I first started making travel a priority when I realized at 21 years old I’d never seen the ocean and thought that I should do something about that. I scraped together some cash for an airline ticket, boarded a plane for the first time in a decade, and stayed with a friend on Cape Cod for a few days. I spent the next several years broke but finding ways to travel however I could (thank you to all the folks who let me crash on their couches). Somewhere along the way it started to feel very obvious that I need to continue seeing as much of the world as possible.
For 2018, I had a couple small trips lined up toward the beginning of the year, and a few bigger ones planned for later. When an unexpected trip bridged the gap between some of these, I thought it would be fun to set a little goal to fly every month of 2018. I didn’t set any strict rules to this —I kept it to myself at first, and if money and/or scheduling became a problem I would have just aborted the mission. But, thanks to setting my own work schedule at all four of my jobs, and no longer being totally broke (see: four jobs) I was able to make it happen.
So, at the end of the year, I’ve been reflecting on this random, self-imposed goal I accomplished and wanted to share some of my experiences — both for posterity while it’s all fresh in my head, and in case anyone else can benefit from my recommendations. Generally I use Instagram for the majority of my social media needs but I knew this would have way too many words and photos so I dusted off this account I’ve used only for subscriptions anddd I guess I write on Medium now. Anyway, here’s my recap on a year of travel.
January: Indianapolis, Indiana
Over Christmas, I had made plans with my cousin Michelle to come out and visit her. She’s lived in Indy for a while now so I wanted to go see her apartment & neighborhood, plus just spend some time together outside the holiday madness. Added bonus: flights to Indy were super cheap in the dead of winter (go figure).
Cool stuff I did:
- Explored this gigantic antique market and scored some sweet E.T. glasses!
- Took a day trip to Columbus, IN which is known for its abundance of modern architecture.
- Wandered aimlessly around Indy while my cousin patiently took me to whatever buildings I thought looked cool
- Call up a long distance loved one and plan a weekend with ‘em! This trip was mostly just about hanging with my cousin and we had a great time.
February: Cleveland, Ohio
Another weekend trip where the focus was less about the place and more about the company. I met up with my friend Carly, who lives in Washington DC and last year took in my longterm foster cat, Stork. We wanted to go to a live show of a podcast we both like, and they weren’t touring in either of our cities so we decided to just meet in the middle — Cleveland. As an added bonus, we rented a pet-friendly Airbnb so I got to hang out with Stork too.
Cool stuff I did:
- Reunited with Carly & Stork!
- Went to the historic West Side Market and ate pierogies.
- Played shuffleboard and spent the day walking and eating around the trendy little Ohio City neighborhood.
- Honestly, the weather was frigid during our trip so my exploring was much more limited than usual, but I fell in love with the Guardians of Traffic while driving by them multiple times. If/when I make it back to CLE getting close to these guys is at the top of my list.
- Walk around downtown in Public Square and look at all the pretty old buildings and monuments.
- I feel like Mabel’s BBQ is probably a tourist trap but it was genuinely really tasty so it still gets a mention. (2050 E 4th St, Cleveland OH)
March: Charleston, South Carolina
When I was with Michelle in January, we decided to plan a vacation together. I’ve been really wanting to go to Charleston for years now, so when my cousin said she wanted to go somewhere warm I threw it out as a suggestion. To my delight, she was totally down with the destination and my compiling an obsessively researched Google Map of all the places I wanted to go while we were there. You guys — it did NOT disappoint. I loved it so much and spent the rest of the year recommending it to everyone. It’s East Coast but Deep South, tropical but historical. It’s such a weird but neat place. Go to Charleston.
Cool stuff I did:
- Turns out the last week in March is one of the best times for weather and one of the worst times for flight & hotel pricing. In a last-ditch effort to not blow our whole budget on housing, I booked us a room at the NotSo Hostel. It turned out to be really great, they had plenty of nice private rooms and both locations were in easy walking distance of pretty much anything we wanted to do.
- Stared at SO MUCH beautiful vernacular architecture.
- Learned a lot. There are tons of little museums in Charleston. The standout was the Old Slave Mart Museum, whose location in the 1859 building that was actually used for slave auctions made for an especially powerful & haunting experience.
- Walked through every old graveyard we came across. There are a TON of them with gravesites dating back to the 1600s.
- Gawked at more architecture.
