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Our City Guide is an insider’s guide for marketing leaders — real recommendations, local perspective, and the places that make this city worth experiencing beyond the conference.
Five years ago, I would have told you I’d never move to Tampa.
I genuinely didn’t understand the appeal. I thought it was sleepy. Retiree-heavy. Golf courses and early dinners. If you asked me where the energy was in Florida, Tampa wouldn’t have been my answer.
Fast forward to today, and I catch myself asking a very different question: when can I move to Tampa?
I live in Sarasota, but as President & GM of the Tampa Bay Sun FC, our headquarters and training facility are in Ybor City. I’m here constantly. What started as a commute slowly turned into something else. Tampa became a second home — not in theory, but in rhythm. It’s where I work. It’s where I build. It’s where I’ve watched something shift.
And the best way to understand Tampa is to start where I spend most of my time: Ybor City.
Ybor is five minutes from downtown, but it feels like you’ve crossed into another country. Brick streets. Historic cigar factories. Roosters wandering around like they own the place — and technically, they’re protected, so they kind of do. The first time you see one casually strolling past you while you’re eating tacos, you’ll do a double take. Then you’ll realize this is just normal here.
Ybor was built by Cuban, Italian, German, and Spanish immigrants who turned Tampa into the cigar capital of the world in the early 1900s. Everyone thinks of Ybor as the place to go party — and it absolutely can be — but what makes it special is that you can still see those four immigrant cultures layered into the architecture, the food, and the family names that have been here since the beginning of the 20th century. It’s not history behind glass. It’s living.
Cubans, Coffee, and Pickleball Spots in Ybor City
If you landed early for Digital Summit and texted me, “Where do I grab coffee before my first meeting?” I’d send you to Café Quiquiriqui inside Hotel Haya.
The name alone makes me smile. Quiquiriqui is Spanish for “cock-a-doodle-doo.” My dad used to say it when I was little. When I first walked in and saw the name, I wondered if anyone else knew what it meant. Most people don’t. But the coffee is incredible. True Cuban coffee. Get a small café con leche — or if you want it sweeter, ask for a leche con café. The barista will know exactly what you mean. The space is lush and filled with plants, and you can tuck into a corner and work without feeling rushed.
Hotel Haya itself is worth lingering in. The bar scene is fantastic, and it captures what Ybor does well — historic and cultural, but fresh and alive.
Blind Tiger Café is another go-to, not just because the coffee is strong, but because they’re actively helping people with zero to three years of experience find jobs. That undercurrent of community investment shows up everywhere here.
If we stayed in Ybor for lunch, I’d make you try a Cuban sandwich — and then I’d explain the ongoing fight between Miami and Tampa about who invented it.
Miami will tell you they did. Tampa will argue otherwise. The difference? It’s the mayo. But honestly, the real secret is the bread. There’s a bread company here called La Segunda, and they deliver all over Tampa. If you’re eating a Cuban in Ybor, there’s a very good chance it’s on La Segunda bread, and you can taste the difference immediately.
I once had a friend order a Cuban sandwich in an Irish pub in Ybor and thought, who does that? He said, “It’s an Irish pub in Ybor City. Trust me.” He was right.
There’s also a women-owned pickleball warehouse, Tampa Pickleball Crew, in Ybor that’s incredible — huge indoor space, great energy. It’s about 10–15 minutes from the Hilton. If you wanted to do something unconventional during the conference, that would be a fun way to gather people.
And here’s the beauty of it: Ybor is five minutes from downtown, and the yellow trolley runs between them constantly. You can start your morning with a café con leche in Ybor and be downtown for a meeting in under ten minutes without ever needing a car.
Hop back toward downtown and you’ll feel the shift immediately. The brick streets give way to glass towers, a growing collection of speakeasies, and a Riverwalk that has quietly become the spine of the city.
If you need a quieter coffee option near the Hilton, Little Tina is low-key and perfect for getting work done. Downtown has added new cocktail spots and hidden bars over the last few years, and there’s noticeably more energy than there used to be.
Where to Raise a Glass
If you want a drink with a view, go to The Beacon on top of the JW Marriott. Yes, it’s technically a franchise. But you get a 360-degree view of downtown, the bay, even all the way to the airport. The cocktails aren’t cheap, but the view makes up for it.
For something more my speed, I love CW’s Gin Joint. It has a prohibition-era vibe, and I’m obsessed with gin — especially anything floral. They do it right.
