So often, we plan a big night out at just one restaurant — one destination-worthy meal.
I love an excuse for a destination dinner. But I often wish there was a place nearby to stop in for a predinner cocktail, and maybe a spot to swing by after for a nightcap or dessert, without having to get back in my car. As areas of Tampa Bay become more walkable (yes, we’re slowly getting there), neighborhood restaurants increasingly find themselves in good company, and that’s great news for diners.
Lately, I’ve been experimenting with the “date night shuffle” — hitting up a few spots along a walkable corridor, and sampling several dishes and drinks along the way. It makes the effort of the drive and potential parking fees feel worth it, and helps support a string of local businesses, rather than just one.
Beyond St. Petersburg’s busy Central Avenue (endlessly walkable!), the Tampa Bay area is home to several stretches where one can make a full night of it.
I’ve rounded up three of my favorite spots for a date night shuffle here, but we’ll plan on rolling more out in the coming months. Think of these as a sort of choose-your-own-adventure outing rather than a concrete directive. And if you’re planning on popping by any of these for Valentine’s Day, don’t forget to call ahead and make reservations.
What was once a semi-sleepy stretch along St. Petersburg’s Dr. Martin Luther King Jr. Street N has quickly become one of the ‘burg’s most bustling corridors. There’s a little bit of everything here, from family-friendly brewery hangs to cozy restaurants and bars with all the date-night feels.
A nice way to kick off an evening is at 86 Wine Bar, the latest spot to debut here, from owners Shane Schuch and Kendra Hardesty. Pop in for a glass of wine off their rotating list of low-intervention and biodynamic wines, and maybe a small snack from the short, always-evolving food menu. On any given week, that might include dishes like yellowfin tuna crudo with pickled yellow beets, grapefruit, white shoyu ponzu, avocado mousse and chili crisp, or a muffaletta flatbread.
If beer is more your thing, neighboring spot Golden Isles Brewing Co. is a great place to hang over a brew or two. I’m a fan of the If You Like Pina Coladas, a fruity New England-style IPA, but their Kolsch-style ale is also very good. If you’re looking to make a night of it here, the spot’s rotating cast of daily food trucks and pop-ups is always a solid bet.
Dinnertime presents a split in the road: Do you go more upscale and romantic, or more casual and laidback? If it’s the former you’re after, look no further than Calida, the charming (and petite) restaurant from Dayna Bennett and Ian Florence. A meal here is an exercise in intimacy, whether you’re cozied up at the tiny bar or seated in the small dining room. The menu changes frequently, but the squash and chorizo appetizer and the crispy-skinned duck breasts are both excellent choices.
If something more like pizza is calling your name, take a stroll to The Violet Stone, where extra well-done pies and killer Philly cheesesteaks have garnered the spot a big local fanbase. You can’t go wrong with a classic pizza topped with crispy, cupped and charred pepperoni. But an absolute must-order is the spot’s fried mozzarella sticks, which feature crunchy, breaded planks of gooey mozzarella and a side of the restaurant’s bright and juicy Bianca tomato sauce.
For dessert, head next door to Wildflower Ice Cream for the spot’s signature mix-and-match soft-serve creations, including house-favorite combos like The Lily (vanilla, peaches and graham crackers) and the Salty Sweet (chocolate, pretzels and caramel drizzle).
Liquid dessert more your thing? Might as well make it a full circle evening and head back over to 86 Wine Bar for a nightcap and — if available — a piece of their “Tira-Miso,” a play on the Italian classic made with a mascarpone miso cream and dark chocolate mousse.
86 Wine Bar: 2930 Dr. Martin Luther King Jr. St.N, Unit B, St. Petersburg. instagram.com/86winebar
Golden Isles Brewing Co.: 3000 Dr. Martin Luther King Jr. St. N, St. Petersburg. 727-502-9446. staygoldenstpete.com
Calida: 2909 Dr. Martin Luther King Jr. St. N, St. Petersburg. 727-202-0263. calidastpete.com
The Violet Stone: 2607 Dr. Martin Luther King Jr. St. N, St. Petersburg. 727-202-8940. thevioletstone.com
Wildflower Ice Cream: 2603 Dr. Martin Luther King Jr. St. N, St. Petersburg. 813-773-5490. wildflowericecreamshop.com
Do the Beach Boulevard shuffle down Gulfport’s busiest promenade. The late afternoon scene at Gulfport Brewery + Eatery is always a good spot to get started. Locals crowd the bar and cozy parlor during inclement weather, but if it’s nice out, the shaded back patio is where it’s at. The spot pours locally brewed beers on tap (bestsellers include the Unsteady Freddy IPA and Hippie Oasis hazy IPA) along with select wines and cider. There’s often live music here, and if you’re looking for a snack, the flatbreads and boiled peanuts are a great bet, and there are always rotating menu specials to check out.