- Ate SO MUCH GOOD FOOD, which I’ll list in my recommendations. For now here’s a picture of us being fools at a delightful gin bar.
- Looked at even more architecture! (I seriously have about 30 pictures on my phone just of every pink building I saw)
- Just wandered around or hung on the porch and enjoyed the nice weather, friendly folks, and beautiful scenery of the city.
- Food: almost everything we ate & drank was superb. Plenty of days we just wandered into a random place and it wound up being delicious. Standouts included Husk (make reservations!), The Gin Joint, CO, and Fuel Cantina.
- Museums: besides the Slave Mart and Old City Jail (which are both must-sees) our first day we happened upon the weird & free Macaulay Museum of Dental History, and we also enjoyed a look into the city’s Revolutionary War history at the Powder Magazine.
- Take a walk through The Battery and Waterfront Park (I saw wild dolphins from the boardwalk here and was so excited I screamed).
- Stroll through the Charleston City Market. It’s touristy but you can just check out the sheds and the Greek Revival front entry building without having to buy any tchotchkies unless you’re into that.
- Truly, just roaming the streets was magical. There are so many beautiful Charleston single houses with flickering gas lanterns out front almost everywhere you go. Gothic churches, art deco theatres, old Georgian mansions… they’ve got it all.
April: New York City, NY
I usually make it out to NYC at least once a year, but this time was kind of a surprise. Very last-minute, my friend/co-worker Niki and I were invited to a fashion shoot that she really wanted to go to. Always down for a trip, I bought a flight the same day. This was the quickest of all my trips this year, only about 36 hours, but I think we packed a decent amount in.
Cool stuff I did:
- Would it shock you if I said, looked at architecture? It’s me, and I’m in New York City. So there was plenty of that.
Ate delicious food, of course. I finally made it to Momofuku!
- Walked the length of the High Line, an old rail track turned public trail.
- Went to the fashion shoot that was the impetus for our trip.
- Had hot dogs and watched model sailboats in Central Park before catching our flight home.
May/June: Boston, Massachusetts
This one actually overlapped from the end of May into the beginning of June (but I still wound up flying twelve times this year so I’m gonna say it all still counts). My partner Matt and I had been talking for a while about how we wanted to go to Boston together, as he lived there briefly and I’d been once before and wanted to see more. So when there were cheap flights when I happened to have time off around my birthday, we jumped on it.
Cool stuff I did:
- Walked up and down the Commonwealth Avenue Mall, which is incredibly beautiful and where I’d want to live if I were a mega rich Bostonian.
- Fed the ducks and squirrels at the gorgeous Boston Public Garden, America’s first public park.
- Explored the historic Back Bay and North End neighborhoods.
- Took a train out to the ‘burbs to visit my dear friend from college, Diggs, and her partner Brendan who took us to a nice little winery.
June/July: New Orleans, Louisiana
The only 2018 trip I had planned far in advance. My roller derby team had a game scheduled down here, and most of us decided to spend extra time vacationing. I was there for almost a week along with about 30 of my teammates and we had an absolute blast. I always knew I needed to see New Orleans, but I was actually surprised by just how much I liked it. It’s full of unique culture, there’s so much to see and do, and also it felt surprisingly livable, rather than just the party town I thought it was. Ever since we got home I’ve been half-joking that we should get a winter apartment down there.
Cool stuff I did:
- Was constantly overwhelmed by all the charming Creole townhouses and shotgun houses everywhere we looked.
- Rode the streetcar, sometimes with a destination and sometimes aimlessly just because I loved it so much. The first time we took it was late at night and when it came rumbling up I cried because it was so magical, in case you wondered what it’s like to be a crazy Train Person.
- Played a fun game of roller derby with a bunch of my favorite humans.
- Explored downtown (is it dumb that I didn’t really realize there were tall buildings in New Orleans?) and the Garden District.
- Go to Preservation Hall and see a jazz show. It was amazing.
- Take the guided tour at the Pharmacy Museum. The speaker was so engaging, it was like a fascinating live-action podcast.
- Trek out to the Tree of Life, if you’re into that kinda thing. It’s really just a big old tree but it was cool to see.
- Have a Ramos Gin Fizz at Bar Tonique. Fair warning: it takes 20 minutes to make, but it’s an experience and it’s tasty.
