Discover Florida’s 12 Best Islands: Explore Longboat Key
A slender barrier island, Longboat Key is tucked between the Gulf of Mexico and Sarasota Bay.
A slender barrier island, Longboat Key is tucked between the Gulf of Mexico and Sarasota Bay. An abundance of greenery and meticulous landscaping frames its main road, Gulf of Mexico Drive, giving the 11-mile stretch a quiet air of sophistication. Signage and storefronts blend with nature instead of screaming for your attention. The road easily divides this ribbon of land—Gulf-front homes on the west and bayfront properties on the east. It’s not unusual to see bicyclists pedaling along the area’s 10-mile bike path.
On the key’s northwest tip, several access points welcome beachgoers. (A total of 12 dot the island.) Park and follow the path to uncrowded sands, where you’ll find dunes covered with scrub and sea oats instead of shade-casting resorts. In the nearby seaside community of Conrad Beach, homes are valued at a million dollars or more.
Hidden away on the northeast tip of the island is historic Longbeach Village, known for its slower pace and down-home charm. Houses here date back to the 1920s and blend harmoniously with new contemporary structures—as do the village’s restaurants that sit right smack on the edge of Sarasota Bay.
Mar Vista Dockside has the Old Florida flavor of a fishing shack. Tables are scattered on its private beach where trees with string lights create a canopy. A pier makes it easy for boaters to stop in for a beer and mahi-mahi sandwich. Next door, the vibe at Shore is coastal hip. The restaurant’s architecture has a mid-century modern twist, also evident in its interior’s backlit bar and high-top tables lining outdoor patios. Every seat offers views of its 300-foot dock and bay waters. Adjacent is the Shore’s eponymous boutique brimming with cool resort wear from flowing sundresses to leopard-print bikinis.
When it comes to exploring the island’s nature, consider an easy hike through Joan M. Durante Park. A vibrant example of Longboat Key’s conservation efforts, the 32 acres that were once taken over by exotic vegetation have been restored. Boardwalk trails and shell paths weave through thriving mangrove forests, salt marshes and coastal hammock forests along Sarasota Bay.
For those who want to explore surrounding waters, kayak trips with a naturalist or on your own are popular in the morning and at sunset. Happy Paddler’s eco-adventure tours depart from Bayfront Park. visitsarasota.com
A luxury resort stay is the way to go on this island. The Resort at Longboat Key Club delivers a classic private-club experience to its hotel guests. You’re just steps from the beach, 45 holes of golf, and 20 tennis courts. Zota Beach Resort scores for its edgy style, and if you wait until 2023, you can book at the St. Regis.
St. Armands Key
A sister island to Longboat Key, St. Armands Key was the dream of circus tycoon John Ringling in the 1920s. He envisioned a community with homes and stores laid out in a circle. Unfortunately, the stock market crash destroyed his plans, but in the 1940s, St. Armands Circle started to take shape. Today its vibrant mix of upscale, casual boutiques and restaurants attract throngs of visitors.