The Beat writer Jack Kerouac, who lived and died in St. Petersburg in the 1960s, said that the city was ideal for the “newlywed and the nearly dead.” Kerouac wouldn’t recognize the city now. It’s a booming and contradictory place that’s cool but unpretentious, with a thriving gay scene and an abundance of Midwestern exiles who don’t do winter. Visitors who reckon that Florida has little to offer beyond beaches, strip malls and subdivisions are surprised by the city’s distinctive architecture and cultural offerings. Two devastating hurricanes 13 days apart last fall wreaked havoc on the region, displacing thousands. But the hurricanes also revealed that despite all the growth, the “Sunshine City” is still a friendly burg where neighbors take care of each other. Those in search of a cultural oasis with pristine beaches, warm weather and plenty of character will find that St. Pete is back open for business and as appealing as ever.

On Sept. 1, 1910, the publisher of The Independent, a St. Pete newspaper, “challenged the world” with a “reckless offer”: free copies of the newspaper on every day the sun didn’t shine. The promotion lasted 76 years, until the paper went out of business, and it was free on just 296 days, or about four times a year. Visit the informative St. Petersburg Museum of History ($15; $6 on Sundays) on the lively St. Pete Pier for stories like these that illustrate how the weather, baseball and an alleged fountain of youth helped turn St. Pete into a resort town. The museum has the world’s largest collection of autographed baseballs plus exhibits on the women who helped build St. Pete and the highwaymen — 26 African American artists who were unable to exhibit their work in Florida galleries because of discrimination so instead sold their work along U.S. 1 in the 1960s and 70s to earn a living.

Walk a few blocks to the Birchwood Inn’s rooftop bar, Birchwood Canopy, on fashionable Beach Drive, for spectacular views of Tampa Bay and happy hour (4 to 7 p.m.) specials that include $4 beers, $7 glasses of wine and $8 cocktails. Then take a ride share west along Central Avenue, the city’s main drag, to the lively Grand Central District for a memorable dinner at Pulpo Kitchen + Lounge, which opened in December but is already one of the city’s best restaurants. Sit outside near where the Latin band and D.J.s perform, and feast on delicious small plates like pulpo gallega with papas bravas (Galician octopus with smashed potatoes in a creamy aioli sauce, $22), sweet plantains with garlic herb chimichurri ($7) and calamari stuffed with squid ink rice ($12).

For an offbeat way to burn a few calories and have some fun, head over to the St. Petersburg Shuffleboard Club — the nation’s oldest and largest — for the club’s Friday night shuffle (7 to 10 p.m. $10). It’s an all-ages St. Pete tradition that’s a nod to the city’s past and a fun way to meet local members of the club, who will be happy to share tips.

Stay up late for a bar crawl along Central Avenue, which is loaded with options for all tastes. La La has private karaoke rooms, or settle into one of the plush, vintage couches at Lost and Found, which feels like crashing a 70s house party and has live music, a monthly pickleball tournament and a vintage market. If you’re traveling with a dog, or just happen to like dogs, check out the Dog Bar, St. Pete’s answer to the Westminster Dog Show, or on a hot night, Mutts & Martinis, which has a full-size pool with fountains for dogs to cut loose in.

Boating is an ingrained part of the culture in Tampa Bay; visitors can enjoy kayaking at Weedon Island Preserve.

Wake up early and head over to Cozy Uptown Eats for their excellent homemade scones ($5) and biscuits ($4), filling breakfast sandwiches on brioche buns, or their Gouda and white pepper grits with bacon, collard greens and a fried egg ($12), which sells out as often as the sun shines. Alternatively, drive west to Gulfport, a small, artsy city bordering St. Pete and Stella’s, a terrific breakfast option with plentiful outdoor seating that’s named after the owner’s late aunt, a nun from Manhattan’s Lower East Side. Favorites like the Mel’s breakfast burrito ($14.99) are, as advertised, a “hard habit to break.”

Arrive early at the Saturday Morning Market, where you’ll have a chance to buy souvenirs at stalls like Blue Twist & Co, which has cool art prints, or treats from vendors like Caribbean Quenched, which has refreshing fruit smoothies. Then take a bike tour catering to your interests. There are several to choose from, including one with St. Pete Biking, which takes visitors to see more than 40 murals painted by local and international artists ($59 or $79 for an e-bike). Josette Green, a local historian, leads Black history bike tours to untouristy, historically African American neighborhoods like Pepper Town, Methodist Town and the Deuces, while detailing ugly aspects of the city’s history, such as the Jim Crow era, when Black residents were effectively prohibited from venturing north of Central Avenue after dark.

12 p.m.Pick your sport: Baseball, tennis, pickleball — or shopping?

