This week was a road trip in disguise. It started locally with sandwiches, tapas, and an Italian shop in Trumbull, but by Thursday it had turned into a cross-country pilgrimage: Westchester to Jacksonville, a drive into Tallahassee, three nights in a small Georgia town that completely surprised us, my youngest daughter’s graduation from Florida State, and finally a slow drive home through Savannah. Some weeks the food carries the story. This week the story carried the food, and the food showed up exactly when it was needed.
Monday: An Italian Combo at Massimo’s, Then Romanacci Leftovers
Monday started with a quick stop at Italian Corner Deli by Massimo’s in Trumbull for an Italian Combo.
The place itself is great — bright, clean, that proper Italian-deli-meets-pizzeria energy that the Massimo brand has built across Fairfield County. The shop is full of imported goods and pastries that make you want to wander before you order. But the sandwich itself was just okay. The bread and meats were quality, but the build felt a little thin, and an Italian Combo really lives or dies on the layering. I’ll be back — Massimo’s gets too much right not to give it another shot — but this particular combo didn’t quite land.
Dinner was leftovers from the Romanacci takeout we’d had on Sunday, and that pretty much rescued the day. Italian leftovers on a Monday is one of life’s quiet wins. Cold pizza, reheated pasta — it all gets a little better overnight.
📍 Italian Corner Deli by Massimo’s | 6374 Main St, Trumbull, CT ⭐️⭐️⭐️
Tuesday: La Toscana at All’Antico Vinaio
Tuesday took me into the city, and lunch was at All’Antico Vinaio at Brookfield Place.
I went with the La Toscana — salame toscano, pecorino toscano, and truffle honey on their signature schiacciata bread. On paper, it’s exactly the kind of sandwich I should love. Tuscan cured meat, sharp pecorino, the unmistakable hit of truffle honey, all packed into that beautifully chewy, slightly crisp Florentine flatbread.
In practice, this one was just okay for me. The components were good, but the balance felt a touch off — the pecorino seemed to dominate, and the truffle honey didn’t come through the way I wanted it to. All’Antico Vinaio is one of those places I have a lot of respect for, and the schiacciata itself is genuinely special. La Paradiso (mortadella, stracciatella, pistachio cream, pistachio) and a few of their other builds have wowed me. La Toscana, this time, just didn’t.
I’d absolutely go back. Just probably not for this particular sandwich.
Wednesday: Tapas and Drinks at Barcelona
Wednesday was a much-needed evening at Barcelona Wine Bar in Fairfield.
There’s something about Barcelona that just works. The place has that warm tapas-bar energy that pulls you in the second you sit down — the lighting low, the bar busy, the menu wide enough that the table can wander through it without ever ordering the same thing twice. We did the usual — a few tapas, a few drinks — and let the meal unfold the way Barcelona is meant to.
Their charcuterie program is one of the best in the area, the small plates are consistently good, and the wine list is genuinely deep on Spanish varietals. The whole experience has that easy rhythm where you order a couple things, drink a little wine, talk, then order a couple more. By the time you stand up, somehow it’s two hours later.
It was the kind of midweek meal that resets the tempo. Quiet enough to talk, lively enough to feel like an evening out.
📍 Barcelona Wine Bar | 4180 Black Rock Tpke, Fairfield, CT ⭐️⭐️⭐️⭐️⭐️
Thursday: A Travel Day, Panera in the Middle, Madison Social at the End
Thursday was the real shift in the week — graduation travel down to Tallahassee.
We flew out of Westchester, but instead of flying into Tallahassee we flew into Jacksonville, because the flights into Tallahassee were genuinely more expensive than flying to Italy. Sometimes that’s just the math you have to live with. By the time we landed, picked up the rental car, and got on the road, lunch was non-negotiable.
We pulled off the highway at Panera Bread, and I’ll admit — I hadn’t been in years. The menu is completely revamped from what I remembered. So many more options, sandwiches, bowls, the works. I went with the Toasted Italiano, and it was honestly really good. Solid bread, decent meats, good flavor, and exactly the right kind of road-food meal — quick, predictable, and not regrettable. A pleasant surprise after a long-haul travel morning.
We rolled into Tallahassee around 3 p.m., which was the perfect time to walk the FSU campus, swing through the bookstore for the last bit of senior swag, and start working up an appetite. By dinner, we landed at Madison Social in College Town, the Bobby-Bowden-adjacent district that anchors the FSU food and bar scene.
Madison Social has the location everybody wants — overlooking Doak Campbell Stadium, with garage doors that open up to a huge patio. The energy is great, especially during a graduation weekend when the entire town is humming. The food itself was typical bar fare. Burgers, dips, salads, the usual. It was fine — perfectly fine — but nothing that I’d write home about. The atmosphere absolutely earned its keep, though, and on a graduation eve, that counted for a lot.
After dinner we drove over to Thomasville, GA, our home base for the weekend, about thirty miles north of Tallahassee.
📍 Madison Social | 705 S Woodward Ave, Tallahassee, FL ⭐️⭐️⭐️
Friday: Discovering Thomasville
Friday started slowly at the AirBnB, which was exactly what we needed.
A quick bite, a slow coffee, and then a walk through downtown Thomasville — and let me say, this was one of those small American towns I had no expectations for that turned out to be completely charming. The downtown is full of brick streets, old storefronts, and the kind of curated independent shops that you don’t find in many places anymore.
