We’ll soon bid farewell to April and its packed lineup of local events, and while we’ll undoubtedly start to feel the slowdown of off-season here in May, there’ll still be numerous notable happenings that month in the Sarasota area.
The Memorial Day parade in downtown Sarasota will be one of multiple events marking occasions such as Cinco de Mayo, the Kentucky Derby and — a month early — Pride.
There’ll also be a day of boating and partying at AquaPalooza, as well as another event centered around a vehicle (Corvettes on the Circle) and another notable party (the second-to-last Fresh Friday this season in downtown Sarasota.) Van Wezel Performing Arts Hall will host major names in comedy and jazz, while other celebrities in the worlds of sports and journalism will take part in an annual gala funding cancer research.
Here are the 10 biggest events taking place in the Sarasota area in May, presented in chronological order. Event details are subject to change.
Fresh Fridays
The popular monthly street party series in downtown Sarasota will feature a Back to the ’80s-themed edition in May — its second-to-last event of this season — with a live band playing ’80s hits and attendees encouraged to come dressed up in their best ’80s-inspired look. 7-10 p.m. May 1; South Palm Avenue, Sarasota; free admission; downtownsarasotadid.com/fresh-fridays
Dick Vitale Gala
ESPN Hall of Famer and Lakewood Ranch resident Dick Vitale, who recently announced a new melanoma diagnosis, holds this 21st annual gala raising money for cancer research. This year’s honorees include UConn women’s basketball head coach Geno Auriemma, journalist Katie Couric, University of Houston men’s basketball head coach Kelvin Sampson, cancer survivor and John Saunders Courage Award Honoree Jamie Valvano, and Michigan State University men’s basketball head coach and Dick Vitale Spirit Award Honoree Tom Izzo. ESPN’s “SportsCenter” anchor Kevin Negandhi emcees. May 1; The Ritz-Carlton, Sarasota, 1111 Ritz Carlton Drive, Sarasota; $1,500 individual ticket; 941-350-0580; v.org/event/dick-vitale-gala
Corvettes on the Circle
The 28th anniversary show will feature more than 150 models, ranging from the classic 1953 C1 to the newest models, with trophies awarded to the top three Corvettes in each generational class, as well as Best in Show and Skyway Corvette Club Favorite. 9 a.m.-3 p.m. May 2; St. Armands Circle Park, 1 St. Armands Circle, Sarasota; free spectators, $50 advance, $60 day of (participants); 941-993-4201; starmandscircleassoc.com
Taste & Toast Gulf Coast
The second annual event will feature tastings from chefs and local eateries; more than 20 wineries, breweries, and cocktail and mocktail purveyors; Kentucky Derby bourbon tasting and live watch party; Cool Zone Casino; live entertainment and more. Proceeds will benefit Florida Restaurant & Lodging Association Suncoast Chapter Education initiatives. 5 p.m. VIP, 6 p.m. general admission May 2; Palmetto Marriott Resort & Spa, 600 U.S. 41 N., Palmetto; $95, $150 VIP (ages 21 and up only); tasteandtoastgulfcoast.com
Jerry Seinfeld
The stand-up comedian and star of “Seinfeld,” regularly considered one of the greatest television shows of all time, is always one of Van Wezel Performing Arts Hall’s most in-demand acts and he returns to the Sarasota venue for two shows in May. 5 and 8 p.m. May 2; Van Wezel Performing Arts Hall, 777 N. Tamiami Trail, Sarasota; both shows sold out as of press time; 941-263-6799; vanwezel.org
Cinco de Mayo Block Party at Rocco’s Tacos
With downtown Sarasota’s Circo: A Taco & Bourbon Joint and El Melvin Cocina Mexicana now closed, there are fewer local options for Cinco de Mayo block parties this year. Thankfully, there’s still Rocco’s Tacos, the West Palm Beach-founded restaurant that opened in University Town Center in 2023. Its various locations, including UTC, will be once again holding all-day Cinco de Mayo block parties. 11 a.m.-11:30 p.m. May 5; Rocco’s Tacos & Tequila Bar, 243 N. Cattlemen Road, Sarasota; 941-477-8226; roccostacos.com
Be Fabulous Music & Arts Pride Fest
The three-day festival will include the May 7 opening night art exhibition “Still We Rise: Queer and Trans Defiance,” May 8 Tea4T Drag Pride edition and May 9 full-day concert featuring bands including MeteorEYES, Lesa Silvermore Band, Sorry Barb and The Tilt. 6-10 p.m. May 7; 925 Maddox Gallery & Studios, 925 N. Lime Ave., Sarasota; free; 9-11:30 p.m. May 8; 925 Maddox Gallery & Studios, 925 N. Lime Ave., Sarasota; $11.44-$12.51 (ages 18 and up); 3-10 p.m. May 9; Five Points Park, 1 Central Ave., Sarasota; fabaf.org
Herbie Hancock
A renowned jazz musician both for his work with groups including the Miles Davis Quintet and as a bandleader, Herbie Hancock’s accolades include 14 competitive Grammys (including Album of the Year for 2007’s “River: The Joni Letters”) and a Grammy Lifetime Achievement Award, an Oscar (for his score to the 1986 film “‘Round Midnight”) and NEA Jazz Masters. 7 p.m. May 9; Van Wezel Performing Arts Hall, 777 N. Tamiami Trail, Sarasota; $81-$126; 941-263-6799; vanwezel.org
AquaPalooza
The Memorial Day weekend kickoff and day of boating, music, and fun has boats gather and anchor together to listen to live music from Jah Movement, Dr. Dave Band, and Zach Regan and the 776. The party will be at New Pass Sandbar, in front of MarineMax’s marina. 10 a.m.-4 p.m. May 24; MarineMax, 1601 Ken Thompson Parkway, Sarasota; free; 941-388-4411; eventbrite.com
Downtown Sarasota Memorial Day Parade
The annual Memorial Day parade is expected to start at Main Street and Osprey Avenue, traveling down Main Street and concluding at Chaplain J.D. Hamel Park, where a ceremony will be held at 11 a.m. 10 a.m. May 25; Main Street, Sarasota
Email entertainment reporter Jimmy Geurts at jimmy.geurts@heraldtribune.com. Support local journalism by subscribing.
This article originally appeared on Sarasota Herald-Tribune: 10 biggest May events in Sarasota area you won’t want to miss
Reporting by Jimmy Geurts, Sarasota Herald-Tribune / Sarasota Herald-Tribune
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