The Gulf Coast's got a packed weekend ahead, and I'm not even sure where to start. Spring training kicks off with three games across two stadiums. TINA roars through Van Wezel. The Florida Man Games are actually happening (yes, really). And if you want to squeeze in a Greek festival, a circus under a big top, AND a Tina Turner musical, nobody's stopping you.
This is one of those weekends where the Sarasota-St. Pete corridor just goes off. I've been covering events here for years, and the density of things happening February 20-22 is almost ridiculous. Spring training alone would make this a destination weekend, but then you add in two major seafood festivals, a 42-year-old Greek tradition, Winter Pride celebrations, and the actual Florida Man Games? It's a lot.
I've curated this list to help you figure out what's actually worth your time. Not everything that says "festival" delivers festival energy, and not every spring training game has the same vibe. I've tried to give you the real talk on what to expect.
All dates and details were verified through official sources as of February 2026. You can find more events in the Sarasota-Tampa Bay area on AllEvents.
Events are ordered by a mix of timeliness and "you can't do this any other weekend" factor. I've included the greater Tampa Bay area since everything from Safety Harbor to Bradenton to Plant City is within reasonable driving distance. Each listing tells you what it is, why you might care, and the practical stuff you need to know.
What: MLB Spring Training kicks off with the New York Yankees visiting the Baltimore Orioles on Friday, then the Pittsburgh Pirates on Saturday. This is opening weekend for the Grapefruit League, and Ed Smith Stadium is ground zero for Sarasota baseball.
Why go: Opening weekend spring training has an energy that mid-March games just don't match. Everyone's optimistic, the weather is perfect, and you're watching future World Series rosters figure themselves out. The Yankees bring their traveling fanbase, which makes for an electric atmosphere even in a 7,500-seat stadium.
Who it's for: Baseball fans who want the spring training experience without the late-February price gouging. Also perfect for families since kids can actually see the field and maybe snag an autograph during warmups.
When: Friday, Feb 20 at 1:05 PM (Yankees at Orioles); Saturday, Feb 21 at 1:05 PM (Pirates at Orioles)
Need to know: Ed Smith Stadium, 2700 12th St, Sarasota. Tickets typically run $20-45 depending on seating. Get there early for parking since the lots fill up. The stadium has great sight lines from almost every seat, and the beer selection has improved dramatically in recent years.
What: The Tampa Bay Rays head to Bradenton to take on the Pittsburgh Pirates in one of the first intra-Florida spring training matchups of the season. LECOM Park is a classic Grapefruit League venue with that old-school charm.
Why go: This is technically a road game for the Rays, but it's only about 45 minutes from their Port Charlotte facility, so expect a decent Tampa Bay contingent. The Pirates are rebuilding (again), but their young talent is worth watching. Plus LECOM Park just feels like what spring training should be, small, intimate, with players accessible before and after games.
Who it's for: Anyone who wants to see baseball without the big stadium feel. Great for casual fans who want to actually relax rather than navigate a massive complex.
When: Sunday, Feb 22 at 1:05 PM
Need to know: LECOM Park, 1611 9th St W, Bradenton. About 20 minutes from downtown Sarasota. Parking is included with your ticket purchase. Food options inside are decent but not spectacular, so consider hitting Bradenton's downtown restaurants before or after.
What: The touring production of the Tony-nominated jukebox musical about Tina Turner's life and career makes its Sarasota stop. This is the full Broadway touring production with "Proud Mary," "What's Love Got to Do with It," "River Deep, Mountain High," and basically every hit you'd want to hear.
Why go: Look, jukebox musicals can be hit or miss, but TINA works because Tina Turner's story is genuinely wild. The domestic abuse, the comeback, the legs. The performer playing Tina has to absolutely belt for two hours straight, and reportedly this touring cast delivers. Van Wezel's acoustics are underrated, and seeing this show with a Florida crowd that probably saw Tina live in the '80s adds energy.