Kevin’s Fine Outdoor Gear & Apparel (locally just called “Kevin’s”) was a real highlight — the classic Thomasville landmark that’s been outfitting hunters and Southern style lovers for over 40 years. Big, beautiful store, gun room in the back, home goods, gifts, the works. We picked up a few things and kept moving. The antique stores along the same stretch were also fantastic, the kind where you could lose an hour without realizing it.
For lunch, we ducked into The Dog and Pony, a proper British-style pub right on Broad Street. My wife and I both got the Philly Toastie, which was outstanding — pressed, crusty, melty, properly seasoned, the kind of sandwich that makes you wish you’d gone earlier in the day so you could have had two. My son grabbed the burger, and that landed too. The space itself has that warm pub atmosphere that does a lot of the work for the food. Wood, low light, friendly bartenders, the whole thing.
📍 The Dog and Pony | 213 S Broad St, Thomasville, GA ⭐️⭐️⭐️⭐️⭐️
By evening, we were back in Tallahassee for graduation-weekend hangouts. Apps and drinks at Bowden’s in College Town — the Bobby Bowden tribute restaurant with a beautiful big patio and one of the better-looking spaces in the area. Then over to Township, a beer hall–style spot that has somehow turned out to be the place where graduation dads can be found embarrassing themselves on the dance floor. I will say no more.
Saturday: Graduation Day and a Steakhouse Surprise at St. James
Saturday was the day. Slow morning at the AirBnB. Cooked breakfast in the kitchen — eggs, bacon, the usual — because we had to be in our seats at the FSU graduation by 1 p.m. and a real lunch was off the table.
After the ceremony, the plan was clear: get back to Thomasville, snack lightly, and save room for dinner. And dinner, as it turned out, was the meal of the trip.
St. James in Thomasville is a wood-fired hearth-and-grill restaurant that the locals had been quietly telling us about all weekend. Within five minutes of sitting down, I understood why. The space, the energy, the staff, the menu — this place was on a different level.
We started with a dozen oysters, a mix of Wellfleet, Rappahannock, and Apalachicola, and they were exactly what you want from a serious oyster program. Briny, sweet, clean, every variety hitting a slightly different note. Cold drinks, fresh shells, ice melting just slowly enough — it was the right way to start.
Then came the Brussels sprouts appetizer, which was a serious dish in its own right. Crispy, charred at the edges, balanced with something tangy and a little sweet — one of those vegetable plates that you keep going back to until you realize you’ve eaten most of it yourself.
I went with the 8oz filet, and it was outstanding. Properly seasoned, beautifully cooked, the kind of cut where everything around the steak — the sides, the sauce, the plating — knows enough to step back and let the meat do the talking. Everyone at our table loved their meals, and the drinks program kept up the entire night.
Dessert was a small showdown between the key lime pie and the bread pudding, and honestly, both won. The key lime had that perfect tart-sweet balance that you only get from a place that takes the dish seriously, and the bread pudding was warm, rich, and exactly right for a long celebratory evening.
This was the kind of restaurant you remember. Not just the food, but the way the whole evening felt — graduation behind us, the family relaxed around the table, no rush, no pressure, the dishes coming out one after another like the night was being orchestrated.
📍 St. James | 1145 W Jackson St, Thomasville, GA ⭐️⭐️⭐️⭐️⭐️
Sunday: Empire Bagel, A Long Drive, and Birria in Savannah
Sunday morning started with one final Thomasville stop — Empire Bagel & Delicatessen in the heart of downtown.
Empire is a real find. Family-owned, run by a New York native who knows what a proper bagel should look and feel like, and you can tell the second you walk in. The space is small and inviting, the bagels are warm and chewy in the way they should be, and the breakfast sandwiches looked excellent up and down the line. A great cup of coffee, a proper bagel, and a calm Sunday morning was the perfect goodbye to a town we’d genuinely fallen for.
📍 Empire Bagel & Delicatessen | 221 W Jackson St, Thomasville, GA ⭐️⭐️⭐️⭐️⭐️
After breakfast, the family split up. My wife and the rest of the kids took the rental car back to Jacksonville to fly home. I stayed back at FSU with my youngest to help her pack up the car for the long drive north. By the time we finally pulled out of Tallahassee, it was 4 p.m. — way later than planned, and the drive home suddenly looked enormous.
We charted a stop in Savannah, GA to break up the trip. Rolled in around 8 p.m., starving, not in the mood for a full sit-down dinner. We landed at La Parrilla Mexican Restaurant on Abercorn, and it turned out to be exactly the right call. Fast, generous, and surprisingly good for a regional chain.
I went with the Birria Bowl and my daughter went with the Birria Tacos. Both were excellent — rich, deeply spiced beef, the broth doing all the heavy lifting in that classic birria way. The tacos came with a proper consommé for dipping, and the bowl was hearty enough to feel like a real meal even after a day of driving. And maybe most importantly: the food came out fast. Like, almost shockingly fast. After a 4-hour drive with another travel day ahead, that mattered as much as the flavor did.
📍 La Parrilla Mexican Restaurant | 7804 Abercorn St, Savannah, GA ⭐️⭐️⭐️⭐️
Closing Reflection
This was not a normal week. It was a graduation week, a road-trip week, a watch-your-youngest-daughter-cross-the-stage week. The food was secondary to the moment.
But maybe that’s why a few of these meals stood out the way they did. The Philly Toastie at The Dog and Pony in a sleepy Georgia downtown. The dozen oysters and 8oz filet at St. James after my daughter graduated. The warm bagel at Empire on the way out of town. The fast, satisfying birria in Savannah at the end of a hard day on the road. None of those meals would have hit the way they did if the week around them hadn’t been built on something bigger.
Some weeks the table holds the food.
This week, the food held the family.