikTok: