Tampa really did surprise me. My prior visits to Tampa, mostly during Florida road trips, left me with the impression that Tampa had seen better days.
Since Tampa recently received a downtown facelift with another $4 billion renovation project for the future, I wanted to explore the Big Guava (aka Cigar City) myself. Besides, several friends moved to the Tampa area and I wanted to find out why.
Goldilocks would love Tampa because it is not too big and not too small. I love a Tampa getaway from Northern Virginia in the winter because of the wonderful weather and vibrant foodie and craft cocktail scene. New craft beer joints open seemingly every week.
Tampa is an excellent carless vacation destination. Downtown Tampa is compact but there are plenty of public transportation options to take you where you want to go. To explore beyond downtown Tampa, ride share options (like Lyft and Uber) are readily available.
We were hosted guests of Visit Tampa Bay but this content is carefully crafted with the McCool Travel audience in mind.
5 Fun Ways to See Tampa Florida
1. Tampa Riverwalk and Tampa Downtown
The Tampa Riverwalk Trail begins near Tampa Bay History Center and ends in Water Works Park near Ulele restaurant (amazing oysters) and the fabulous food hall center Armature Works. Rent a bike through Coast Bike Share or stroll the entire 2.5 mile Riverwalk or portions of it. Snaking along the Hillsborough River, Riverwalk meanders under a couple of bridges and past a half dozen downtown parks, several other museums, fun hotels with al fresco dining/drinking areas, and the convention center. Hang out in one of the cool swings along the path. From Riverwalk, it was a short walk to meet a travel writer friend for a local craft beer at Holy Hog Barbecue.
See also our article about places to eat in Tampa: 10 Best Tampa Restaurants to Eat and Drink Local in Florida
2. On the Hillsborough River
While on the Riverwalk, you probably noticed University of Tampa students lounging in hammocks on the other side of the river. Get a closeup view of them from a rented water bike.
A more relaxing way to traverse the river is on the Pirate Water Taxi. It makes 15 stops in downtown Tampa, all the way north to Ricks on the River. Stop 14 is popular to visit Ulele and Heights Public Market—only open two weeks today—with some of the most creative and tasty food in Florida. We recommend a fresh Cuban dish from Hemingways or a lobster roll from Surf & Turf.
For a special thrill, rent a mini-powerboat from Riverwalk Boating. Available for as little as 30 minutes, this is a super fun way to see Tampa Florida. During potentially busy times, make a reservation though the website to make sure you do not miss the fun.
3. Ybor City
Dr. Wallace Reyes once held the Guinness Record for longest rolled cigar and is an Ybor City history expert. During a two hour walking tour of Ybor City, Wally entertained, educated, and surprised us. We saw cigars being hand rolled, learned why the brick streets are curved (fascinating), and visited Cuba. WHAT? Jose Marti Park, less than a quarter acre in the middle of Ybor City, belongs to the Cuban government (since 1956). The flora is native to Cuba and planted in soil transported from each province. So, I stepped on Cuban soil in Cuba although I never left Tampa. Pretty cool.
Dr. Reyes is one of a handful of people with access to it. To quench our thirst, we met some travel writer friends at Cigar City Cider & Mead, for yummy and potent fruit ciders and mead (honey based adult beverages). Travel between Ybor City and downtown Tampa on the TECO streetcar.
4. Bayshore Boulevard
For spectacular Hillsborough Bay and million dollar home views, Bayshore Boulevard is a super fun way to see Tampa. Officially called Bayshore Linear Park Trail – Bayshore Greenway, the “world’s longest sidewalk” begins across the river from the convention center and extends 4.5 miles along Bayshore Boulevard to (almost) Ballast Point Park.
Explore the Old Hyde Park neighborhood behind those elegant mansions—enjoy the majestic oak trees, cobblestones streets, and quirky artistic house exteriors and properties—the decor is especially quirky during Gasparilla Festival season.
Epicurean Hotel is a short 1/4 mile from Bayshore Boulevard and right across the street from the epic Bern’s Steak House (with over a half million bottles of wine. WOW!). After dinner at Bern’s or nearby Haven, visit Ciro’s Speakeasy—but make a reservation and receive the secret keyword, otherwise you cannot get in!
Epicurean Hotel guests can borrow one of their bikes or anyone can rent a Coast Bike Share bicycle. About a 2 mile ride from Epicurean is Oxford Exchange, a fabulous spot for breakfast or a business meeting.
>> Please see the McCool Travel article about staying at the Epicurean Hotel.
See our favorite Best Tampa Airbnbs or click below to book your own.
The Cross-Bay Ferry between downtown Tampa and St. Petersburg has only been operating for a few months. Board the ferry from near the Tampa convention center, then spend the day visiting the Dali Museum or catching a Rays baseball game. It is so great not to worry about traffic and parking, plus you get to experience the wonderful salt air mist and breezes. So fun!
See also these fun Florida travel articles:
- Fabulous Relaxed Luxury Resorts in Florida
- 19 Fun Day Trips From Orlando Florida
- Fun US Gulf Coast Bars, Breweries, and Beverage Spots
- US Gulf Coast Events: Fun Festivals in Southeast USA