Updated November 5, 2026
Powder-white sand, drum circles, parasailing and the island's best oyster bar. Swap anything out using our full Sarasota & Anna Maria Island guide.
Saturday
- Morning: Claim your spot on Siesta Beach.
- Afternoon: Go up with Siesta Key Watersports - Parasailing.
- Happy hour: Live music at Siesta Key Oyster Bar (SKOB).
- Night: Frozen drinks at Daiquiri Deck - Siesta Key Village and Beach Club Siesta Key.
Sunday
- Morning: Paddle the mangrove tunnels with Sea Life Kayak Adventures - Lido Key Mangrove Tunnels.
- Lunch: Siesta Key Village cafes.
- Evening: Shop and dine on St. Armands Circle.
Before you go
- Siesta Beach parking fills early on weekends. Arrive before 10 a.m. or use a rideshare.
- Some piers and attractions are still being rebuilt after the 2024 hurricanes. Confirm hours on the official site before you drive out.
- Venice, about 30 minutes south of Sarasota, is known for shark-tooth hunting at Caspersen and Venice beaches.
Other weekend plans
A weekend in St. Pete Beach and ClearwaterA weekend in TampaA weekend in Sarasota and Anna Maria IslandAn Orlando weekend from Tampa BayA romantic St. Pete weekendClearwater Beach with kidsGulf beach bar hopSt. Pete nights outTarpon Springs & DunedinBeach weekend on a budgetLGBTQ+ weekend in St. PeteTampa with kidsYbor City nightsTampa food lover's weekendRainy-day TampaSlow weekend on Anna Maria IslandSarasota arts weekendWild SarasotaeFoil & water adventure weekendOrlando for grown-upsLGBTQ+ weekend in OrlandoOrlando's wild sideRockets & racing: a Space Coast dayOrlando live music weekendSwim with manatees in Crystal RiverFlorida springs road tripOne perfect day: Tampa to the beach