Top Sarasota Weekend Events | May 16–17, 2026
Darren Dowling
Darren Dowling
Mid-May brings another exciting weekend to Florida’s Gulf Coast with a wide variety of events happening across Sarasota, Lakewood Ranch, Siesta Key, Venice, and Bradenton. Whether you enjoy outdoor sports, family-friendly activities, local markets, or sunset beach traditions, there’s something happening for everyone this weekend.
📍 Siesta Key Beach
📅 May 16, 2026 | Starts 9 AM
One of the most energetic sporting events on Siesta Key returns this May with competitive men’s and women’s rugby teams battling it out directly on the sand. The tournament combines exciting athletic competition with live music, food vendors, beachside entertainment, and a lively community atmosphere.
The event is free for spectators and makes for a great all-day outing near Sarasota’s world-famous white sand beaches.
👉 Event Info:
https://www.siesta7s.com
📍 LECOM Park
📅 May 16, 2026 | Game Starts 6:30 PM
Baseball meets sci-fi fun during the Bradenton Marauders’ themed Star Wars Night. Fans can enjoy character appearances, themed entertainment, special jerseys, and a post-game fireworks show.
LECOM Park, one of Florida’s historic ballparks, creates the perfect setting for a fun family night out just north of Sarasota.
👉 Tickets & Info:
https://www.milb.com/bradenton
📍 Sahib Shrine Auditorium
📅 May 16, 2026 | 9 AM – 4 PM
Animal lovers and families can explore reptiles and exotic animals from around the world at Reptiday Sarasota. The event features educational exhibits, reptile experts, vendors, and interactive experiences suitable for all ages.
This unique indoor event has become a popular stop for families looking for something different to do around Sarasota.
👉 Event Details:
https://repticon.com/florida/reptiday-sarasota/
📍 Big Top Brewing Company
📅 May 17, 2026 | 10:30 AM – 1:30 PM
Classic car lovers can enjoy a relaxed Sunday event featuring vintage cars, custom vehicles, specialty builds, food, drinks, and community gathering space at Big Top Brewing Company.
The combination of local craft beverages and automotive culture makes this a fun social event for both enthusiasts and casual visitors.
👉 Event Info:
https://carcruisefinder.com/florida-car-shows/event/beckers-car-show/
📍 Waterside Place
📅 May 17, 2026 | 10 AM – 2 PM
One of the area’s most popular weekly markets, the Farmers Market at Lakewood Ranch features fresh produce, artisan foods, handmade goods, live music, and family-friendly activities along the scenic Waterside district.
It’s a perfect Sunday stop for shopping local while enjoying the Lakewood Ranch lifestyle.
👉 Learn More:
https://watersideplace.com
📍 Siesta Beach
📅 May 17, 2026 | Around Sunset
One of Sarasota’s most iconic weekly traditions, the Siesta Key Drum Circle brings together locals and visitors for drumming, dancing, music, and sunset celebrations directly on the beach.
This long-running community gathering captures the relaxed and creative spirit that makes Sarasota’s beach culture so unique.
👉 Visitor Info:
https://www.siestakeychamber.com/drum-circle/
From beach tournaments and baseball games to farmers markets and waterfront sunsets, this weekend reflects the vibrant Gulf Coast lifestyle that continues to attract residents and visitors to Sarasota, Lakewood Ranch, Venice, and Bradenton.
If you’re considering buying or selling real estate in the Sarasota area, local expertise can help you make the most of the opportunities available throughout the region.
Beyond Realty
2170 Main Street, Suite 103
Sarasota, FL 34237
941-204-0493
Darren Dowling is a Sarasota-based broker-owner specializing in Sarasota, Lakewood Ranch, and Gulf Coast residential real estate, relocation, and new construction opportunities.
Why homeownership continues to outperform other investments and what it means for buyers and homeowners across Sarasota, Lakewood Ranch, Manatee County, and Charlotte … Read more
Inventory east of I-75 collapsed 46% — yet homes take 64 days to sell and half the listings cut price. Here's what's really happening.
Punta Gorda, Port Charlotte, and Englewood just posted the strongest price growth in Southwest Florida — while nobody was watching.
The median dipped 3.8% — but the average price rose, sellers kept 95.4% of asking, and contracts jumped 19%. Here's the real story.
The official May 2026 SunStats numbers are in — here's what they mean if you're buying or selling in Sarasota County this year.
You’ve got questions and we can’t wait to answer them.
