Rent The Keys Blog

If you’ve never stood on Siesta Beach on a Sunday evening with several hundred strangers, a couple dozen drummers, and a slow-fading orange sky in front of you — clear a weekend this summer and fix that. The Siesta Key Drum Circle runs every Sunday, year-round, and it remains one of the most quietly perfect rituals on the Gulf Coast. What It Is A free, informal gathering on Siesta Beach...

Sarasota earned the “Circus City” nickname for a reason — and every summer, the Circus Arts Conservatory and The Ringling team up to put it on full display inside the air-conditioned, perfectly intimate Historic Asolo Theater. The Summer Circus Spectacular is back for its 2026 run, on stage from June 13 through August 8, 2026, and if you’ve never made the drive over for a show, this is the year....

If you’ve spent a Fourth of July anywhere on the Gulf Coast, you know there’s no shortage of fireworks shows. But there’s only one place along our stretch of beaches that turns the entire island into a rolling, water-gun-soaked, bead-throwing celebration of the holiday — and that’s Anna Maria Island, when the Anna Maria Privateers roll out their annual 4th of July Parade. This year it lands on Saturday, July...

Your Ultimate Guide to the Sarasota Downtown Foodie World Asian Food Festival 2026 Get ready, Sarasota — one of Florida’s most exciting culinary celebrations is coming to the waterfront this June! The Sarasota Downtown Foodie World Asian Food Festival is set to take over J.D. Hamel Park from June 5–7, 2026, bringing 80+ food vendors, live entertainment, cultural performances, and a dazzling night market experience to the heart of downtown...

If you have never spent a July Saturday on Pine Island chasing down a tray of mango ice cream, this is the year to fix that. The MangoMania Tropical Fruit Festival returns to 9940 Stringfellow Road in St. James City on Saturday, July 11, 2026, hosted by the Greater Pine Island Chamber of Commerce. It runs 9:00 AM to 5:00 PM and is the kind of small-island summer festival that,...

The Cape’s biggest night of the summer is back. Red, White & BOOM! returns to Bernice Braden Park on Saturday, July 4, 2026 for an all-evening, all-free Independence Day celebration — culminating in what’s regularly billed as the largest fireworks show on Florida’s southwest coast. If you’ve ever wondered why locals start asking about beach-house bookings the moment April rolls around, this is one of the reasons. Plant yourself in...

Every year, the Venice Symphony turns Memorial Day weekend into the kind of event that ends up in your photo album for years. Star Spangled Spectacular: A Patriotic Pops Concert returns to CoolToday Park on Saturday, May 23, 2026, and it remains one of our absolute favorite ways to kick off summer on the Gulf Coast. If you came to last year’s “Salute to the Greatest Generation,” you know the...

Plenty of people fly into Sarasota for the beach. Some come for the music. And once a year, a different crowd shows up — capes packed, foam swords stowed in checked bags — for SiestaCon, Sarasota’s homegrown comic book and pop culture convention. SiestaCon 2026 lands at Robarts Arena on Saturday, May 9, and if you’ve got kids in the comics-and-cosplay age range (roughly 6 to 16, but really, ageless),...

If you’ve spent any time in downtown Sarasota on a Saturday night in early May, you already know the secret: the streets close, the string lights come on, and what looks like a quiet stretch of Main Street turns into one of the best block parties on the Gulf Coast. Rock De Mayo is back on Saturday, May 5, 2026, and it’s absolutely worth building a long weekend around. What...

An Unforgettable Day of Racing, Culture, and Community Spirit Mark your calendars — the Sarasota International Dragon Boat Festival is returning to the breathtaking Nathan Benderson Park on Saturday, April 18, 2026! This premier paddling event is one of the most exciting outdoor festivals on Florida’s Gulf Coast, drawing competitive athletes, recreational paddlers, families, and spectators from across the country for a full day of high-energy racing, cultural celebration, and...