Updated November 5, 2026
Grand Central District bars, a Gulfport afternoon, drag and dancing, and brunch. Swap anything out using our full St. Pete & Clearwater Beaches guide.
Saturday
- Afternoon: Wander the Grand Central District shops, then a doughnut at Valkyrie Doughnuts.
- Happy hour: Two-for-ones at COCKtail.
- Dinner: Dinner on Central at Red Mesa Cantina.
- Night: Drag and dancing at The Garage on Central, then Enigma St. Pete.
Sunday
- Brunch: Brunch at The Moon Under Water.
- Afternoon: Head to artsy Gulfport and the beach.
- Evening: Sunset drinks at Undertow Beach Bar.
Before you go
- Sunset is the main event on the Gulf beaches. Pier 60 in Clearwater runs a nightly sunset celebration, and Pass-a-Grille is the classic quieter spot.
- State parks like Fort De Soto, Honeymoon Island and Caladesi charge a park entry or parking fee. Check the official page before you go.
- Many beach bars and boat tours are weather-dependent. Call ahead if the forecast looks rough.
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 budgetTampa with kidsYbor City nightsTampa food lover's weekendRainy-day TampaSiesta Key beach weekendSlow 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