Not long ago I was enjoying a Happy Hour libation with a couple of colleagues at one of our favorite local bars, the aptly named World of Beer. You’ve heard all about the adventures I’ve had with my extended family of videographers and talents as we traipsed across the globe, but I’m equally lucky to have an exceptional group of women to work with at Miles HQ in Sarasota. Smart, funny and sincerely passionate about what we do, we get together monthly to talk shop and share a few laughs.
On this recent outing, the subject of solo travel came up. Within the group, a few of us had ventured off on our own and one of us was contemplating a solo trip but was expressing some trepidation. It’s true that the thought of traveling alone could sound like a lonely, scary endeavor. Those were definitely my concerns the first time I decided to spend a weekend away in a new place by myself, but that experience taught me an incredible amount about not only the destination but myself.
I was single, no friends were available for travel, and rather than miss out on the opportunity, I decided to go it alone.
Chicago had always been on my list of places to see and the opportunity to visit came at an ideal time. I had recently undergone a major life event (divorce) and needed to escape for a weekend. I was single, no friends were available for travel, and rather than miss out on the opportunity, I decided to go it alone.
Armed with Devil in the White City and a good set of sneakers, I set out for the Windy City for a weekend away in September. I’m a travel busy-body. I wear people out on vacations with my insistence on cramming a great deal into every day (I blame my hectic video production shoot days for that). I also tend to eat my way through a destination and obsessively consult Urban Spoon and Trip Advisor for recommendations. Here’s what my Chicago solo itinerary looked like:
Day 1 (Friday night)
After arriving at my hotel (located near the House of Blues), I took a short cat nap before grabbing a bite to eat at Harry Caray’s. Sitting at the bar, I chatted with another solo traveler seated beside me in between bites of a luxurious vodka tomato alfredo. Calories be damned—I intended to burn off all of them with the several-block trek up to Second City to catch the late show.
Day 2 (Saturday)
Up at 6am, it just so happened that City Running Tours was hosting a 5K running tour of “Tragic Chicago Events” and I was in training for a half marathon, killing two birds with one stone! After my extremely informative run, I had lunch at a nearby Indian restaurant, with my kindle as my company, before catching an architectural boat tour. Martini in one hand, camera in the other, an afternoon spent cruising the waterways and nerding out on architecture was perfection.
After the requisite walk to Navy Pier for a couple of selfies, I headed back to the hotel for yet another delicious nap (what can I say, this girl loves a good nap). Low and behold, the river had transformed into a Hollywood movie set and I had to take the long way around to get back to my hotel, not that I minded, as my entire day had been filled with happenstance.
A late dinner at Tavern on Rush—such a popular spot that there was only bar seating available, which was where I wanted to sit anyway—included people watching, more reading, a lychee martini and an incredible sea bass before heading across the street for a nightcap at The Whiskey. There I befriended a couple of business travelers before cabbing it back to the hotel.
While it might not seem like a lot, my short solo weekend away was filled to the brim with unexpected discoveries and personally crafted adventures that I’m certain wouldn’t have transpired in the same way had I not been there alone… and I can’t wait to do it again. But, if my story hasn't convinced you, perhaps Buzzfeed can lend some credibility.