There’s also The Hotel Bar, which is literally just called The Hotel Bar, across from the Hilton. I’m fairly certain that’s where everyone ends up at the end of the night.
If you flew in a day early or have a free afternoon between sessions and you’re thinking, “I have a few hours — what should I actually do?” here’s my advice:
Places to Explore
Walk the Riverwalk.
It’s paved, pedestrian- and bike-friendly, and you can spend an hour or half a day on it. You’ll pass Armature Works, Ulele, and the University of Tampa — which has this stunning Byzantine-style architecture that looks like it was transplanted from somewhere in Eastern Europe. You’ll see it and think, where did that come from?
The Riverwalk is about a 10–15 minute walk from the Hilton, and it’s the easiest way to see Tampa without needing a car or a plan.
The Florida Aquarium is also right there and can be done in a couple of hours. The Tampa Zoo is worth it too. If you’re staying longer, there’s a park hopper option through Visit Tampa Bay that makes it easy to bundle experiences.
Best Bites in Town
At some point, you’re going to get hungry.
Wright’s Gourmet House is the sandwich spot locals swear by. When someone walks into a business meeting carrying Wright’s trays, the entire room lights up. They carve the deli meat fresh, layer it thin, and serve it on any bread you can think of — pumpernickel, marble rye, whatever you want. Add a slice of red velvet cheesecake and you’re done.
If you’re ready to venture a little further, Hyde Park is about 15–20 minutes from downtown — and it’s where Tampa flexes a more polished muscle.
For the big, impressive dinner, there’s only one answer: Bern’s Steakhouse. World-renowned. The wine cellar is one of the largest in the world. I’ve been at events in Germany where people have mentioned Bern’s by name. It’s the kind of restaurant locals book 30 to 90 days in advance for milestone birthdays. Reservations can be tough, but the bar is always a strategic option.
Hyde Park also has The Epicurean Hotel, Chill Bro’s ice cream with its local backstory, and Mac Dinton's Irish Pub where the college crowd gathers for sports. It’s a different vibe than Ybor — more boutique, more curated — but it shows another layer of the city.
For something equally iconic but more rooted in Tampa history, Columbia in Ybor is non-negotiable. Spanish-Cuban food, family-owned since 1903, and the 1905 Salad is a must. Yes, it’s garlicky. Yes, your breath will smell. You’ll survive.
Ulele, along the river, blends history with a broader American menu. It’s named after a Native American princess, and there’s a fable tied to the area. These aren’t once-a-year tourist stops. Locals go regularly.
But here’s what I really want you to understand about Tampa.
You can read about restaurants and bars anywhere. What you can’t Google is how a place actually feels.
The biggest misconception is that Tampa is slow and sleepy. It’s not. It’s relationship-based.
You don’t have one or two dominant players controlling the scene. Instead, you have a fabric of leaders across industries who know each other and show up for each other. As someone building a professional women’s sports franchise here, I can tell you — a city either shows up for growth or it doesn’t. Tampa shows up.
Two weekends ago, I was at the Cuban Club for their annual charity bocce ball event. All the big corporate partners in town were there. That’s how business happens here. Outdoors. In community. Over pickleball, over bocce, over conversation.
Nobody honks here. I’m serious. If someone honks, they’re not from here. I had someone honk at me in Sarasota the other morning and thought, what are you doing? We’re all taking our time.
Tampa is getting big-city infrastructure — more brands, more access, more visibility — but it still feels small enough to be human. You get the big-city wants without the big-city negatives.
Our beaches aren’t right outside downtown. Clearwater is about an hour away. But honestly, between the Riverwalk, Ybor, the food, and the culture, you won’t feel like you’re missing anything.
If I’m playing hooky from work, I’m renting an E-boat. Electric boats that anyone can operate. No license required. A few weeks ago, I was out there with friends — charcuterie boards, music, cruising at sunset. You can dock at Rick’s on the River, grab a drink, and head back out. It’s affordable, it’s easy, and it feels very Tampa.
March here is gorgeous. Warm, sunny, not unbearably hot. Locals will be in sweaters if it dips to 60. Hurricane season comes later, and when it does, we throw hurricane parties and bunker down together. Tampa Strong.
What I want people to know is this: Tampa is a place where you can live, work, eat, and play all within a tight radius. Whether you’re young, raising a family, or building something ambitious, there’s space for you here.
Five years ago, I said I’d never move here.
Now, every time I drive back to Sarasota after a long day in Ybor, I find myself calculating how much longer that commute will last.