Travel Guide to Florida’s Charming Longboat Key

As a longtime Tampa resident, Longboat Key is my go-to Gulf Coast beach destination when I want to feel totally transported. When you drive onto the northern end of this sand-spun island across the Longboat Pass Bridge — with the glittering expanse of the Gulf of Mexico and bobbing boats all around — it feels so much like being in the Florida Keys. And because so much of Longboat Key is residential, the beaches here rarely feel crowded. Wherever you stay, just stroll a bit north or south, and you’ll likely find yourself alone with the shorebirds on the sand.

“Longboat Key is quite residential with a lot of full-time residents. There are not so many public beaches, so it offers a greater aspect of privacy,” says Lauren Mincberg of Tampa, who frequently vacations here with her family at Moku, a Polynesian-inspired, five-bedroom house they operate as a vacation rental on an island off Longboat Key.

“Longboat really feels like families have lived there and been traveling there for generations, so you see all different generations of people gathering together,” Mincberg says.

The biggest news of late on this barrier island just minutes west of downtown Sarasota is the fall 2024 opening of super-luxe St. Regis Resort Longboat Key, positioned roughly mid-island on Longboat Key. Fronting a gorgeous stretch of white sand with incredible amenities like a waterfront tiki bar, the Monkey Bar, it’s already poised to become one of Florida’s most coveted beachfront resorts.

“Longboat Key is just about serenity and natural beauty, and then you have the sophistication of St. Armands Circle and Saraosta right nearby,” says the hotel’s general manager, Winfred van Workum. “The restriction on high rises keeps it very beach-like here. People remark that it’s like the Caribbean or South Pacific.”

Read on for my best tips for visiting Longboat Key.

Best Hotels & Resorts

The St. Regis Longboat Key Resort

Newly opened during the fall of 2024 as Longboat Key’s first major new resort development in over half a century, The St. Regis Longboat Key Resort sprawls across acres fronting the sparkling Gulf of Mexico and ushers in a new era of luxury for visitors to the island. Rooms and suites have a yacht-like appeal, with sweeping Gulf of Mexico views through floor-to-ceiling windows that cast a silvery glow upon everything. On-site amenities include a 500,000-gallon saltwater lagoon where guests can snorkel among (de-barbed) southern stingrays and thousands of tropical fish; a 20,000-square-foot spa complete with a sauna, cold plunge, steam room, and private pool overlooking the beach; a winding river; and separate family and adults-only pools fronting the gulf. The resort’s gorgeous lobby bar quickly became a favorite among sophisticated locals. And on-site restaurants include the excellent Riva for coastal Italian fare, Nikkei-style Oshen (an incredible al fresco perch for sunset and sushi), and CW Prime, where steaks and seafood sizzle on the Josper grill.

Zota Beach Resort

Take a dip in the infinity-edged pool overlooking the Gulf of Mexico, kick back on your waterfront balcony, or settle in with a mai tai and mahi mahi tacos by the pool bar. A beach vacation at the 187-room Zota Beach Resort combines the best of a luxury resort in a modern setting, with rooms and one-bedroom suites (the latter have kitchenettes) decorated with contemporary furnishings and bright artwork. On a balmy Florida night, there’s nothing like sipping from the extensive wine list at Viento Kitchen+Bar, with a Caribbean and Florida-inspired menu and a glass wall of doors that folds open to let the silky breeze inside.

The Resort at Longboat Key Club

If you’d love a beach vacation with the Gulf of Mexico at your doorstep and plenty of tennis and pickleball courts waiting for play, The Resort at Longboat Key Club  is hard to beat for an active escape. Part of Opal Collection, the all-encompassing property sprawls across 410 acres with 226 guest rooms and suites and has two waterfront golf courses, a deep-water marina, a full-service spa, and five restaurants, including the farm-to-table Tavern & Whiskey Bar.

SeaHorse Beach Resort

Located roughly mid-island on Longboat Key, this low-key condo-style property has individually owned units directly on the beach. Choose from studios and one- and two-bedroom accommodations at SeaHorse Beach Resort, all with full kitchens, balconies, or patios overlooking the pool and Gulf of Mexico, barbecue grills, and on-site laundry facilities. The SeaHorse is a favorite for longer stays and travelers looking for an at-home feel, and it’s particularly popular with vacationing families.

Sand Cay Beach Resort

Here’s another great bet for a condo-style stay with units located directly on a beautiful stretch of Gulf of Mexico beachfront. The pool at Sand Cay Beach Resort may not have gulf views, but the beach is not far, and there’s a waterfront communal outdoor barbecue area set just back from the dunes where you can grill up dinner while gazing out at the shimmering water. All of the condos are individually owned and decorated, with full kitchens and balconies or patios for enjoying the views.

Best Things to Do

Set sail on a sunset cruise.

You’ll be picked up about an hour and a half before sunset to sail out with Four Keys Charters on a beautiful on-the-water adventure through Sarasota Bay and the Intracoastal. A complimentary bottle of bubbly will be popped as you scout for dolphins and manatees and wait for the main event — watching the golden orb sink over the Gulf of Mexico and turn the sky delightful shades of pink and orange.

Explore Sarasota.