Who it's for: Anyone who's ever sung "Proud Mary" in the car. Theater fans who don't mind their musicals heavy on the hits. Absolutely not for people who get annoyed by audience members singing along (because they will).
When: Friday, Feb 20 at 8 PM; Saturday, Feb 21 at 2 PM and 7:30 PM; Sunday, Feb 22 at 1 PM and 6:30 PM
Need to know: Van Wezel Performing Arts Hall, 777 N Tamiami Trail, Sarasota. Tickets from $70-200+ depending on the performance. The Saturday matinee tends to be less crowded. Van Wezel's parking lot fills up, so arrive 30+ minutes early or consider the overflow lot.
What: One of the longest-running Greek festivals in Florida returns for its 42nd year. Three days of souvlaki, gyros, pastitsio, spanakopita, loukoumades, and baklava. Live Greek music and dancing. Church tours. The works.
Why go: The food alone is worth the trip. This isn't some sad festival gyro situation, this is a Greek Orthodox church community that's been perfecting these recipes for four decades. The pastry table is genuinely overwhelming in the best way. The folk dancing performances happen throughout the day, and there's something pure about watching yiayias teach kids the steps.
Who it's for: Food lovers. Families looking for a cultural experience that doesn't require much planning. Anyone who's ever said "I could go for some Greek food" and meant it.
When: Friday, Feb 20 from 11 AM - 9 PM; Saturday, Feb 21 from 11 AM - 9 PM; Sunday, Feb 22 from 11 AM - 6 PM
Need to know: St. Barbara Greek Orthodox Church, 7671 N Lockwood Ridge Rd, Sarasota. $5 admission, free for kids under 12. Cash is king for food booths, though some accept cards. The parking lot gets chaotic, but there's overflow parking with shuttles. Go hungry, leave with a box of pastries.
What: A three-day festival at Vinoy Park combining fresh seafood, live music, arts and crafts vendors, and waterfront views of downtown St. Pete. This is the sixth annual, and it's grown into a proper destination event.
Why go: Vinoy Park might be the most beautiful festival location in the Tampa Bay area. You've got the marina, the pink Don CeSar visible across the water, downtown's skyline as your backdrop. The seafood focus means you're getting Gulf shrimp, stone crab claws when available, grouper sandwiches, and fried everything. Sunday headliner Damon Fowler is a Tampa Bay blues legend worth catching.
Who it's for: People who want to combine eating seafood with actually being by the water. Live music fans who prefer sitting on grass over standing in a sweaty club. Dog owners (it's dog-friendly).
When: Friday, Feb 20 from 4 PM - 10 PM; Saturday, Feb 21 from 11 AM - 10 PM; Sunday, Feb 22 from 11 AM - 6 PM
Need to know: Vinoy Park, 701 Bayshore Dr NE, St. Petersburg. General admission around $10 at the gate. Street parking is limited so use the paid lots along Beach Drive. Sunday afternoon is actually the sweet spot: smaller crowds, Damon Fowler on stage, cheaper parking. Tickets available on AllEvents.
What: Sarasota's hometown circus returns under the big top at Nathan Benderson Park. This year's show features performers with over 18 world records collectively, including AGT finalists, Guinness record holders, and acts you genuinely won't see anywhere else.
Why go: Sarasota was literally the winter home of Ringling Bros. for decades, so circus here isn't just entertainment, it's heritage. The Circus Arts Conservatory puts together a professional show that rivals anything touring nationally, but with that intimate big-top atmosphere where you're close enough to see the performers' expressions. The Olate Dogs (AGT Season 7 winners) are on this year's bill. It's genuinely impressive.
Who it's for: Families, obviously, but honestly anyone who appreciates physical artistry. Circus arts have evolved way beyond what most people picture. This is contemporary circus, not just elephants and clowns.
When: Friday, Feb 20 at 2 PM and 7 PM; Saturday, Feb 21 at 2 PM and 6 PM; Sunday, Feb 22 at 1 PM and 5 PM
Need to know: Big Top at Nathan Benderson Park, 5851 Nathan Benderson Circle, Sarasota. Tickets $40-100, with an $18 order fee that includes parking. The tent is climate-controlled. Show runs about 2 hours with intermission. Concessions available inside.
