The Sea, Cigars and Gator Tails: Here’s How to Tour Tampa, Florida, in Just 3 Days

It’s often overlooked in favor of flashier Florida cities. But Tampa is a don’t-miss destination, filled with culture, history and outdoor adventure. There aren’t many places where it’s possible to lounge along a pristine shoreline, explore a vibrant downtown and let out a few screams aboard some of the country’s top roller coasters.

The variety of things to do is endless, and that’s not even counting the thriving dining scene. Suffice it to say, from day to night the Big Guava has you covered.

As always, check for travel restrictions and closures before planning your trip

Friday: Take in Downtown’s Museums

Your first day is centered around the city’s famous (and beautiful) 2.6-mile pedestrian trail along the Hillsborough River, known as Riverwalk.

To start, grab a bite at the stylish Oxford Exchange (where the smoked salmon everything bagel is amazing), then make your way to the Tampa Bay History Center. This interactive museum provides a fascinating and informative look at pirates, Tampa’s history, Florida’s Indigenous people and more.

After history class, try out a water bike — for the uninitiated, imagine a surfboard topped with a stationary bike, powered by pedals (and you, obviously). You can rent one from Tampa Water Bike Co. to cruise down the waterfront and see downtown Tampa from a new angle.

All that activity calls for a bite to eat. Stop at one of the sandwich or hamburger spots on your way to the Tampa Museum of Art (we recommend Samaria Café, which serves Mediterranean fare, including Greek salads, gyros and more).

If it’s a family trip, cool off at Water Works Park along the Hillsborough River, a large playground that has a “splash pad,” featuring a big bucket-like container of water that periodically tips its contents onto the children below.

Then pop down the street for dinner at an upscale food court called Heights Public Market. The variety of vendors — from photo-worthy cookies at Bake’n Babes to rice and noodle dishes at Bento Asian Kitchen — ensures nobody leaves hungry.

Try to hit up Heights on the early side to leave time for sunset water sports on the river as your final activity.

Urban Kai leads regular evening waterway tours on stand-up paddleboards. Or simply rent a boat at Goko Kayaks and enjoy a self-guided paddle

Before heading back to the hotel, check out the popular hockey-themed Hattricks Tavern or the sprawling waterside bar and hangout spot called the Sail Plaza, where every hour is “yappy hour” — meaning dogs are not only welcome, they drink (water) and eat (biscuits) for free.

Saturday: Explore the Ybor City Neighborhood

A trip to Cigar City is incomplete without visiting the historic area that gives Tampa its nickname. Grab a bite at the hotel before finding a trolley that will take you to Ybor City, where the streets are lined with cigar shops, authentic Cuban bakeries and historical sites.

Learn about the area’s early days at the Ybor City Museum State Park. For lunch, try the so-called “best Cuban sandwich in the city” at the family-run La Segunda Bakery, where they’ve been baking their own bread (and pastries) since 1915.

After filling up, it’s time to stake out the stogies. Stroll down Seventh Avenue and pop into galleries, boutiques, cafés and cigar shops. Watch as the experts hand-roll their wares at spots like Tabanero Cigars and J.C. Newman Cigar Company. (This is also a great chance to pick up souvenirs.)

Just before dinner, pay a visit to José Martí Park, which the country of Cuba actually owns — this pocket park has been Cuban territory since 1956.

From there, stop for dinner at Columbia restaurant, a family-run business since 1905, serving Cuban and Spanish dishes. Don’t miss the filet mignon “chacho” or paella a la valenciana.

The night doesn’t end there: This neighborhood is filled with bars that play music, pour daiquiris (a drink that originated in Havana) and — especially at the Tampa Bay Brewing Co. — serve up local craft beers.

Sunday: Head to the Amusement Parks

Before jumping into what will be a busy day, stop for breakfast at Mamas Kitchen, where the “bennies” are bountiful — eggs-Benedict-style dishes, that is.

Then it’s off to an amusement park (or parks, if you’re ambitious enough to take on two). Adventure Island is your coolest choice for a hot afternoon because it features waterslides with twists, turns and delightfully frightening drops. For a mellower way to get wet, relax in the park’s half-mile lazy river.

You can also rent an all-day cabana as your home base, complete with lounge chairs and a minifridge.

Dry off before checking out one last Tampa must-see: Skipper’s Smokehouse, just 5 miles from Adventure Island. Kick back with the nightly live entertainment and indulge in some extremely “Florida” fare. (Yes, that means fried gator tail is on the menu.) Is there a better way to end a whirlwind weekend in Tampa?