Osprey, FL

Osprey's history runs back thousands of years. Historic Spanish Point sits on one of the largest intact prehistoric sites on Florida's Gulf Coast, with an archaeological record of about 5,000 years — Native people lived on the shell mounds along Little Sarasota Bay from roughly 5,900 years ago until sometime before 1100 AD. The modern story begins in 1867, when John Green Webb and his family moved down from Utica, New York, under the Federal Homestead Act. A Spanish trader in Key West had tipped them off to a fertile high point of land on the bay — they named their homestead Spanish Point in his honor.

The Webbs grew citrus, sugar cane, and vegetables, built a packing house that still stands, and turned their place into Webb's Winter Resort, welcoming visitors and scientists. Pioneer John Webb also named the local post office after the fish-hawk, the osprey — and that's how the community got its name. In 1910, Bertha Palmer bought the Spanish Point homestead and made it the centerpiece of her 350-acre winter estate, which she called Osprey Point. She preserved the pioneer buildings and connected them with formal gardens — the Sunken Garden, Duchene Lawn, and Jungle Walk — that visitors can still walk today. Her family kept the property until 1980, when they donated it; it's now operated by Marie Selby Botanical Gardens.

Historic Spanish Point is listed on the National Register of Historic Places and stands as one of the top few percent of U.S. museums by accreditation. Osprey also claims a quirky agricultural footnote: John Webb was growing bananas nine years before they were introduced to the general public at the 1876 Centennial Exhibition in Philadelphia.

• Historic Spanish Point — 30-acre bayfront museum and garden site (part of Marie Selby Botanical Gardens) with prehistoric shell middens, a pioneer homestead, and nature trails.
• Oscar Scherer State Park — 1,400-acre state park with 15 miles of hiking and biking trails, kayaking on South Creek, camping, and Florida scrub-jay habitat.
• Legacy Trail through Osprey — paved trail segment connecting Osprey to Sarasota and Venice for biking and walking.
• Blackburn Point Park — waterfront park on Little Sarasota Bay with a boat ramp and Intracoastal views.
• Evie's at Spanish Point — tiki bar on Little Sarasota Bay with live music, dock access for boaters, and sunset views.
• Osprey Archeological and Historic Site — protected archaeological site within the Historic Spanish Point area.
• In nearby Venice: Venice Beach and the Venice Fishing Pier — Gulf beaches and pier a few miles south.
• In nearby Sarasota: Marie Selby Botanical Gardens — tropical gardens on Sarasota Bay.