Gulf Coast Getaway: Sarasota & Longboat Key

Whether you’re here for a laid-back weekend or a longer getaway, Sarasota and Longboat Key offer so much more than just beautiful beaches (though those are reason enough to visit). From local art and fascinating history to charming shopping districts and unforgettable coastal adventures, there’s no shortage of ways to fill your days. Here are a few of my favorite ways to spend time on Florida’s gorgeous Gulf Coast.

Art and culture

Start your day by stepping back in time at the magnificent winter estate of John and Mable Ringling—yes, those Ringlings, of circus fame. Their home, Ca’ d’Zan, is a breathtaking 36,000-square-foot Mediterranean-style mansion built as a coastal escape from Wisconsin winters and designed for lavish entertaining during the Roaring Twenties. After a guided tour through its opulent rooms and sweeping terraces, wander the 66-acre grounds, where you’ll find dramatic banyan trees and gardens Mable herself once tended.

The on-site Circus Museum offers a fascinating glimpse into the golden age of “The Greatest Show on Earth,” while the Ringling Museum of Art showcases an impressive collection ranging from Old Masters to contemporary works, with visiting exhibitions and pieces by talented Florida artists.

St. Armand’s Circle

No visit to Sarasota is complete without a stop at St. Armands Circle, often called the “Jewel of Sarasota.” This lively outdoor district is home to more than 100 shops, art galleries, and restaurants—perfect for an afternoon of browsing, dining, and people-watching. Grab a bite at one of the charming cafés, pick up something special at a local boutique, and enjoy the lush tropical landscaping that makes the circle such a beloved local landmark.

Beaches

The Gulf Coast’s powder-white sand beaches are regularly ranked among the best in the United States—and it’s easy to see why. The barrier islands of Lido Key, Siesta Key, and Longboat Key each offer their own slice of coastal paradise, from family-friendly public beaches to peaceful spots perfect for sunset picnics. Spend your days kayaking through mangrove tunnels, spotting dolphins on a private sunset cruise, or simply soaking up the sun on the soft, sugar-white sand.

One of the best parts of any getaway is the food—and here, the Gulf itself is often the star of the plate. From trendy but casual rooftop bars to historic landmarks and fine-dining favorites, the region’s restaurants celebrate local seafood, seasonal ingredients, and those signature coastal sunsets that make every meal feel like a special occasion.

• Indigenous: Tucked away in a quiet neighborhood, this charming restaurant has been serving sustainably sourced seafood and locally inspired dishes since 2011. The menu changes weekly to highlight what’s fresh and in season, and the setting—a beautifully restored home with both indoor and outdoor seating—feels intimate and special. (Note: wine and beer only.)

• Jack Dusty: Located inside The Ritz-Carlton and open to all, Jack Dusty is a vibrant spot for breakfast, lunch, or dinner. A lively bar scene and a focus on local seafood make it a favorite among hotel guests, locals, and visitors alike. It’s the kind of place where you can enjoy a leisurely meal or simply sip a cocktail while watching the world go by on this waterfront location.

• Ocean Prime: This Florida-based seafood and steakhouse chain has made a splash in Sarasota with its new waterfront location at The Quay, a 14-acre dining and entertainment destination. Expect polished service, high-quality seafood, and sweeping water views—perfect for a celebratory dinner or night out.

• Oshen: Head to the rooftop at the new St. Regis for a truly memorable evening at Oshen, a Japanese-Peruvian fusion bar known for handcrafted rolls and creative cocktails. Time your visit for sunset—the dimmed lights protect nesting sea turtles, and the view over the Gulf is spectacular, especially with a drink in hand. Note the property is open to hotel guests only.

• The Columbia: A Florida icon since 1905, The Columbia is a must-visit at St. Armands Circle. The original Tampa location is the oldest Spanish restaurant in the United States and the longest continuously operating restaurant in Florida. This outpost offers the same beloved classics—the legendary 1905 Salad, Cuban sandwich with gazpacho, and deviled crab croquettes—all served in a lively, history-filled setting. Order a mojito, settle in, and savor a taste of old Florida.

• Shore: Shore is a local favorite known for its “cool vibe and delicious eats.” Expect fresh seafood, inventive cocktails, and breezy coastal views—plus a stylish in-house clothing line if you’re in the mood to shop before or after your meal.

• CW Prime: Located inside the new St. Regis, CW Prime is a Wine Spectator—recognized restaurant known for its expertly prepared steaks, fresh seafood, and elegant, modern setting. For an extra-special experience, request a table in the Spirits Room tucked behind the bar—an intimate, tucked-away space perfect for a celebratory dinner. The restaurant’s standout Josper grill locks in flavor and ensures every steak is perfectly juicy, making this one of Sarasota’s top spots for a memorable night out.