Next door, the bright pink Wine House beckons. Grab a glass, or stay for a full bottle and a charcuterie spread. Wine and barbecue might seem like an odd combination, but it works surprisingly well here with platters of smoked brisket, chicken and pulled pork meeting their match with a fun and eclectic bottle program that boasts a solid selection of naturally fermented bubbles and light, juicy reds. There’s also a full lunch, brunch and dinner menu.
For a fast-casual dinner, cross the street and head to V-Roll, a new Vietnamese restaurant serving up classics like banh mi sandwiches, spring rolls and noodle bowls with a build-your-own model. The lemongrass pork and five-spice tofu are personal favorites, and signature sauces like the spicy V-bomb, citrus garlic and creamy peanut are all very good. Eat your meal on the restaurant’s patio or grab it to go (maybe with a bottle of wine from the Wine House) and hit up the Gulfport Beach Recreation Area, preferably right around sunset.
For a slightly more upscale vibe, Pia’s is a date-night must: It’s hard to find a place that turns up the romance as well as this restaurant. If you’re lucky enough to snag a coveted table inside the covered outdoor dining room, don’t pass it up. Otherwise, a table outside at neighboring Pia’s Veranda or a cozy seat at either bar is also lovely. The classics at Pia’s are always solid: the spaghetti di Bologna, the shrimp scampi and that killer lasagne. But it’s the daily specials that I usually gravitate toward, which might feature cloud-like carrot gnocchi one evening and a crispy duck confit the next.
Gulfport Brewery + Eatery: 3007 Beach Blvd. S., Gulfport. 727-954-4109. gulfport-brewing.com
The Wine House: 2913 Beach Blvd. S., Gulfport. 727-256-0228. pinkwinehouse.com
V-Roll: 2930 Beach Blvd. S., Gulfport. 720-474-0544. vrollrestaurant.com
Pia’s Trattoria: 3054 Beach Blvd. S., Gulfport. 727-327-2190.piastrattoria.com
Yes, the traffic getting here can be horrendous, and parking is a pain. But the posh downtown Tampa development’s central location and easy walkability make it a no-brainer when it comes to a date night shuffle. Plus, if you’re going to deal with the aforementioned traffic snarls and parking woes, why not hit up several spots and make it worth your time?
I like to kick off the evening with a dozen raw oysters and a martini over at The Pearl, Water Street’s lively anchor from restaurateur Cameron Mitchell. Though the briny bivalves are a highlight here, the gastropub-themed spot includes a full menu with several excellent predinner snacks, including deviled eggs and crispy-fried tater tots. If you’re looking for drinks with a view, both Azure, the rooftop restaurant at the Edition Hotel, and the Beacon at the JW Marriott Tampa Water Street are great options. Cocktails are pricey at both spots, but the downtown views — especially at sunset — are more than worth it.
For dinner, the Edition’s Michelin-starred Lilacoffers a splendid excuse for a splurge. The full tasting menu at the modern Mediterranean restaurant will run you $205, but the a la carte options offer more flexibility, and include dishes like a spice-crusted tuna with fennel and a cacio e pepe agnolotti with brown butter walnuts, scamorza cheese and truffle. The dining room here is quite small, so making a reservation beforehand is a must.
A more casual approach can be found at Ash, the Italian-inspired restaurant from the Proper House Group. Kick back inside the beautifully designed dining room or belly up to the dusty pink terrazzo-top bar for crusty focaccia served with boquerones, raw oysters served on the half-shell with candied kumquats and bay leaf oil, grilled prawn scampi with garlic scapes or the hearty (and very shareable) ribeye tagliata, served with confit tomatoes and crispy potatoes.
For dessert, you could indulge your sweet tooth with a pop-in to Chill Bros., the scoop shop with locally inspired flavors like Cafe con Leche and Tampa Banana. And if you’re still looking to turn it up, Boulongets really bumping right around 9 p.m. (and supposedly serves the best espresso martini in town). Down the street, Predalina’srecent makeover feels primed for a glamorous late-night hang.
For something a little more low-key, there’s Wine on Water, a tiny, charming wine bar and bottle shop from the team behind Tampa wine pioneers Cru Cellars. If you can’t make it into one of their weekly wine tastings (one of the best tasting deals in town), no sweat — the team here is always pouring a selection of interesting wines by the glass. There’s a short list of cocktails, too.
The Pearl: 823 Water St. C100, Tampa. 813-709-7776. thepearlrestaurant.com
Beacon: 510 Water St., Tampa. 813-314-6605. beacontampa.com
Azure and Lilac at the Edition: 500 Channelside Drive, Tampa. 813-771-8022. editionhotels.com/tampa/restaurants-and-bars
Ash: 420 S. Nebraska Ave., Tampa. 813-221-9191. ashtampa.com
Chill Bros.: 1061 Water St., Tampa. 813-999-0780. chillbros.com
Boulon: 1001 Water St., Tampa. 813-768-9988. boulontampa.com
Predalina: 1001 E. Cumberland Ave., Tampa. 813-344-3442. predalina.com
Wine on Water: 1057 Water St., Tampa. 813-921-0570. wineonwatertpa.com