St. Pete was the venue for the first Major League Baseball spring training camp, in 1914, and the subsequent presence of Babe Ruth and other sluggers at hotels like the Don Cesar and the Vinoy boosted tourism. The city is still a great base for spring training (Feb. 21 to March 24), so try to take in a Yankees, Phillies or Blue Jays game, as they’re all within a half hour’s drive. Before you go, order a pair of lobster salad rolls (two for $10) online from Mazzaro’s, St. Pete’s deservedly popular Italian market, or a chicken tikka masala Bollywood bowl ($12.25) at Twisted Indian, a terrific fast casual Indian eatery on Central Avenue. If baseball’s not your thing, book a tennis or pickleball lesson at the Racquet Club of St. Petersburg and then enjoy lunch al fresco in the club’s delicious eatery, Root + Clay, which has superb chimichurri chicken sandwiches ($14). If shopping rather than sports suits your tastes, the Grand Central District has a host of shops. ARTpool, for example, has a huge selection of reasonably priced vintage clothing and records, and Tombolo Books is a small independent bookstore that’s particularly well stocked with L.G.B.T.Q. and progressive authors. Farther east along Central Avenue toward downtown, Florida CraftArt is a nonprofit gallery that sells original paintings, sculptures and crafts from more than 200 Florida artists at reasonable prices.

The Burg punches above its weight on the museum front, so pick one based on your interests. At the stunning Dalí Museum ($32) you’ll see every stage of Salvador Dalí’s life and work and will learn that he wasn’t always a surrealist. The Museum of Fine Arts ($22) is in a stunning building and has an impressively curated and diverse collection of art and artifacts from ancient to contemporary with something for everyone. The James Museum of Western & Wildlife Art ($23) is a must for those who like Native American art. If you’re traveling with children, let your kids indulge their curiosity and have fun playing at the Great Explorations Children’s Museum ($15 kids/$12 adults), which has interactive exhibits like a mini Publix grocery store, a doctor’s office and a fossil park.

Book a table outside at Pia’s Trattoria in Gulfport and you’ll feel like you’ve been invited to a wedding party somewhere in Italy’s Mezzogiorno. Their homemade ciabatta ($6 half loaf/$8 full) with olive oil is absolutely worth the carb splurge and their veal parmigiana ($35) with house-made linguini and lasagna with grass-fed, free-range Florida beef ($21) are divine. Take a neighborhood passegiata (stroll) and then cap the night with some quality craft beers at Webb’s City Cellar or 3 Daughters Brewing, which frequently has bands on weekends. On a hot night, enjoy the people watching at the block of bars immediately south of Williams Park downtown or do a beach bar crawl on St. Pete Beach starting at Coconut Charlies heading south to Salty’s Tiki Bar in the Tradewinds resort.

Jack Kerouac’s estate was valued at just $91 when he died in 1969 and he left it all to his mom, Gabrielle. Years of legal battles followed after her death in 1973, and in 2020, Ken Burchenal, a local Kerouac fan, purchased it and turned it into a nonprofit arts center and vacation rental. For a $100 donation, you can book a private tour of this three-bedroom midcentury home, which has been preserved exactly as the writer left it. On weekends, the house is often the venue for poetry and book readings, Saturday night concerts and a host of other events. And if you’d like to drink at one of Kerouac’s haunts, visit the Flamingo Sports Bar, which has a mural on the wall of Kerouac shooting pool and still looks a lot like it did back when he used to frequent it, often during daylight hours.

Visitors who reckon that Florida has little to offer beyond beaches, strip malls and subdivisions are surprised by the city’s distinctive architecture and cultural offerings.

If you’re an architecture buff, take a driving tour of some of St. Pete’s most distinctive neighborhoods before you head out to the beach. Old Northeast is full of classy prewar homes, which are rare in most of Florida; Snell Isle has mansions aplenty. Uptown and Kenwood have charming bungalows, and Pink Streets has gorgeous homes and brick streets painted pink, while leafy Driftwood is all arts-and-crafts-style homes hidden in a dense jungle. When you’re ready to eat, drive over to St. Pete Beach’s beloved breakfast spot, La Croisette. It closed during the pandemic but new owners from Corsica, who fell in love with the area while on holiday, have breathed new life into this neighborhood institution. The croissant French toast ($11.80) is exactly what it sounds like only better, and the omelets, breakfast sandwiches and pancakes are also first rate.

Boating is an ingrained part of the culture in Tampa Bay and no visit to the area would be complete without some sort of foray into the water. There are dozens of companies that run boat tours — a popular one is a clear kayak tour ($69 day/$74 night) of uninhabited Shell Key Preserve, a barrier island, with Get Up and Go Kayaking. The clear kayaks allow you to see into the water and the tour guides are knowledgeable. No kayaking experience is required and with any luck you’ll see dolphins and kayak through an enchanting mangrove tunnel, tides permitting. Alternatively, in St. Pete, you can rent kayaks and canoes at Weedon Island Preserve, which is also a pretty spot for a walk.

St. Pete Beach, named the #1 beach in America by Tripadvisor in 2021 but battered by hurricanes Helene and Milton in October, is back to its pristine glory, thanks in part to well-attended community beach cleanup events. Pass-a-Grille, a charming neighborhood at the south tip of St. Pete Beach where, centuries ago, fisherman stopped to grill their catches, has an atmospheric historic district and a few independent shops selling art and gifts along 8th Avenue that are worth exploring. But if you venture north, the beach is much broader than in Pass-a-Grille. Park around 22nd Avenue and walk north a bit until you find your own little piece of paradise.