What’s Happening in Sarasota This May – The Perfect Time to Explore Sarasota
May is one of Sarasota’s best-kept secrets. In fact, with sunny skies, warm breezes, and fewer crowds, it’s the perfect time to enjoy the city’s beauty, culture, and charm. Whether you’re a local, a snowbird, or exploring Sarasota as your future home, May offers something for everyone.
Looking for things to do in Sarasota in May? Fortunately, from local markets and brunches to the Gracewater Amenity Center groundbreaking, there’s no better time to experience it all.
Ideal Weather, Fewer Crowds
May in Sarasota brings highs in the low 80s and evenings that are perfect for al fresco dining or sunset strolls. In addition, the spring break rush has passed, yet the city remains alive with seasonal brunches, fresh local markets, and community events you won’t want to miss.
What’s Happening in Sarasota This May
May 3 – Corvettes on the Circle
To kick off the month, St. Armands Circle transforms into a car enthusiast’s dream during the 27th Annual Corvette show. From 9 a.m. to 3 p.m., view over 150 classic and modern models, enjoy live music, and explore the shops and restaurants of St. Armands.
May 3–5 – El Melvin’s Cinco De Mayo Block Party
Later that same weekend, Downtown Sarasota will come alive for Cinco De Mayo weekend with El Melvin Mexican Restaurant’s three-day block party. Additionally, there will be live music, outdoor bars, gourmet street food, LED performers, and giveaways, it’s a festive celebration open to all. Admission is free and VIP tables are available.
May 11 – Mother’s Day Brunches
Sarasota offers several standout options to make this Mother’s Day unforgettable:
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First, the St. Regis Longboat Key will host a stunning brunch from 11 a.m. to 2 p.m., complete with live music and elaborate food stations in a luxurious beachfront setting.
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Meanwhile, the Ritz-Carlton Sarasota, located minutes from Gracewater, offers an extravagant holiday buffet that’s perfect for celebrating in style.
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Finally, Selby Gardens will host its annual Mother’s Day Brunch with three seating times and a buffet by Michael’s on East, including carving stations, a pancake bar, and access to their spring exhibit.
May 15 – Gracewater Amenity Center Groundbreaking
Mid-month marks an exciting milestone for our Gracewater community. We officially break ground on our highly anticipated Amenity Center, which will feature a resort-style pool, gathering spaces, and lifestyle features designed for relaxation and connection.
Without a doubt, it’s the beginning of something truly special for our future residents.
May 18 – Sarasota International Dragon Boat Festival
Held at Nathan Benderson Park, this vibrant festival features teams from across the region racing in ornate dragon boats. With food trucks, entertainment, and scenic views, it’s a fun-filled event for the whole family just minutes from Gracewater.
May 26 – Sarasota Memorial Day Parade and Ceremony
To end the month on a meaningful note, honor those who served during Sarasota’s annual Memorial Day Parade, beginning at 10:00 a.m. at the intersection of Osprey and Main Street.
Weekly Saturdays – Sarasota Farmers Market
Every Saturday, the downtown Sarasota Farmers Market offers fresh produce, handmade goods, live music, and artisan vendor. It’s a perfect start to the weekend and only a short drive from Gracewater.
Weekly Thursdays – Sunsets at The Bay Park
Each Thursday evening, The Bay Park hosts free live music during golden hour along Sarasota Bay. It’s a relaxing, family-friendly way to end the day and take in one of the area’s most beautiful sunset spots.
Why Gracewater is the Perfect Home Base
Gracewater at Sarasota is ideally located just west of I-75, giving you peaceful, resort-style living with easy access to everything that makes Sarasota special. Whether you’re beaching it on a Sunday, attending a downtown festival, or enjoying sunset concerts on the bay, Gracewater puts you in the center of it all.
What residents love:
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Our resort-style pool and the new Amenity Center breaking ground this May
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Smart home features and thoughtfully designed layouts
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Proximity to downtown Sarasota, beaches, dining, and cultural attractions
Live Where Others Vacation
With so much happening this month, May is the perfect time to discover Sarasota — and explore what life could look like at Gracewater. Schedule a private tour of our homes or download our Insider’s Guide to Sarasota’s Best Attractions and start planning your adventure.
Interested in living in our community? Explore our available homes at Gracewater