- Eat at the Court of Two Sisters if you’re up for a fancy-ish meal on a beautiful patio.
August: Detroit, Michigan
I spend a lot of time in Detroit each year since Matt grew up there and we frequently go visit his family. I’ve come to really love it and it’s the only other city that kinda feels like home. We had been kicking around the idea of showing some of our friends around town, and we all finally just picked a date and made it happen. It was a quick 3-day weekend but I feel like we did pretty good as tour guides.
Cool stuff I did:
- Went inside the Guardian Building. Easily the most beautiful skyscraper in Detroit and maybe anywhere.
- Grabbed snacks at Eastern Market. It’s a huge market with all kinds of produce and goods that’s been running for over 150 years. There is also tons of beautiful street art all around the area.
- Went to Belle Isle. A gem of a (massive) waterfront park, complete with a free conservatory and aquarium.
- Went to Michigan Central Station, in use for 75 years but shuttered for the past 30, it’s fallen into disrepair but was recently purchased by Ford with plans for redevelopment.
August: Road trip to Yellowstone National Park, Wyoming
This wasn’t part of my yearly flight goal, but it was still a big journey that I wanted to document. My dad and I took a week-long road trip out to Yellowstone National Park, stopping at plenty of other sites on the way. As you can probably tell, my trips usually revolve around cities and urban life, but it was nice to surround myself with nature for a while.
Cool stuff I did:
- Visited an old abandoned mill in Sioux Falls.
- Listened to Bruce Springsteen at the Badlands.
- Got to enjoy my dad’s excitement at crossing “See Mount Rushmore” off his list of life goals.
- Wound up both enjoying Custer State Park way more than we expected, and spontaneously decided to spend an extra (breathtaking) day there.
- Saw so many buffalo in the wild! Didn’t really get any good shots of them close-up but had a good laugh going through my dad’s millions of blurry phone pictures of brown faraway blobs.
- Did the whole Yellowstone experience, namely lived with no internet and stared at all the crazy stuff the earth does when left to its own devices.
- Saw cute kitschy camp stuff.
- On our very last day, got real ambitious after doing very minimal physical activity and decided to do a crazy hike down the edge of a cliff to go look at a waterfall. Was rewarded by a gorgeous view complete with a rainbow. (Also, I unironically wore a fishing hat almost every day on this trip and really felt like I was owning it even though I probably wasn’t.)
- Kept seeing pretty views all the way home.
- Food on the road is mostly garbage. We sprung for a fancy meal in one of Yellowstone’s supper clubs and it was so worth it just to eat real food and vegetables that weren’t fried.
- We had planned out a whole day at Mount Rushmore but it really wasn’t needed. You look at the monument for a few minutes, peruse the little museum, and you’re pretty much done.
- South Dakota was SO much more beautiful than I anticipated. I think you could easily do a whole vacation there, I could have spent far more time at the Badlands and Custer State Park, and just driving around the mountains of the western half of the state was pretty rad.
September: Denver, Colorado
This was one of those trips where I realized I had a bunch of free airline points and the fates just sort of aligned. I hadn’t seen my buddy Erica & her partner David in a couple years, and they had just moved into their very own house! So I went out (literally the week after they moved, thank you beautiful angels for accommodating me) and spent a couple days hanging out.
Cool stuff I did:
- Poked around their booming downtown.
- Took a day trip up north to a historic and adorable little mountain town to see the beginning of fall colors.
- On a whim, took a ride on what was basically a real-life model train set.
- On another whim, ended up at the Hump! Film Festival.
- Get a drink at the Cruise Room if you also love art deco, prohibition-era cocktail kinda places.
- Eat pupusas & other Salvadoran food wherever you can! I wish we had more pupuserias at home so whenever I’m out west I’m all over it.
- Sounding like a broken record here but for real: take trips to see people you love! Spending a couple day with these folks hangin’ in the backyard shootin’ the breeze was good for my soul.
October: Austin, Texas
One day in May, I found out one of my very favorite bands (Miniature Tigers) were going on tour. I missed them last time they came through Chicago and I was bummed. This time, I eagerly jumped onto their website only to find that their Chicago tour date was a night I already had a wedding booked. So instead, I decided to pick a city I hadn’t been to and see them there and that’s how I wound up in Austin. I was actually on our Boston trip when I decided all this and texted my buddy Fox who grew up in Texas, “Wanna go to Austin in October?” and that’s how I planned a trip while on another trip.
