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Boating along the Hillsborough River by Downtown Tampa (Photography by Gabriel Burgos)

Iconic Ways to Explore Tampa Bay

Immerse Yourself in the Best of the Region

by Leah Ching
December 30, 2022
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Tampa Bay is profoundly shaped by the people that make up its diverse, multi-cultural population. This New Year, we’re celebrating the people that call Tampa Bay home – longtime locals and newcomers alike. We cherish the rich legacy of our past, alongside today’s residents who are molding and shaping the region for future generations. Tampa welcomes an average of 149 residents daily, with the region ranking No. 3 on a list of U.S. areas people want to move to.

People continue to flock here in record numbers with no signs of slowing. Tampa Bay ranked as the hottest housing market in 2022. Half of the people searching for homes in the region are from outside of the area, with 15% of all Florida home purchases happening in Tampa.

The following guide will help locals and visitors explore the heart of Tampa Bay. We’ve rounded up the most iconic ways to experience the local culture and immerse yourself in the best of the region.

Get on the Water
Perhaps Tampa Bay’s most coveted asset is its abundant waterfront. For those ready to embrace the nautical lifestyle, Ultimate Marine and other local boat dealers make it easy to dive into boat ownership with a large inventory of the best, most sought-after vessels. Not ready to purchase? Consider fun day rentals such as eBoats or tiki tours. If you’d rather kick back and have someone else do the work, crewed charters with Sunburst Yacht Charters are pure luxury, no hassle. Skippers who enjoy switching up their seafaring vessel will love a boat club membership with Carefree Boat Club, Freedom Boat Club or Sovereign Boat Club. Of course, the Pirate Water Taxi is a perfect day adventure with 15-plus stops in Downtown Tampa.

Bayshore Boulevard

Stroll the Scenery
Boasting more days of sunshine than the U.S. average, Tampa Bay is ideal for filling a calendar with outdoor activities and experiences. The beaches are a must, but you’ll also want to explore picturesque neighborhoods by bicycle or on foot. Bayshore Boulevard, the world’s longest sidewalk, offers unmatched views of the bay and access to South Tampa’s best neighborhoods, including the mansion lined streets of Bayshore Beautiful and pedestrian friendly Hyde Park. A little further north, the Tampa Riverwalk is a bustling community line of 2.6 miles, offering access to Tampa’s downtown and waterfront. In St. Petersburg, the award-winning St. Pete Pier is teeming with activity.

Gasparilla Pirate Festival

Discover the Pirate’s Life
Pirate costumes are not just for Halloween here. Tampanians have been hosting an annual Gasparilla pirate fest, the city’s most popular annual event, nearly every year since 1904. At the center of the festivities is a parade of pirates and a boat parade led by the Jose Gasparilla II. The city gets “turned over to a parade of pirates” and swashbuckling festivities carry late into the evening. Mardi-gras style meets coastal flair for this historic, dynamic festival, complete with a children’s parade.

Tampa Bay Buccaneers boat parade

Cheer on the Teams
Not only is the region home to major league champion-winning teams, but also premier stadiums and arenas for prime game viewing. Fire the cannons every time the Tampa Bay Buccaneers score at Raymond James Stadium. Feel the electricity during a Lightning game at Amalie Arena in the heart of Tampa’s downtown. The Tampa Bay Rays play at Tropicana Field in Downtown St. Petersburg, as do the Tampa Bay Rowdies just a few blocks over at the Al Lang Stadium near the waterfront. The local Tampa Bay team spirit is thriving and the city cores are buzzing on game day, so if you weren’t a fan, it won’t be long until you’re sporting team colors. Just like lots of other New Yorkers, the New York Yankees head to Tampa Bay for Spring. Along with five other MLB teams, they complete their spring training in Tampa Bay. And, who can forget college ball? Annually, on New Year’s Day, the ReliaQuest Bowl is held at Raymond James featuring teams from the SEC and Big Ten. Sporting fans, rejoice.

Corona Cigar Co.

