It’s the dreaded question, an invitation for lazy shrugs and blank stares: “Where should we go?” If you’re lucky, you have that one friend who always has an answer, their brain a veritable catalog of cool eateries and hidden park benches.
If you’re really lucky, you have two such friends. Reader, you are really lucky. Culture and nostalgia reporter Gabrielle Calise and food and dining critic Helen Freund have teamed up to launch a sweeping new project a year in the making: One Day in Tampa Bay.
Their email newsletter comes every week, plotting out perfect days from downtown Tampa to Safety Harbor, the gulf beaches to Ybor City and more. Our sprawling region is overloaded with untapped day trips, and they’ve only just begun.
I was curious. Amid historic sites and boozy bruncheries, which spots might Helen and Gabrielle suggest for life’s more specific moments? You know, emotional highs and lows, awkward conversations, total interior meltdowns. I had to ask. They delivered.
A place to have an existential crisis
Gabrielle: I can’t decide between the line for New York New York Pizza in Ybor at 2 a.m. on a Sunday and the line for Wright’s Gourmet House when you’re scrambling to buy a last-minute birthday cake. Both elicit the same delirious feeling.
Helen: Trying to find parking in downtown St. Petersburg on a Saturday night. Trying to find parking near Water Street Tampa when the Tampa Bay Lightning are playing. Trying to find parking anywhere, really.
A place to be alone with your healing thoughts
Gabrielle: Lassing Park in St. Pete’s Old Southeast neighborhood. The perfect, quiet place to burrow in a hammock.
Helen: I love the Safety Harbor boardwalk for a quick and peaceful waterfront stroll. For a longer solo trek, an afternoon hike in Boyd Hill Nature Preserve in St. Petersburg.
A date spot to bring a love interest you’re on the fence about
Helen: Café Clementine at the Museum of Fine Arts, St. Petersburg. Can your date appreciate art? Beautifully constructed French pastries? Carbs? If not, it’s probably a deal breaker.
Gabrielle: Time for something fun and simple to release pressure: shuffleboard. The retiree pastime is cool now, and you can pick between Tampa Heights’ Shuffle, which serves food and drinks, or the St. Petersburg Shuffleboard Club, BYOB. If you end up falling in love, you can return to the game well into old age.
A place to break up with someone
Gabrielle: Craft Kafe in downtown St. Pete has outdoor seats spread far enough apart that you probably won’t be overheard. You can drop the news and flee.
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A hangover restaurant
Gabrielle: Pickford’s Counter in Seminole Heights, where you can quietly rot in a booth over a plate of loaded hash browns. Honorable mention goes to Trip’s Diner and their big, beautiful breakfast quesadilla.
Helen: The Salty Nun in St. Petersburg. Bloody Marys come with a giant strip of bacon, and the dill pickle grilled cheese is a surefire hangover cure. This place doubles as a solid neighborhood bar, so you can order a couple hair-of-the-dogs.
A hangout that feels beachy but is for people who hate the beach
Gabrielle: Crumps’ Landing in Homosassa. It’s a great little tiki bar that I love to stop by on the way to visit manatees or go scalloping in Crystal River. Their tropical salad comes with pineapples, mango and toasted coconut, which gives you that island vibe without actually having to get sand everywhere.
Helen: Bayou Bistro in Tarpon Springs. You’re right on the water, and the drinks are cheap and strong. It’s a locals’ hangout, so you won’t have to deal with beach tourists.
A place to propose that’s not fully cliche
Gabrielle: Sunken Gardens. There are plenty of little nooks to have a private conversation, and you can take ring photos by the flamingos after you get a “yes.” Bonus points: You can pack a little picnic and eat on the lawn.
A place to tell someone you gambled away the savings
Gabrielle: Mahuffer’s in Indian Shores, the diviest dive bar, complete with walls covered in dollar bills, very on-theme.
Helen: The Emerald Bar in St. Petersburg. If you know, you know.
A place to work with a laptop for four-hour stretches without getting side-eye
Helen: I love the breezy outdoor vibes at Cafe Vino Tinto in Safety Harbor. The cute, cozy patio and people-watching opportunities keep me entertained whenever I need a break from whatever I’m working on.
Gabrielle: Caffeine Roasters in Tampa. I like the location on Kennedy. You will pay $8 and up for a flavored latte with oat milk, but it’s worth it for access to their outlets and giant squishy couch.
A place to take your aunt from the Midwest
Gabrielle: Weeki Wachee Springs State Park. Between the mermaid performances in the underwater theater, tubing in the refreshing springs and the roaming peacocks, she will be dazzled.
Helen: Bern’s Steak House for the full, fine dining experience. Or a boozy tiki boat tour — totally opposite vibes, both quintessentially Tampa Bay.
A supposedly fun thing you’ll never do again
Gabrielle: Barhop on Tampa’s South Howard Avenue. I am too old for that!
Helen: I’ll never get on another scooter in heels.
A place to feel alive
Gabrielle: Sunset Beach on a weekday evening with a picnic blanket, a pollo asado sandwich from Bodega and a bottle of Mother Kombucha.
Helen: Cheap beers and oysters in the treehouse bar at Billy’s Stone Crab in Tierra Verde, right as the sun is setting. Bonus points if you sneak over to the secret beach across the street.
An insufferable secret that will impress people but also make them roll their eyes and talk about how you think you’re so much better than they are
Helen: Drinks at the Saint “Speakeasy” in St. Petersburg or the off-menu steak sandwich at Bern’s.
Gabrielle: You don’t have to stay at Dunedin’s Fenway Hotel to visit the rooftop bar. Get there well before dusk to secure your spot for their nightly “sunset celebration,” and order a flatbread to split. You might have to elbow past some blazers and sundresses to get there, but the view is worth it.
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