Begin in Ybor City, a historic one-square-mile neighborhood northeast of downtown Tampa built around the Cuban cigar industry. Founded by Spanish cigar manufacturer Vicente Martinez-Ybor, the area is registered as a National Historic Landmark. Eat freshly baked Cuban bread, cafe con leche and pastries at La Segunda Bakery. Opened in 1915, the family-run Cuban bakery bakes 18,000 loaves of bread daily. Next, view exhibits on Ybor’s founding and the cigar industry and tour a restored casita at Ybor City Museum.
Then, walk to 7th Avenue, which is flanked by century-old red brick buildings housing cigar shops, boutiques, and restaurants. Don’t be surprised to see chickens crossing the road – they are descendants of the fowl of the neighborhood’s earliest residents. Enjoy lunch at Columbia Restaurant, Florida’s oldest restaurant. Signature dishes include the 1905 salad, named for the restaurant’s inaugural year and the Ybor City-invented Cuban sandwich (Spanish ham, Cuban mojo-marinated pork, Genoa salami, Swiss cheese, pickles and mustard on butter-brushed and pressed Cuban bread).
Walk off lunch with a stroll along the 2.4-mile Tampa Riverwalk and board a water taxi to sail Tampa Bay and possibly spot dolphins. Cross over the Hillsborough River for retail therapy at Hyde Park Village, an outdoor arcade with boutiques and cafes, before concluding the day with dinner at Bern’s Steakhouse. Since 1956, Bern’s Steakhouse has been aging steaks, serving vegetables grown on their farm and perfectly pairing wines from their collection of half a million bottles. Visit the steakhouse’s dessert room and indulge in King Midas, a carrot cake with spiced pecans and almonds served with macadamia nut ice cream and hot fudge.
With near-constant sunshine and warm water, every day is beach day. Eat flaky croissants and French toast at La Croisette on St. Pete Beach, a barrier island filled with white sugar sand beaches like Fort De Soto Park, which spans five islands. Explore Fort De Soto Park’s Spanish American-era fort, nature trails, museum and fishing pier. Take a 20-minute ferry ride across the emerald green waters to Egmont Key to snorkel in near solitude.
Get a taste of old Florida along the four-mile-long Pass-a-Grille Beach and browse the shops along Eighth Avenue Historic District before taking a 10-minute ferry ride to Shell Key, an uninhabited barrier island. Finally, watch the sunset from the third floor of The Hurricane in Pass-a-Grille Beach. Opened in 1977, the casual seafood restaurant is the perfect place to sip sundowners and dine on the signature grouper sandwich and Mom’s 1945 Crab Cake.
Begin the day with warm cinnamon rolls with cream cheese glaze and fresh strawberries at Oxford Exchange, a bistro, Champagne bar, bookstore and gift shop in a century-old space in downtown Tampa. Enjoy brunch in the sun-drenched glass-ceiling conservatory before browsing the bookstore and shop stocked with globetrotting treasures. Then, go to St. Pete to see the Chihuly Collection by contemporary artist and pioneer of glass art, Dale Chihuly. Admission includes glass blowing demonstrations at the Morean Glass Studio and Hot Shop across the street. The Chihuly Collection is on Central Avenue, home to trendy retail shops and restaurants, ranging from a candle pouring boutique to a baked potato cafe to a funky teashop. Stop for lunch at New American restaurant and wine bar Brick & Mortar, which has a seasonally changing menu.
After lunch, walk east to The Dalí Museum, home of the largest collection of Salvador Dalí’s work outside of Spain. After admiring the Surrealist art, get lost in the museum’s lush labyrinth, the Avant-garden. Dine at Rooster and The Till, an eclectic 72-seat restaurant in Tampa’s Seminole Heights. Helmed by Chef Ferrell Alvarez, the award-winning restaurant serves an ever-changing degustation menu. Conclude at CW’s Gin Joint in downtown Tampa, which boasts stylish cocktails, retro ambiance and – frequently – live jazz.