The Local Lowdown on Osprey, Nokomis & Casey Key

A drive down Tamiami Trail yields a bevy of eateries, natural landmarks, kayak launches, tiki bars, tackle and dive shops, and more throughout the cities of Osprey and Nokomis. Meanwhile, Casey Key's more private stretches boast extravagant homes and one two-way road that that hugs the serene shoreline — perfect for cycling or cruising.

This quiet slice of Florida's Gulf Coast is great for a romantic getaway, an outdoor family adventure or simply a slower pace beyond the beaten path.

Osprey: History, Nature & Dining

Historic Spanish Point

Spanning 30 lush acres in Osprey, Historic Spanish Point is an “outdoor archaeological and historic museum” on Little Sarasota Bay. Visitors can kayak or paddleboard through the waters the Native Americans traveled 5,000 years ago. Magical experiences include the Jungle Walk, the Sunken Garden and one of the largest butterfly gardens on the Gulf Coast. 

Visitors can take a daily docent-led tour and connect with the real Old Florida, where native flora and fauna intermingle with historic buildings and an archaeological site. Big Waters Land Trust protects the property, ensuring the land remains a natural Florida splendor.

Oscar Scherer State Park

With its 15 miles of trails surrounded by scrubby flatwoods, Oscar Scherer State Park in Osprey is one of the best spots in Southwest Florida for viewing scrub jays (a native endangered bird). The park also has swimming, picnicking, hiking, camping/glamping and wildlife viewing opportunities. Canoeists and kayakers can rent vessels to paddle along South Creek, a tidal blackwater stream, while geo-seekers can go on a geocache treasure hunt through Oscar Scherer's lush forestry. 

The state park also features 10 miles of biking trails, with the Legacy Trail cutting directly through the heart of the park. The multi-use recreational trail goes from the beaches of Venice north to Sarasota, with the park located directly in the middle. 

Fine Dining to Tiki Bar Hopping

With an idyllic setting on 3 acres of a former historic estate, Roessler’s Restaurant has been an anniversary and wedding proposal destination for the last four decades. The menu retains its longtime flair, and regulars return for sautéed veal sweetbreads, crêpes Suzette, Wiener Schnitzel Holstein, Snapper Pontchartrain and the restaurant’s famous escargot.

Just down the road, boaters and beachgoers let loose under the tiki-thatched roofs of Evie's at Spanish Point and Casey Key Fish House after a day in the sun and saltwater. Tiki bar culture is strong here, with strong drinks, live music and fun-loving Florida vibes to go around. Enjoy beautiful bayfront views, fresh-caught seafood favorites and getting to know the locals. 

Nokomis: Beaches, Boating & Local Flavor

Nokomis Beach & North Jetty

Nokomis Beach is Sarasota's oldest public beach, located on the barrier island of Casey Key. It offers a laid-back, family-friendly vibe, free parking, year-round lifeguards, a midcentury pavilion listed on the National Register of Historic Places and a vibrant drum circle on Wednesdays and Saturdays. For refreshments, beachgoers can grab drinks and bites at the concession.

The area also offers picnicking, boating, paddleboarding, volleyball and more. At the end is North Jetty Beach, a popular spot for fishing from the rocks and, under the right conditions, surfing the gentle Gulf waves. Rent a paddleboard or kayak here from Jetty Kayak Rentals. 

As the sun sets over the Gulf, take a long beach walk, join a free yoga flow or vibrant weekly drum circle—the perfect preludes to curling up in a coastal cottage.

Days on the Water

There are a number of local outfitters to help you get out on the water in Nokomis. Hit up Cool Breeze Boats & Jet Ski Rentals for boating, kayaking and jet skiing rentals; Casey Key Tiki Tours for sunrise and sunset tiki cruises; Suncoast Marine Tours for a more luxurious boat day out to the sandbars; Seas the Day Charters for exciting dolphin-watching tours; Reel Rebels Fishing Adventures for offshore fishing charters; and more. There's no shortage of ways to get out and have fun on the water in Nokomis.

Longtime Local Dining

Pop's Sunset Grill is one of those must-go places if you're passing through or staying in Nokomis. For locals, it's the spot they bring out-of-town visitors to, if that tells you something. Located on the Intracoastal Waterway, Pop's pairs fresh Florida seafood with front-row sunset views and a lively waterfront atmosphere. Arrive by boat or car to enjoy Gulf Coast classics like grouper sandwiches, peel-and-eat shrimp and tropical cocktails while live music sets the soundtrack. 

Nearby, Cafe Evergreen is a mom-and-pop (or, more accurately, husband-and-wife) restaurant nestled in Nokomis just south of Roberts Bay. Housed in a former bank built in 1920, this place has been a longstanding favorite for locals for the last decade-plus. Refuel with fresh juice blends or health-forward food options, or classic favorites like a burger and sweet potato fries. With a passion for locally sourced, organic ingredients across the menu, this is one of those rare places you'll feel better walking out of than you did walking in.

Casey Key: Peaceful Biking & Shelling

Casey Key is a secluded, narrow 8-mile barrier island offering a laid-back Gulf Coast escape with an air of luxury. Often touted as Sarasota’s hidden gem, this area is beloved for its gorgeous mansions and celebrity estates.  

Bicycle Rides

Spend the day cruising the scenic stretch of road that tightly hugs the coastline of Casey Key, including winding, tree-lined bends that open up to spectacular Gulf views. 

Visitors can rent beach cruisers or e-bikes at Voltaire Cycles in nearby Osprey to cycle down Casey Key Road, the only thoroughfare. If you have a car, it's just as magical taking a leisurely drive beside the canopy of sea grapes and palms and admiring the beautiful homes. You can enter via two bridges: Albee Road from the south (near Venice) or Blackburn Point Road from the north (via a historic one-lane swing bridge).

Secluded Shells

The key sits between the Intracoastal and the Gulf, and beach access is only available near the southern tip of the island as it connects to Nokomis. If you check in to a Casey Key hotel, enjoy beach access during your stay for shell combing Florida seashells along quiet, uncrowded stretches of shoreline. Due to the area's exclusive nature, you won't be sifting through picked-over piles of shells like other popular destinations. 

Where to Stay & How to Explore

While you won't find many big-name hotel brands in this Osprey, Nokomis and Casey Key area of Sarasota, there are plenty of Old Florida bungalows and villas to rent, plus local inns and boutique beachfront resorts. Check out accommodations here. 

Once you've locked in your stay, opt into the Neighborhood Navigator Pass to dive into Sarasota’s many communities, discovering local eateries, boutiques, cultural hotspots and more!