Sarasota in late January is what Florida's supposed to be: warm enough to paddle a kayak at sunset, cool enough to make an evening at the orchestra feel cozy, and busy enough to remind you this stretch of Gulf Coast punches above its weight culturally. This weekend—Friday, January 30 through Sunday, February 1—delivers all of it.
You've got one of Rolling Stone's 50 Best Comics of All Time headlining at McCurdy's. You've got the Sarasota Orchestra going full Broadway with a program that includes Hamilton, Wicked, and Phantom. You've got Scottish Highland Games (complete with caber toss) at the fairgrounds. And for those willing to drive a bit, Tampa's biggest annual spectacle—Gasparilla Pirate Fest—storms Bayshore Boulevard on Saturday.
The mix is distinctly Sarasota: high culture and kitsch culture within a fifteen-minute drive, art festivals where you'll actually want to buy something, and enough outdoor activities to justify all those "we moved here for the weather" conversations. Pick your adventure.
How this list works: We've pulled from AllEvents, venue calendars, and our own research to build a list that's actually worth your time. Events span Sarasota County and nearby St. Pete/Tampa—because the best weekend in this region often involves a little driving. Prices and times verified at publication.
What it is: Multiple shows from one of the most successful touring comedians of the past two decades, headlining at Sarasota's intimate comedy club.
Why go: Russell Peters was recently named one of Rolling Stone's 50 Best Comics of All Time, and he's built that reputation through decades of sharp, observational material about culture, family, and the absurdities of modern life. His crowd work is legendary—half the fun is watching him riff with audience members in real time. McCurdy's is a perfect venue for this: close enough to feel the energy, small enough that every seat works.
Who it's for: Comedy fans, anyone who's seen Peters on Netflix and wondered if he's that good live (he is), couples looking for a memorable Friday or Saturday night.
Need to know: Friday, January 30 and Saturday, January 31 with shows at 6:30 PM and 8:50 PM both nights. McCurdy's Comedy Theatre, 1923 Ringling Blvd. Tickets around $37. Book ahead—he sells out.
What it is: The Sarasota Orchestra performs a full program celebrating history's greatest musicals at Van Wezel Performing Arts Hall.
Why go: This isn't a medley concert—it's a proper orchestral treatment of Broadway's biggest hits, from The Lion King and Hamilton to Jersey Boys, Phantom of the Opera, and Wicked. Jessica Vosk and Mauricio Martinez bring Broadway-caliber vocals, and conductor Evan Roider knows how to make a pops program feel like an event rather than background music. Van Wezel's bayside setting means you can grab dinner at one of the waterfront spots nearby and make an evening of it.
Who it's for: Musical theater fans, date night planners, anyone who's been meaning to experience the Sarasota Orchestra but hasn't pulled the trigger.
Need to know: Friday, January 30 at 7:30 PM; Saturday, January 31 at 2:30 PM and 7:30 PM. Van Wezel Performing Arts Hall, 777 N Tamiami Trail. Tickets at vanwezel.org or through AllEvents.
What it is: The 3rd annual Scottish Highland Games featuring traditional athletics, Celtic music, pipe bands, and Scottish clan gatherings at the Sarasota Fairgrounds.
Why go: Where else can you watch grown men throw telephone poles (caber toss), listen to massed pipe bands, and browse Scottish heritage booths all in one place? The Highland Games are a legitimately fun spectacle even if your only Scottish connection is a fondness for single malt. The heavy athletics competitions are surprisingly compelling—these are serious athletes doing things that look like they shouldn't be physically possible.
Who it's for: Families, history buffs, anyone with Scottish or Celtic heritage (or anyone who just wants to see strongmen throw weights), people who appreciate a good meat pie.
Need to know: Saturday, January 31, 9:00 AM – 5:00 PM (gates 8:30 AM). Sarasota Fairgrounds, Robarts Arena, 3000 Ringling Blvd. Children 12 and under free with adult. Kilts optional but encouraged.
What it is: A juried fine art and fine craft show ranked among America's Top 100, held outdoors at the Sarasota Art Museum.