What: Yes, this is a real thing. Competitive events inspired by actual Florida Man headlines, held at Cleetus McFarland's Freedom Factory. Past events have included the "Evading Arrest Obstacle Course," "Beer Belly" competitions, "Catalytic Converter Theft" (simulated), and "Weaponized Pool Noodle Jousting."
Why go: Honestly? Because where else are you going to see this. The Florida Man Games has become a legitimate viral phenomenon, and experiencing it in person is genuinely absurd in the best way. The Freedom Factory crowd brings energy, the events are more athletic than you'd expect, and you'll have stories to tell. Is it lowbrow? Absolutely. Is it also weirdly impressive? Also yes.
Who it's for: People with a sense of humor about Florida. Anyone who's ever forwarded a Florida Man headline. Groups of friends looking for something completely different. Not ideal for small kids (the humor skews adult).
When: Saturday, Feb 21, starting at 9 AM
Need to know: Freedom Factory, 21050 E State Road 64, Parrish (about 30 min from downtown Sarasota). This event sells out or gets chaotic, so check their website for ticket availability. Bring sunscreen, it's an outdoor venue. Food trucks on site.
What: David Foster, the 17-time Grammy-winning producer behind hits for Whitney Houston, Celine Dion, and Chicago, performs alongside his wife Katharine McPhee (American Idol, Broadway's Waitress) in an intimate evening of music and storytelling.
Why go: David Foster has written or produced some of the biggest songs of the last 40 years, and his live shows are essentially a masterclass in pop music history. He'll sit at the piano, tell stories about working with Whitney or Barbra, then play the songs. Katharine McPhee has serious pipes and adds Broadway energy. The Mahaffey is an excellent venue for this, great acoustics and a proper theater feel.
Who it's for: Adult contemporary music fans. Anyone who grew up on '80s and '90s power ballads. Couples looking for an elegant night out.
When: Friday, Feb 20 at 8 PM
Need to know: Mahaffey Theater at Duke Energy Center, 400 1st St SE, St. Petersburg. Tickets from $65-150+. The theater's right on the waterfront, so grab dinner at one of the surrounding restaurants beforehand. Parking in the downtown garages.
What: Safety Harbor's annual waterfront festival featuring fine art and craft vendors, fresh seafood from local restaurants, and live music all weekend. The 2026 headliners are Beach Bumz Band (Jimmy Buffett tribute) and other local acts.
Why go: Safety Harbor is one of those Florida towns that still feels like Old Florida, and this festival captures that vibe perfectly. It's FREE, which is increasingly rare for quality festivals. The art is juried so you're getting actual artists, not just mass-produced stuff. And the seafood comes from established local restaurants, not random festival vendors.
Who it's for: Art collectors and browsers alike. Parrotheads (the Buffett tribute band is legitimately good). Families looking for a free, low-key waterfront afternoon.
When: Saturday, Feb 21 from 11 AM - 7 PM; Sunday, Feb 22 from 12 PM - 6 PM
Need to know: Safety Harbor Waterfront Park, 110 Veterans Memorial Ln, Safety Harbor (about 25 min from St. Pete). FREE admission. Parking can get tight so arrive early Saturday or go Sunday. The weather in February is usually perfect for this.
What: The operatic pop quartet Il Divo brings their candlelight tour to Mahaffey Theater. Two decades of emotional ballads, classical crossover, and that distinctive multinational sound (Spanish, French, Swiss, American) performed in an intimate setting.
Why go: Il Divo has sold 30+ million albums for a reason. Their "By Candlelight" tour strips things down with warm lighting and acoustic arrangements, which works beautifully for their repertoire. This is the kind of show where you might actually tear up, and that's fine. Mahaffey's acoustics let you hear every harmony.
