Best Travel Experiences of 2025

This year was unfortunately light on travel. I still got in about six or seven trips but I didn’t quite have some of the inspirational bangers that I’ve had in the past. And in some cases, I had some challenging times on the road (see writing an entire Playmaker article in the Pittsburgh Airport.) However, there’s always good times on the road. That’s why I love to travel so much. Below are four moments that defined what I love about travel, gave me a reprieve from challenging times, and drove a smile from my determined face.

Pretty Much My Entire Chicago Trip: This was my best experience of the year. In late April, as Chicago was escaping the clutches of another brutal winter, I flew up there for my first visit. It was a planned trip with my childhood friend, John and his wife, Janice. Janice was up there for a team meeting and John needed someone to urban explore with.

Pretty much from start to finish this trip was awesome. It started with an architectural tour of the city via the Chicago River. I geek out on urban architecture and Chicago has some of the most influential design in the world. As we glide through from building to building, we learned how the city was built, drink beers, and let momentum build for a great trip. 

Next, we headed down to the beach on Lake Michigan. As I mentioned, we were there during what was likely the first warm week in some time so Lake Michigan might as well have been Clearwater Beach. There was an overwhelming amount of 20-somethings sunbathing, playing beach volleyball, flirting, and flossing. 

The next day started with Italian beef sandwiches (best meal of the trip) and a ton of urban exploring. Chicago is one of the most walkable cities in the country. Especially on the northside, where we spent most of our time. John and I walked for a large portion of the afternoon around million-dollar brownstones and the fancy jewelry stores of the Magnificent Mile. We talked about what lies ahead of us in life, gave thanks for the blessing of having, and stopped in for a drink here and there. Then we hopped on scooters and weaved through Chicago traffic to check out Lincoln Park. This was the type experience that’s slightly harrowing but also makes you feel connected, like on the ground connected, to a big city. It was beautiful and fun and strong and way cheaper than those city bus tours. 

The last night I was there, I went out on the town (you knew I was going to check out the nightlife) and I got a chance to meet a few locals. I encountered a couple of supremely confident and self-assured young women (a noticeable trait of Chicago women), hanging out on their own at a place called Stop and Drink and The Berghoff. I learned about tattoos and teaching art and design. I drank quite possibly the nastiest and most potent shot I’ve had in decades (Jeppson's Malört), and I flirted the night away. 

I did feel gnarly the next day but I had a tremendous time laughing, catching up, figuring out how to do more travel like this, and eating tremendously good food in one of America’s world capitals. 

Going to the College Football Kickoff Games in Atlanta: This was the ultimate guys football trip with a few nice little bonuses. My buddy Kenny has discerning taste so he chose to pick up club seats for the first game (Tenn. vs. Syracuse) and I’m here to report that I don’t think I can ever go back. There are levels to club experience and I think it’s different depending on what stadium you are in (I’ll report back and let you know about Benchmark in a couple of weeks), but the club experience at Mercedes Benz Stadium is close to the top. Depending on what package you buy into, you get carving stations, a myriad of food options (including ridiculously good cookies), an open bar, and field access (football players are very tall). It was an incredible and an incredibly luxurious time. So much so that Kenny decided to buy tickets at the last minute for the South Carolina vs. VaTech game the next day. So balled out then as well. 

Unless you’re tailgating (kinda regret not doing that, next year), the place to pre-game is McCormick and Schimicks (now closed, unfortunately). It’s the closest bar to the stadium, they (had) cheap, good food deals, and a great staff. This place gets beyond packed pre-game but we’re able to make friends throughout the time, including a love mother/daughter duo from Columbia that drove in for the game. 

Other items of note:

• If you ever want to get a feel for the heartbeat of a city (and you’re not in a hurry), take the train for a long distance. I stayed in Decatur Square this time around, which is about 25 minutes from the stadium. Because of the distance covered, you see every type, demographic, and socioeconomic of people- from single moms to bros to brahs to the guy who played hip hop on his bluetooth loud enough to here it from several train cars. 
• I forgot how cool Decatur Square was, although, I probably won’t stay that far out again. Great shops. Cool and interesting bars, including a tiki bar with traditional island drinks. Also, a couple of really cool breweries. 

The Somebody Feed Phil Mini-Food Tour of Orlando: The mark of a great travel show is when they can uncover hidden gems and inspire people to go to these places. A few years ago, Phil Rosenthal visited the Orlando area and highlighted its diversity of cultures and how that’s reflected in the food scene. For some people this is a long trip and for some people this feels like a lame idea, but for me, Orlando is quite accessible and it was formerly my home for four and half years. I know where to stay that feels authentic and cool. Luckily, many of the places highlighted in the episode are clustered in the same part of town. 

I dropped my bags off at my lovely little Airbnb in Colonialtown, a historic neighborhood in the northern part of Orlando and immediately caught an uber to Crocante Restaurant. Crocante is a high-end Puerto Rican restaurant that serves unbelievable food and cocktails. I got the pancetta sandwich. The salsa verde gave it a full, sorta sweet-salty flavor, and there’s a great, and slightly unexpected crunch that comes from the chicharons. It’s also a very meaty and filling sandwich. 

The next day I headed up to Domu to try their famous wings. They did not disappoint. Domu wings have a crispy sesame seed coating that provides a nice hearty crunch, but that’s not what makes these wings special. They use substance called kimchi butter that gives the wings this deliciously tangy and salty (I like salt) flavor that makes them phenomenal. Plus, they’re just crunchy enough, and just meaty enough. You know what I mean. 

On my next trip, I hope to visit Gideon’s Bakehouse, which was around the corner from Domu but had like a 50+ deep line, and Kook’N with Kim, an Eatonville institution. I also want to try Bahn Mi Boy. Damn, I love Bahn Mi!

Hanging at Reunion Resort with the Fam: Last, but certainly not least. For my daughter’s birthday, we spent a weekend at Reunion Resort in Orlando. What made this trip special is that while most of my trips are super active, this one was not. And that was the beauty of it. 

When we got to the resort, it was already dark and a little cool outside for the pool. Instead, we took advantage of their food hall area and chose a brew pup and partake of some delicious burgers and beers (Harper had lemonade). 

The next day after picking up breakfast for the fam and items needed for the pool, we went down and lounged, hard. We found a shady spot to park our towels and cooler, not easy to find on an unseasonably hot day and just relaxed, talked, people-watched, consumed tropical beverages, and occasionally cooled down in the water. We also talked with several families while there, which is always fun to do when on vacation.

And then when we were down right pruny, we went inside, dried off and went to a cruise-like buffet area off the pool for dinner. Aside from eating great pizza in one of the foodie spots around the world, two scenarios are built for pizza, late drunken nights and family vacations when you’re feeling lazy and don’t want a sit down dinner. We crushed that pizza y'all. And then we followed it up with some ice cream. Not the best gastrointestinal choice, but deeply satisfying at the time. 

The next day, which was actually Harper’s birthday, we headed back and found our way to Plant City for some strawberry treats before reaching our final stop, The Sugar Factory. Always a loud and festive time, the Sugar Factory, provided overpriced, but tasty treats and it made my baby happy. 

I think the underlining theme around all of these times was that they involved great people. Last year was one of my toughest, but these little trips got me through it. Travel can be a lot of things for me. Last year, it was therapy and an opportunity for sweet connection.