Why go: Hot Works has been producing quality art shows for years, and this one delivers genuine variety—paintings, sculpture, ceramics, glass, jewelry, and more from artists across the country. Unlike some outdoor festivals where everything looks the same, you'll actually find pieces worth stopping for (and potentially bringing home). Free admission removes any barrier to browsing, and the Sarasota Art Museum location means you can duck inside to explore exhibitions between vendor strolls.
Who it's for: Art collectors, casual browsers, anyone looking for something more interesting than mall art for their walls.
Need to know: Saturday, January 31, 10:00 AM – 5:00 PM; Sunday, February 1, 10:00 AM – 4:00 PM. Sarasota Art Museum, 1001 S Tamiami Trail. Free admission.
What it is: Olympic-level show jumping under the lights at Fox Lea Farm, part of the Venice Equestrian Tour's winter series.
Why go: There's something genuinely thrilling about watching elite horses clear jumps at speed, especially at night when the arena lights turn everything theatrical. The $24,999 Grand Prix attracts serious competitors, and the atmosphere is surprisingly accessible—grab a drink at the pavilion, find a spot near the rail, and watch athletes (both human and equine) perform feats that never get old. It's one of those "only in Sarasota" experiences.
Who it's for: Horse enthusiasts, families looking for unique Friday entertainment, anyone curious about equestrian sports without wanting to commit to a full day competition.
Need to know: Friday, January 30, gates 5:00 PM, competition starts 7:00 PM. Fox Lea Farm, 800 N Auburn Rd, Venice. $10 admission, free parking. Runs every Friday through mid-March—if you miss this one, you've got options.
What it is: A theatrical Cher tribute concert at Van Wezel, featuring costume changes, hits across decades, and the full diva experience.
Why go: Done well, tribute shows can be genuinely fun—and this one commits. The production covers Cher's entire career, from Sonny & Cher days through "Believe" and beyond, with the costumes and staging you'd expect from someone impersonating a performer known for spectacle. It's unapologetically entertaining, and Van Wezel's acoustics make even nostalgic hits sound better than you remember.
Who it's for: Cher fans (obviously), '70s/'80s nostalgia seekers, anyone who wants to turn back time to a Sunday night with good music and elaborate outfits.
Need to know: Sunday, February 1 at 7:00 PM. Van Wezel Performing Arts Hall, 777 N Tamiami Trail. Tickets via vanwezel.org.
What it is: A paddling excursion timed to catch sunset transitioning into full moon over Sarasota Bay, led by guides from The Bay Park.
Why go: January 31 brings a full moon, and kayaking as the sun drops and moonlight takes over is one of those experiences that sounds Instagram-gimmicky but actually delivers. The guides know the water, the timing is calculated for maximum visual payoff, and there's something meditative about paddling into dusk that you don't get from most outdoor activities.
Who it's for: Outdoor enthusiasts, date night planners who want something beyond dinner, anyone chasing that "this is why I live in Florida" feeling.
Need to know: Saturday, January 31 at 5:00 PM. Launches from Kayak Launch at The Bay Park. Register via Eventbrite or thebaysarasota.org. Kayaks provided. Dress for getting slightly wet.
What it is: The 53rd annual invitational, juried indoor and outdoor fine art exhibition at Temple Beth-El in St. Petersburg.
Why go: More than five decades of curation means this festival knows what it's doing. The show features both established artists and emerging talent, and the indoor/outdoor split means weather doesn't ruin your afternoon. Purchase Award Preview Day (Saturday) lets serious collectors get first look before Sunday's general admission, and the setting at Temple Beth-El adds character you won't find at convention center shows.
Who it's for: Serious art collectors (Saturday), casual art lovers (Sunday), anyone making a Tampa Bay day trip who wants culture alongside whatever else they're doing.
Need to know: Saturday, January 31 (Purchase Award Preview Day, 1:00–4:00 PM) and Sunday, February 1 (general). Temple Beth-El, 400 Pasadena Ave S, St. Petersburg. About 45 minutes from downtown Sarasota—pair with other St. Pete activities.