Who it's for: Il Divo fans (they know who they are). People who appreciate classical-pop crossover. Anyone who wants a Sunday afternoon of beautiful music without having to think too hard.
When: Sunday, Feb 22 at 3 PM
Need to know: Mahaffey Theater, 400 1st St SE, St. Petersburg. Tickets from $60-175+. Sunday afternoon timing means you could combine this with brunch and still make it home at a reasonable hour.
What: St. Pete's Winter Pride celebration includes the glamorous Pelican Ball (Monte Carlo themed, open bar, live entertainment) on Friday and the signature Drag Race street event on Sunday. The Pelican Ball is headlined by Angeria Paris VanMichaels from RuPaul's Drag Race.
Why go: St. Pete has one of the most vibrant LGBTQ+ communities in the Southeast, and Winter Pride is their flagship celebration. The Pelican Ball is genuinely elegant, not your typical bar night, think formal attire and an event that's been refined over years. The Sunday Drag Race on Central Avenue is free and brings incredible energy to the Grand Central District.
Who it's for: LGBTQ+ community members and allies. Anyone who enjoys drag performance. People looking for St. Pete's party scene at its most festive.
When: Pelican Ball: Friday, Feb 20 at 8 PM at The Floridian; Drag Race: Sunday, Feb 22 on Central Avenue (time TBD)
Need to know: Pelican Ball tickets required and tend to sell out. Drag Race is free and open to all. The Grand Central District has plenty of bars and restaurants to make a full day of it. Check Winter Pride Saint Pete's social media for exact Drag Race timing.
What: The first-ever live film-to-concert experience of Dirty Dancing. The complete film plays on a massive screen while a live band and singers perform the soundtrack, including "(I've Had) The Time of My Life," "Hungry Eyes," and "She's Like the Wind."
Why go: If you've seen Dirty Dancing 47 times (no judgment), seeing it with a live orchestra changes things. The emotional moments hit harder when there's a real singer belting the soundtrack. Ruth Eckerd Hall is one of the best venues in Florida for this kind of hybrid experience, excellent sight lines and sound.
Who it's for: Anyone who can quote the entire movie. People who love '80s nostalgia done right. Couples who want a date night that's more interesting than just going to dinner.
When: Saturday, Feb 21 at 8 PM
Need to know: Ruth Eckerd Hall, 1111 McMullen Booth Rd, Clearwater. Tickets from $45-85. The show runs about 2 hours (the full film length). Parking is free and plentiful.
What: A vintage marketplace dedicated to Florida memorabilia, ephemera, kitsch, and collectibles. Think mid-century postcards, orange crate labels, old roadside attraction souvenirs, vintage maps, and all the Florida nostalgia you didn't know you needed.
Why go: There's nothing else like this. If you have any interest in Florida history, design, or just kitschy Americana, this is a goldmine. Over 25 vendors specialize specifically in Florida-related vintage items. It's the kind of place where you'll find a 1950s brochure for a long-demolished tourist trap and absolutely have to buy it.
Who it's for: Collectors. Design enthusiasts. History buffs. Anyone who gets excited about retro Florida aesthetics.
When: Friday, Feb 20 from 2 PM - 6 PM; Saturday, Feb 21 from 9 AM - 3 PM
Need to know: Sarasota Fairgrounds Potter Building, 3000 Ringling Blvd, Sarasota. $10 admission (good for both days). Bring cash since not all vendors take cards. Saturday morning has the best selection before things get picked over.
What: Keel Farms' annual celebration of strawberry season featuring a strawberry shortcake eating contest, live music, food vendors, farm activities, and their award-winning wines and beers. It's a working farm with a winery and brewery on-site.
Why go: Plant City is strawberry country, and Keel Farms does this festival right. The shortcake eating contest is legitimately entertaining. You can sample their strawberry wine (don't knock it until you try it), explore the farm, and spend a few hours in the Florida countryside without going too far from civilization.
Who it's for: Families with kids. Wine and craft beer enthusiasts. Anyone who wants to do something outdoors that isn't a beach.
