6402 Lakewood Ranch Blvd, Lakewood Ranch, FL 34202

A casual, unstructured way to play tennis — participants organize their own games and matchups.

1561 Lakefront Drive, Sarasota, FL 34240

Join Florida Provisions every Monday for Bingo Night — cold beer and prizes.

1570 Lakefront Drive, Sarasota, FL 34240

Gather your friends, challenge your brain, and savor a beer at Good Liquid Brewing Company for Trivia Night every Monday.

5304 Holmes Blvd, Holmes Beach, FL 34217

Sing your heart out every Monday at The Freckled Fin Irish Pub on Anna Maria Island.

8130 Lakewood Main Street, Suite 104, Bradenton, FL 34202

A night of singing, dancing, and prizes set to your favorite hits, paired with scratch-kitchen food, handcrafted cocktails, and craft beer.

10719 Rodeo Dr, Lakewood Ranch, FL

Hosted by Steve-O, general trivia covering current events, sports, holidays, and more — compete for bragging rights, pitchers of beer, and gift cards.

1561 Lakefront Drive, Suite 102 and 103, Sarasota, FL 34240

A laid-back night of singing your favorite songs, cheering on friends, and half-off margaritas.

10719 Rodeo Dr, Lakewood Ranch, FL 34202

Free Texas Hold 'Em — no cost to play. Weekly winner takes home a $50 Ed's gift card, plus a chance at a seat in the One-Eyed Jacks tournament at Sarasota Kennel Club.

6402 Lakewood Ranch Blvd, Lakewood Ranch, FL 34202

A casual, unstructured way to play tennis — participants organize their own games and matchups.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

Bradenton Riverwalk

A relaxed group walk along the river with a social meetup after.

7301 Island Cove Terrace, Lakewood Ranch, FL 34240

Roulette-style pickup volleyball for players ready to jump in and play without instruction.

7500 Island Cove Terrace, Sarasota, FL 34240

A fun morning of casual cornhole for all skill levels — grab a partner or go solo, beanbags and boards provided.

Floridays Woodfire Grill & Bar, 12332 Manatee Ave W, Bradenton, FL 34209

Enjoy live music by various artists every Thursday and Saturday evening at Floridays Woodfire Grill & Bar.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

Near Spanish Rocks, Holmes Beach, FL 34217 (park near 33rd Street, or at Manatee Public Beach and walk left along the beach)

A weekly gathering for drumming, dancing, and community as the sun goes down on Anna Maria Island. The circle begins one hour before sunset, so the exact start time shifts through the season.

Downtown Sarasota, Lemon Ave

Fresh produce, local vendors, and live music in the heart of downtown.

Palmetto

A dozen local food trucks, live music, and family-friendly activities.

Floridays Woodfire Grill & Bar, 12332 Manatee Ave W, Bradenton, FL 34209

Enjoy live music by various artists every Thursday and Saturday evening at Floridays Woodfire Grill & Bar.

Lakewood Ranch Main Street, Lakewood Ranch, FL

Local produce, baked goods, and live music every Sunday at Lakewood Ranch Main Street.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

3115 Lakewood Ranch Blvd, Suite 110, Bradenton, FL 34211

A relaxed Sunday afternoon with a food truck (2-6 PM) and open mic featuring local musicians and performers (3-6 PM). Tours and tastings available 12-3 PM by reservation.

Siesta Beach, 948 Beach Rd, Sarasota, FL 34242

A vibrant weekly drum circle on Siesta Beach every Sunday evening, beginning an hour before sunset. Locals and visitors gather for rhythm, dancing, and sunset on the sand.