25-ish Tampa Bay spots for breakups, hangovers and feeling alive
Our experts have a restaurant, park or fun spot for real life in Tampa Bay.
Tampa Bay Times reporters Gabrielle Calise and Helen Freund feel alive at Lassing Park in St. Petersburg.
Tampa Bay Times reporters Gabrielle Calise and Helen Freund feel alive at Lassing Park in St. Petersburg. [ DIRK SHADD | Times ]
Published May 25|Updated May 26

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.

Utah, a 5-year-old Australian cattle dog, holds a ball while visiting Shuffle in Tampa on Dec. 19, 2020.
Utah, a 5-year-old Australian cattle dog, holds a ball while visiting Shuffle in Tampa on Dec. 19, 2020. [ IVY CEBALLO | Times ]

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.

Spend your days with Hayes

Spend your days with Hayes

Subscribe to our free Stephinitely newsletter

Columnist Stephanie Hayes will share thoughts, feelings and funny business with you every Monday.

You’re all signed up!

Want more of our free, weekly newsletters in your inbox? Let’s get started.

Explore all your options

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.

The iconic sign lit up at St. Petersburg's historic Sunken Gardens.
The iconic sign lit up at St. Petersburg's historic Sunken Gardens. [ MARTHA ASENCIO-RHINE | Times ]

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.

Get One Day In Tampa Bay

Sign up for weekly emails with ideas for Tampa Bay day trips, secret spots, fun itineraries and more.

Get Stephanie’s newsletter

For weekly bonus content and a look inside columns by Stephanie Hayes, sign up for the free Stephinitely newsletter.