Cool stuff I did:
- Tourist stuff! Poked around all the artsy little shops and restaurants, and went swimming at Barton Springs.
- Scooted everywhere! This was my first time riding the app-based rental scooters and they were a great way to cruise around a new place, slow enough to look around and easy to hop off to explore.
- Finally saw one of my favorite bands perform live, from the front row! Man this was a great show. Big thanks to Fox for going and dancing with me despite not knowing any songs by this band prior to our trip.
- Got friendship ramen tattoos and then went out for ramen.
- Get out into the neighborhoods and scope out all the fun mid-century modern homes that are seemingly everywhere.
- While walking one night we came across Prohibition Creamery, which serves alcoholic ice cream and shakes. We realized this was peak Austin and rolled our eyes but then got drunk on ice cream and it was great.
- Remember you’re still in Texas and brace yourself for MAGA hats.
November: Cincinnati, OH
Okay, this was the one and only trip this year that I made purely out of commitment to monthly flights. I had accrued a smallish amount of airline points by now so I needed somewhere kind of close, and over the summer I met some fun artists from Cincy who were telling me about some of the cool stuff in their city but overall this was pretty random. This was actually the only trip I planned to be totally by myself, but then my mom caught wind and asked if she could join and I said of course.
Cool stuff I did:
- Stayed in Carew Tower, a 1930s art deco beauty filled with great details.
- Walked the length of the Roebling Suspension Bridge which connects Kentucky with Cincinnati and was built by the same man who went on to build the Brooklyn Bridge (with pretty apparent similarities).
- Visited the old Union Terminal, now reimagined as the Cincinnati Museum Center. It was originally built in the 30s and just underwent an impressive restoration project. This is hands down one of my new favorite buildings; I got emotional staring up at the ceiling in the lobby because I’m absurd but wow. My whole trip was worth it just to see this place and its historic preservation is something the people of Cincy should be proud of.
December: Montego Bay, Jamaica
After a long year of work (particularly fall wedding season) I really wanted to go somewhere that I didn’t feel I needed to make a lot of big plans. I usually show up for a trip with a long list of buildings, restaurants, and activities. For this one, I wanted a relaxing vacation. So my friend Minna and I leaned in 100% on the American Tourist vibe and booked an all-inclusive resort in Jamaica. When we came back, besides the usual HILARIOUS jokes about how I don’t look tan, people kept asking me what I did in Jamaica. And I kept telling them, “Literally nothing.” Because seriously, every single day we just alternated swimming, sunbathing, reading, drinking & eating. That was it. And it was fantastic.
Cool stuff I did:
- Flew out of O’Hare for my first time this year, and cackled at how not excited we looked in the photos they took when we entered the country.
- Laid in the sun like we weren’t still going to come home pale and/or burnt.
- Ate jerk chicken every day, and got really excited to drink out of coconuts.
- Uhh, I’ve got nothin’. We kept asking ourselves if we should do more, kept looking at brochures for all these fantastic excursions to see more of the island, and kept deciding that we just wanted to drink rum in the pool all day instead. One day we did go scuba diving and followed a sting ray around for a while, that was rad. But that’s the only thing we did.
- For real though, I really enjoyed the resort we stayed at and would recommend it to anyone looking for this kind of trip. We picked it mostly based on it being ten minutes from the airport but the staff and property were all lovely, and I did learn a bit about Jamaican culture and now really want to go back and see the country properly.
- If you’re in Jamaica and they have Tastee Patties somewhere, you’re in for a real treat.
That’s it! Man, what a year. Thanks to everyone who travelled with me, hosted me, gave me recommendations, or watched my birds while I was gone. I seriously feel so grateful that I get to see so much of the world while I’m young and able. Of course, due mostly to funds the vast majority of my traveling has been within the US and I’m looking to change that soon. I’ve got a wishful European itinerary for 2019 but no solid plans right now. I’m also starting grad school in January so I’m trying to be realistic about how much time that’s going to take up. That being said, when asked the other day if I was going to continue my monthly flights and I said no, Matt asked me “When’s your next scheduled trip?” and my answer was “January 2nd.” So, ya know.
Thanks for reading! And if you ever wanna go on a random adventure, you know who to call.