If you’re lucky enough to be in Sarasota this May, you’re in for a treat. Whether you’re a local looking for weekend plans or dreaming of making Sarasota your forever home, this month is packed with amazing events that showcase the energy, culture, and lifestyle of Florida’s Gulf Coast.

Here’s your curated list of the top events happening around Sarasota in May 2025:

May 3: SUP & RUN 5K at Nathan Benderson Park

Three exciting races kick off at this world-class venue. From paddleboarding to 5K running, enjoy amazing swag, medals, and a fun post-race party.

May 3: Corvettes on the Circle

Car lovers—don’t miss this! Over 150 Corvettes spanning from 1953 to the modern Stingray line up at St. Armand’s Circle for a free, family-friendly event.

May 3–5: Cinco De Mayo Block Party at El Melvin

Three days of live music, street food, LED robot shows, giveaways, and of course—the best margaritas in town.

May 10: Sarasota International Dragon Boat Festival

Get ready for adrenaline-pumping fun on the water. Race day starts at 6:30 a.m. and includes beer gardens, food trucks, wellness vendors, and more.

May 11: Mother’s Day

Celebrate the moms in your life with a beautiful brunch or beach day right here in Sarasota.

May 24: Memorial Day 5K Hike by SRQ VETS

Honor local heroes with a scenic hike across the Ringling Bridge followed by music, food, and community connection at JD Hamel Park.

May 25: AquaPalooza 2025 by MarineMax

Sarasota’s favorite boating event is back! Join the floating party at New Pass Sandbar for live music, sunshine, and water-filled fun.

Sarasota isn’t just a vacation destination—it’s a lifestyle. If you’ve been considering moving to the area, now’s a great time to get familiar with the community and see what it’s all about.

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