We’ll start the day with a little exercise. Don’t worry. You’ll have a cocktail in hand by noon.
Park on S. Delaware Ave in front of any of the restored American Craftsman bungalows or Georgian-inspired brick homes. As long as you don’t see a ‘five-minute parking’ sign, your car will be fine.
Walk south toward the water. At the end of the street we’ll do a little celebrity home spotting. You see the palatial brick house on your left? That’s Jill Kelley’s, the woman who exposed the emails that prompted the resignation of former CIA director David Petraeus. Imagine the paparazzi lined up in the alley behind the home.
Dart across the four lanes of traffic to the water. Shade your eyes and scan the coastline to your left. See the sprawling cream-colored home with the rounded walkways? That’s the home of baseball great Derek Jeter. Well, one of his homes.
Now we’re on Bayshore Boulevard, which at 4.5 miles holds the title of World’s Longest Continuous Sidewalk. This is where Tampanians come to run, bike, walk, and bird watch. If it’s before 9:30 the sidewalk will be crowded with Tampa’s AM athletes. Any later and you may have the street all to yourself. Do your thing. Run. Walk. Weave up and down Willow and Newport Avenues, two of the prettiest streets in Tampa.
After, hop back in the car and take Bayshore to Datz. Their Meatloaf Paradise, a dish stuffed with mac and cheese, was recently featured on the Travel Channel. But we’re here for breakfast. Try the Brie Bardot or Breakfast BLT. The Datz A Mary includes a garnish of bacon.
Stuffed? No judging if you head back to your hotel for a nap.
Chances are you’re staying downtown, home of the greatest concentration of hotels and a quick cab ride from all the stops on our tour.
Walk to Curtis Hixon Park. Those minarets across the Hillsborough River mark the University of Tampa, formerly the Tampa Bay Hotel. Rooms that housed Teddy Roosevelt and his Rough Riders, the Prince of Wales, and the Queen of England are now classrooms, labs, and lecture halls. Babe Ruth reportedly signed his first baseball contract in the hotel’s dining room.
Standing at the water, look to your left. That bridge marks Kennedy Blvd. You probably drove it to get to this morning’s activities. The street got its name because JFK’s motorcade traveled it just four days before his assassination.
At the park you can borrow a hula hoop or a frisbee from the rental stand, or just sit on a bench and take in the water and the downtown crowd as they lunch. Return to the park often during your trip. You may catch a concert, yoga class, or outdoor movie night. Curtis Hixon is also a great spot to watch the bridges over the Hillsborough River light up with colored LEDs as part of the city’s nightly Agua Luces art display.
Next, pop into the Tampa Museum of Art, home to a small collection of antiquities, rotating modern art exhibitions and, most importantly, a frigid AC. Grab a sandwich, gelato, or Lemonciata-based cocktail at the museum’s Sono Cafe.
After lunch, take Polk Street to the Tampa Theater, built in 1926, and pose for a picture in front of its vertical sign. Pop into the Duckweed Urban Market, where they pack caviar, quail eggs, and Himalayan pink salt — along with staples like milk, bread, and mac and cheese — into less than 600 square feet of space.
Grab a cab. We’re going to Ybor City.
Chances are you missed the Gasparilla Pirate Festival, a winter parade in which hundreds of boats invade the harbor and Tampa’s elite, dressed as pirates, demand the mayor overturn the keys to the city. You can get a taste of Tampa’s pirate culture when the cab drops you off at Gaspar’s Grotto. Say “argh” and shell out $2 for a shot of bottom-shelf whiskey and a PBR. Eat some chicken wings and a cuban sandwich on the outside patio.
A little loosened up, walk down 7th Ave, my favorite strip in Tampa. Peek into the tattoo shops and cigar-rolling booths. By now the motorcycles and thumping Chevys on 24-inch rims that cruise the streets are probably out for the night.
After rummaging through the vintage jewelry and clothes for sale at La France and Revolve Clothing Exchange, pop into Hamburger Marys, one of a recent surge of businesses geared toward the LGBT community and friends that have earned this area the affectionate nickname GaYBOR. If you missed the drag show, have a beer at the bar.
Head inside King Corona Cigars and pick a cigar from one of the dozens in the store’s convenience-store-beer-case-size humidor. The staff can help if you don’t know what you’re doing. Try to grab an outside table for people watching over more beers.
Sober up with a slice from the window at New York Pizza across the street. Walk back toward where we started on 7th Ave to take it all in. By now the night is in full swing and Ybor is at its finest. If you can handle it, grab one more beer at Boneyard, a dive bar full of Christmas lights and non-functional toilets that serve as tables.
Hail a cab home. Chug some water. Pop an aspirin and sleep well.
Best Travel Credit Cards
Top offers from our partners
Chase Sapphire Preferred® Card
80,000 bonus points
The Platinum Card®
75,000 bonus points
American Express® Gold Card
60,000 bonus points