SR 50 · One-day road trip

Winter Garden to the Gulf: skateparks & weird Florida

One road, one day. SR 50 runs straight west and dead-ends at the Gulf in Bayport. No I-4, no Tampa traffic, just every skatepark and weird roadside stop along the way.

The itinerary

Read before you go

Boyett's Grove is open weekends only. May-Stringer House is open Tue–Sat, 11 AM–3 PM.

Saturday is the only day you can hit everything. On a Sunday, skip May-Stringer. On a weekday, skip Boyett's.

Too packed? Cut Showcase of Citrus (about 1.5 hr with the detour) and start at the Citrus Tower instead.

Ranked by weirdness

  1. Weeki Wachee mermaids: underwater shows since 1947.
  2. Pink Dinosaur: a giant pink dinosaur. That's it.
  3. Showcase of Citrus: monster-bus safari with camels.
  4. Boyett's Grove: 1960s tourist trap, frozen in time.
  5. May-Stringer House: haunted Victorian. Ask about the attic.
  6. Coney Island Drive Inn: Elvis ate here.
  7. Silver Dolphin: turtles, quarters, a baby gator.

Skatepark notes

  • Ocoee: best warm-up. Open until 10 PM, so it works on the drive home too.
  • Lake David: small, and the metal ramps get brutally hot at midday.
  • Pioneer Park: strongest park on the Gulf end, lit until 9 PM.

Left out: Independence Skate Spot (detour south, barely a park). Bushnell and Beverly Hills are too far off route.

Tips

  • Pine Island's lot is small ($5–8). On weekends, arrive by late afternoon. It closes right at sunset.
  • Want a bigger beach? Clearwater or Honeymoon Island are 20–30 min farther, via the busier I-4/Tampa route.
  • Chill version: Plant St. Market for coffee, Lakeridge Winery (free tour, 10 min north of the Citrus Tower), and Historic Bayport Park to watch for manatees.