Light up a Stogie
It won’t take long to realize that cigars are woven into Tampa Bay’s cultural fabric. Once the cigar-making capital of the world, one only needs to walk the cobblestone streets of historic Ybor to see how Latin cultures from Tampa’s cigar-making heyday have become a part of the city’s heartbeat. Dubbed Cigar City, the nickname stuck and so did the broader region’s affinity for lighting up a stogie. Cigar lounges line the streets of Ybor. Other swanky smoking spots are found in Hyde Park (Casa de Montecristo), Westshore Business District (Corona Cigar Co.), and along Beach Drive in St. Petersburg (Cigar Paradise). Stewards of cigar culture, Tampa is also home to Grand Cathedral Cigars, named Cigar Journal’s Best Lounge in the World and J.C. Newman Cigar Company, the last traditional cigar factory still operating in the United States.

A Cuban sandwich from La Segunda Bakery

Eat Like a Local
For newcomers, stumbling onto Tampa Bay’s vibrant culinary scene is often a serendipitous surprise. Not as well known as its larger regional counterparts, Tampa Bay is replete with famous, historically significant dining institutions, award-winning eateries and critically acclaimed chefs. A prime coastal location and temperate weather mean excellent seafood and waterfront dining year-round. You won’t go long without hearing about grouper sandwiches, which is thought to have originated in this region. Although Miami likes to brag, Tampa takes the prize for its Cuban — dubbed the city’s signature sandwich by the Tampa City Council. Try one at La Segunda, makers of cuban bread since 1915.  Much of the region’s cuisine is shaped by its early immigrant populations so you’ll want to devour the renowned Latin cuisine at the Columbia Restaurant (like their famous Spanish Bean Soup) and award-winning steak at Bern’s Steak House. Newer restaurants (including 19 Michelin-recognized ones) add flair to the scene, which continues to grow.

BarrieHaus Beer Co.

Do a Brewery Crawl
Tampa Bay has emerged as an unexpected leader in the craft beer scene, earning the nickname the “Gulp” Coast. Home to 50-plus craft breweries, there are thriving hubs in Ybor City, Seminole Heights and Downtown St. Petersburg where drinkers can do a brewery crawl on foot. Breweries range from large nationally-awarded brands (Cigar City Brewing) to underground haunts with cult followings (Angry Chair Brewing) and boast epic live music shows (3 Daughters Brewing) and foodie-worthy grub (Tampa Bay Brewing Co.). Whatever your taste, checking breweries off your list is an excellent way to explore.

Gasparilla Music Festival

See a Live Show
An arts and culture haven, Tampa Bay attracts some of the world’s most acclaimed music, comedy and theater performers to venues like Amalie Arena and The Duke Center for the Arts. Outdoor venues like the MidFlorida Credit Union Amphitheatre and Jannus Live allow music lovers to indulge in music and mild weather year-round. From Blues and EDM to indie and reggae – music festivals abound. Branch out and check out a play at Stageworks, performances by The Florida Orchestra, stand-up comedy at the Tampa Improv or an independent film at the Tampa Theatre.

The James Museum of Western & Wildlife Art

Take in the Art Scene
There’s a reason Tampa Bay has become a hub for artists and creators: Creativity flourishes across the region. You’ll find world-renowned museums like the Tampa Museum of Art, The James Museum of Western & Wildlife Art, The Dalí and The Museum of Fine Arts. A plethora of independent galleries such as The Chihuly Collection and Michael Murphy Gallery reflect the region’s deep reverence for art. Works of the world’s most pre-eminent artists can be viewed along with historic artifacts and contemporary collections. Smaller galleries celebrate the talent of local creators. Immerse yourself and be inspired.

Tampa Bay History Center

Learn the History
From the rich contributions of the Seminole tribes to the enormous impacts of Tampa’s Cuban immigrants, there are countless places to start exploring Tampa Bay’s history and luckily, so many individuals and organizations are dedicated to preserving and paying homage to the area’s past. Visit the Tampa Bay History Center, the Ybor History Museum and Henry B. Plant Museum in Tampa. In St. Petersburg, take a trip to The Florida Holocaust Museum, St. Petersburg Museum of History and St. Petersburg Shuffleboard Club (the oldest and largest shuffleboard club in the world). But, one doesn’t have to go to a museum to learn history. Walk the streets of historic Ybor, Hyde Park, Kenwood and Rosier Park. Historical markers and public art are all around the region to enlighten those curious enough to look.

Learn more about the Impact of the Tampa Riverwalk.

Tags: best of Tampa Bayboating Tampa BaybreweriesBuccaneerscigar cityexplore Tampa Baygasparillahistory Tampa BayTampa Bay guidetampa food
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