When: Saturday, Feb 21 and Sunday, Feb 22 from 10 AM - 3 PM
Need to know: Keel Farms, 5202 W Thonotosassa Rd, Plant City (about 45 min from Sarasota, 30 min from Tampa). FREE admission, $10 parking. They have food trucks but also their own kitchen. Dog-friendly.
What: FREE outdoor movie screening of Pixar's SOUL at the St. Pete Pier. Bring a blanket or chair, grab food from the pier's restaurants, and watch the sunset before the movie starts.
Why go: It's free, it's on the pier, and SOUL is legitimately one of Pixar's best films. The St. Pete Pier location is beautiful at sunset, and there's something special about watching a movie outdoors with the water behind you. Plus the pier has excellent food options, so you can make it a whole evening.
Who it's for: Families. Budget-conscious date nights. Anyone who wants to experience the pier after dark.
When: Friday, Feb 20 at 6:30 PM
Need to know: St. Pete Pier, 600 2nd Ave NE, St. Petersburg. FREE. Bring your own blanket or chair. Parking in the pier garage or nearby lots. Get there early for a good spot and to watch the sunset.
What: Joe Dombrowski, better known as "Mr. D" from viral classroom prank videos that have racked up hundreds of millions of views, brings his standup act to Tampa. He's a former teacher turned comedian whose material centers on education, kids, and the absurdity of modern life.
Why go: If you've ever seen the "spelling test prank" videos, you know this guy is genuinely funny. His standup expands on that energy without just being "the guy from the videos." Side Splitters is an intimate room where comedy actually works, not a huge theater where you're watching on screens.
Who it's for: Teachers (they need this). Parents. Anyone who appreciates observational comedy about everyday life.
When: Friday, Feb 20 and Saturday, Feb 21 with shows at 6:30 PM and 8:45 PM
Need to know: Side Splitters Comedy Club, 12938 N Dale Mabry Hwy, Tampa. Tickets $25-35. Two-drink minimum. The late shows tend to be looser.
Garden Music Series at Selby Gardens (Feb 22, 1-3 PM): Danielle Mohr performs in one of America's most beautiful botanical gardens. $25 with garden admission. Perfect Sunday afternoon vibes.
Mezzo Market (Feb 21, 11 AM - 4 PM): 165+ small business vendors on Baum Avenue in downtown St. Pete. Free to browse, dangerous for your wallet.
Saturday Morning Market at Al Lang Stadium (Feb 21, 9 AM - 2 PM): St. Pete's signature weekly market with food, produce, and crafts. Year-round institution.
Rays vs. Braves at Charlotte Sports Park (Feb 21, 1:05 PM): If you want to see the Rays at home during opening weekend, this is it. Port Charlotte is about an hour south.
Bradenton Public Market (Feb 21, 9 AM - 2 PM): Old Main Street comes alive with vendors, food, and live music. Good pre-Pirates game activity.
What's the weather like in Sarasota in late February? Usually perfect. Expect highs around 75-80°F, lows in the mid-60s. Rain is possible but unlikely. Bring sunscreen for outdoor events.
Can I do spring training and a festival in the same day? Absolutely. Games start at 1:05 PM and run about 2.5-3 hours. You could catch the Greek Festival, Seafood Festival, or Art & Seafood afterwards.
What's the best area to stay? Downtown Sarasota puts you close to Van Wezel, Ed Smith Stadium, and the Greek Festival. Downtown St. Pete puts you close to the Seafood Festival, Mahaffey shows, and the pier. Both are about 45 minutes apart.
Is the Florida Man Games actually good? It's chaotic, sweaty, and ridiculous. If that sounds like fun, yes. If you need your events polished and organized, maybe skip it.
Which spring training stadium is better, Ed Smith or LECOM? Ed Smith has better amenities and food. LECOM has more character and feels more old-school. Both are good, just different vibes.
This weekend has something for basically every type of person. Grab tickets to what speaks to you, and I'll see you somewhere between the big top and the gyro line.