Thriving and artsy downtown Sarasota is just a few minutes away from Longboat Key. Put a visit to the incredible Ringling museum and its gorgeously landscaped grounds on your itinerary as well as some time spent breathing in the fresh air and views among the banyan and mangrove trees of the Marie Selby Botanical Gardens, which recently expanded with more gardens, a welcome center, and a great little restaurant, The Green Orchid. St. Armands Circle brims with sidewalk cafes and shopping.

Learn about sea turtles.

Seven species of sea turtles — including loggerhead, green, and hawksbill turtles — nest and hatch on the powder-fine sands of Longboat Key from May through October. You may get lucky and see hatchlings making their way toward the water during a morning walk or catch a mother sea turtle lumbering ashore here after dark. On Saturdays in June and July, you can head to the beach during free sea turtle walks after dark with Longboat Key Turtle Watch to learn more about these special animals from the people working to protect them.

Scout for manatees and dolphins during a guided kayaking tour.

Florida’s iconic nature is all around you on Longboat Key, and the best way to experience it upclose is by getting out on the water in a quiet way during guided kayaking tours with Happy Paddler that launch from the island’s scenic shores into Sarasota Bay. Families with younger kids love the Coastal Island Tour, which takes them between Anna Maria Island and Longboat Key where they might see dolphins and manatees. Look out for the elusive green flash when the sun goes below the horizon during sunset paddling tours.

Play some pickleball or shuffleboard at Bayfront Park.

The town of Longboat Key owns this dog-friendly county park on the bay side of the island that’s a favorite off-the-beach spot for catching the sunset. Bayfront Park’s many amenities include dedicated pickleball courts, tennis courts, a playground, and a kayak launch.

Best Restaurants

Whitney’s

Longboat Key and Sarasota locals love this diner for its come-as-you-are atmosphere and frosé all day on Saturday and Sunday, when the brunch crowd arrives by beach cruiser and golf cart for breakfast burritos and biscuits and gravy. Whitney’s cinnamon and sugar ricotta donut holes are a fan favorite, and don’t leave without trying the key lime pie.

Euphemia Haye

With just 28 seats, Euphemia Haye might be Longboat Key’s most romantic reservation for fine dining that feels like a true local secret. Italian shrimp dishes and cannelloni, roasted duckling, and Grecian lamb shank are among the menu favorites. After dinner, small parties (no more than six people) can slip upstairs to the Haye Loft for a drink in the lounge terrace or handmade desserts by the restaurant’s pastry chef in the Dessert Room.

Sips & Gelato

Tucked away in Whitney Plaza on the northern end of Longboat Key, Sips & Gelato does cold-pressed juices and impeccable espresso drinks and gelato. Open early til around 2 p.m., it’s a breakfast and brunch favorite for pastries, smoothies, bagel sandwiches, avocado toast, and more in a setting filled with art and tropical plants.

Shore

Boaters relish arriving by the water at the dockside Shore, just south of Longboat Pass and west of Jewfish Key (but don’t worry — you can get here by land, too).  Shrimp ceviche and guacamole goes down easy with a frosty margarita, and you can never go wrong with something hooked locally, like the pan-seared snapper with citrus butter or miso-marinated black grouper. Most of the tables overlook the water, too.

Dry Dock Waterfront Grill

Another waterfront favorite with plenty of al fresco tables on a dockside patio, Dry Dock Waterfront Grill is beloved among the boat crowd, too. It’s known for great grouper sandwiches, lobster tacos, and a divine key lime pie.  Panoramic views of Sarasota Bay are the cherry on top.

Mar Vista Dockside Restaurant

Tables set on the sand under flowering trees overlooking Sarasota Bay make Mar Vista Dockside Restaurant a top choice whether you’re celebrating a special occasion or looking for something laid-back with a true sense of place. Come for beer-battered hogfish and chips and Southern-inflected fare like the shrimp po boys, crab cake sandwich, or corn and jalapeno hush puppies.

Best Time to Visit

Longboat Key and surrounding areas in Sarasota County are awash in 255 days of sunshine a year, according to the county’s Economic Development Corporation, so it’s easy to spend most of your time outside enjoying all that vitamin D. Winters can get a bit nippy when cool fronts move along the coast, but spring and fall are reliably balmy. Keep in mind that Florida’s hurricane season runs between June 1 and the end of November.

How to Get There

Arriving in Longboat Key is a cinch thanks to the growth of Sarasota-Bradenton International Airport and airlines like American and Allegiant Air adding routes here. You’ll have even more options for landing in these parts when you fly into Tampa International Airport, roughly 58 miles (less than 1.5 hours by car) to the north or St. Pete-Clearwater International Airport, just 50 miles to the north ( roughly one hour away).

How to Get Around

Bikes: Longboat Key is prime for exploring on two wheels, with a car-free bike path running the length of the barrier island with access to beaches and restaurants. Ride & Paddle rents beach cruisers, geared bikes, kids bikes, and bikes with trailers and kiddie seats.

Share rides and public transit: The Breeze Transit network operates bus and trolley routes in Sarasota County and a curb-to-curb rideshare service using minivans and SUVs, Breeze OnDemand, that you can order via the app or a phone call for up to four passengers.