What it is: Stand-up comedy from Tyrus—former WWE wrestler, current Fox News personality, and New York Times bestselling author—at Venice Community Center.
Why go: Tyrus's comedy is rooted in his unusual background: professional wrestling, political commentary, and a personal story that includes enough chaos to fuel multiple specials. His material is direct, observational, and doesn't pull punches regardless of whose feathers might get ruffled. Whether you know him from Fox or from his wrestling days, the live show is a different animal—more personal, more improvised, and definitely more profane.
Who it's for: Wrestling fans, Fox News viewers, anyone who appreciates politically incorrect humor delivered by someone who's lived an unconventional life.
Need to know: Saturday, January 31 with matinee (1:30 PM) and evening (7:30 PM) shows. Venice Community Center, 326 S Nokomis Ave, Venice. Tickets from $60 via Eventbrite.
What it is: Stand-up comedy under the stars from veteran comedian Rich Vos at the outdoor venue at Palmetto Marriott Resort & Spa.
Why go: Vos has been grinding the comedy circuit for decades—you've seen him on Gutfeld, Joe Rogan, Netflix, and basically every comedy platform that exists. His humor is classic road-comic stuff: unfiltered observations about marriage, aging, and everyday absurdity. The outdoor setting at The Yard adds atmosphere, and the resort location means you can make it a full evening with dinner and drinks.
Who it's for: Comedy fans who prefer raw club-style humor over polished specials, couples who want comedy plus resort vibes, anyone who appreciates a comedian who's earned his reputation the hard way.
Need to know: Saturday, January 31, 5:00 PM – 8:00 PM. The Yard at Palmetto Marriott Resort & Spa, 5315 Intracoastal Pointe Dr, Palmetto. About 15 minutes north of downtown Sarasota.
What it is: A theatrical tribute to Elton John's catalog at the Mahaffey Theater in St. Petersburg.
Why go: Elton John's Farewell Tour is done, so tribute shows are now the only way to experience those songs with a full band in a proper venue. This production doesn't cheap out—expect costumes, staging, and a performer who actually plays piano while delivering "Tiny Dancer," "Rocket Man," "Crocodile Rock," and the rest of the hits. Mahaffey Theater is a beautiful room, and Saturday night in St. Pete offers plenty of pre-show options.
Who it's for: Elton John fans mourning the end of his touring days, classic rock enthusiasts, anyone making a Saturday St. Pete trip.
Need to know: Saturday, January 31 at 7:30 PM. Duke Energy Center for the Arts – Mahaffey Theater, 400 1st St S, St. Petersburg. About 45 minutes from downtown Sarasota.
What it is: The legendary laser light show set to Pink Floyd's music, touring since 1987 and still filling theaters.
Why go: If you've never experienced a Pink Floyd laser show, it's genuinely worth seeing at least once—the combination of Dark Side of the Moon classics with elaborate laser programming hits different than watching a concert video at home. If you have seen it, you probably don't need convincing. Mahaffey Theater's sound system does justice to "Comfortably Numb" and "Money."
Who it's for: Pink Floyd devotees, psychedelic curious folks, anyone who wants a Sunday evening that feels like an event.
Need to know: Sunday, February 1 at 7:30 PM. Duke Energy Center for the Arts – Mahaffey Theater, 400 1st St S, St. Petersburg. About 45 minutes from downtown Sarasota.
What it is: Tampa's annual pirate invasion—one of the largest parades in the United States, featuring a flotilla of pirate ships, Bayshore Boulevard festivities, and approximately 300,000 attendees.
Why go: Gasparilla is spectacle on a scale Sarasota doesn't do. The Invasion begins at 11:30 AM as pirate ships sail into Tampa Bay, followed by the Parade of Pirates from 2:00–5:30 PM along Bayshore Boulevard. The crowd energy, the costumes, the beads, the sheer absurdity of a major American city surrendering to pirates—it's all part of the charm. If you've lived in the region and never done Gasparilla, this is your year.
Who it's for: Anyone who loves a big, weird regional tradition, families (parade is family-friendly), visitors who want to understand Tampa Bay culture.
Need to know: Saturday, January 31. Invasion 11:30 AM – 1:00 PM, Parade 2:00 PM – 5:30 PM. Bayshore Boulevard, Tampa. About an hour from downtown Sarasota. Expect traffic—leave early, or better yet, make a day of it and don't try to rush home.
What it is: The 17th annual Vietnamese Lunar New Year celebration in Lealman (near St. Petersburg), featuring traditional performances, food, and cultural activities.
Why go: Lunar New Year celebrations bring communities together, and this festival—hosted by the Vietnamese Catholic community—offers authentic cultural experiences: lion dances, traditional music, Vietnamese food vendors, and the kind of intergenerational celebration that makes you appreciate Florida's diversity. Year of the Snake festivities mean 2026-specific programming alongside traditional activities.
Who it's for: Anyone interested in Vietnamese culture, families looking for cultural education opportunities, food lovers wanting authentic Vietnamese cuisine.
Need to know: Friday, January 30 and Saturday, January 31. Lealman area (near St. Petersburg). Check Vietnamese Martyrs Parish Facebook page for specific times and location details.
What it is: A youth production of the popular Percy Jackson musical at The Players Studio, performed by middle school students.
Why go: If you've got Percy Jackson fans in your house, this is their weekend. The musical adaptation captures the humor and heart of Rick Riordan's books, and watching young performers tackle the material adds genuine energy. The Players Studio consistently delivers quality youth productions—these aren't cringe-worthy school plays but genuine theatrical experiences.
Who it's for: Families with Percy Jackson readers (ages 8+), grandparents looking for activities with grandkids, anyone who appreciates community theater.
Need to know: Thursday, January 29 through Sunday, February 1. The Players Studio, 1230 N Tamiami Trail. Evening and matinee performances available. Check theplayers.org for specific showtimes and tickets.
Kings of Leon in Tampa: Saturday, January 31 at 8:00 PM, Benchmark International Arena (formerly Amalie Arena). If you're doing Gasparilla and want to keep the Tampa day going, one of rock's most reliable live bands is playing that night.
Alexander Calder: The Nature of Movement: Marie Selby Botanical Gardens' current exhibition features the legendary sculptor's work amid the gardens—kinetic art in a setting that enhances everything. On view through spring 2026. Family Saturday programming on January 31.
Embracing Our Differences: Free outdoor art exhibition at Bayfront Park with 50 billboard-sized works promoting diversity. Open daily, free admission—perfect for a morning walk or pre-dinner stroll.
TJ Carney's 80s Night: Live band playing '80s hits, Saturday at TJ Carney's in Venice. If you want to sing along to "Don't Stop Believin'" with a crowd that remembers when it was new.
Q: What's the can't-miss event this weekend? A: For Sarasota proper, Russell Peters at McCurdy's delivers genuine star power in an intimate room. For spectacle, Gasparilla in Tampa is unlike anything else. For outdoor beauty, the Sunset + Full Moon Kayak Tour is perfectly timed.
Q: Best date night options? A: Sarasota Orchestra's Broadway program Friday or Saturday, followed by dinner on the waterfront. Rich Vos at Palmetto Marriott for comedy plus resort atmosphere. The Sunset Kayak Tour for adventurous couples.
Q: What about families? A: Highland Games work for all ages (kids love the heavy athletics), the Sarasota Fine Art Show is free and browsable, and The Lightning Thief musical is perfect for Percy Jackson fans. Kayak tour works for older kids comfortable on the water.
Q: How far is St. Pete/Tampa from Sarasota? A: St. Petersburg is about 45 minutes north. Tampa (for Gasparilla) is about an hour. Both are doable for a day trip, but if you're doing Gasparilla, plan for traffic and consider making a full day of it.
Sarasota, your weekend's mapped out. Whether you stay local or venture north for pirates and Pink Floyd lasers, make it count—this kind of lineup doesn't come around every week.
