Siesta Key, Florida, Has Some of the Best Beaches in the State — Plus Frequent Dolphin Sightings

With eight miles of quartz-laden, sugar-soft sand, frequent dolphin sightings, and calm Gulf waters, Siesta Key, just off the southwestern coast of Florida, has all the ingredients for a relaxing beach vacation. But there’s lots of adventure around the bucolic island, too, from deep-sea fishing and snorkeling to paddling and fishing. And that’s to say nothing of the fact that it’s just 10 minutes from the museums, restaurants, botanical gardens, and attractions in Sarasota, one of the best places to retire in the U.S.

Once called Little Sarasota Island, Clam Island, and Sarasota Key, Siesta Key was renamed in 1907, just a year after the first hotel opened on the island. Kelly Defebo, vice president of marketing and communications at Visit Sarasota County, grew up along the Gulf Coast and cites Siesta Key as her go-to spot whenever she needs to recharge and reconnect. “Siesta Key has the ultimate laid-back beach vibe. Sunsets anywhere are gorgeous, but they are not to be missed here. Locals bring their drums and people dance and celebrate as the sun goes down. I feel like I’m on vacation without being far from home,” she says.

We also tapped Kristen Green Seymour, a writer who lives just a few miles from Siesta Beach in Sarasota, to find out what’s so special about Siesta Key. She says, “You can walk from end to end on miles of white sand so fine, it feels like sugar, and if you keep your eyes peeled, you’re likely to spot dolphins just a bit offshore. The sky explodes in pinks, purples, oranges, and reds in the 30 minutes following the official sunset. And while Siesta Key Village is busy and has lots to offer, it also still feels relatively small and local compared to many other beach towns.”

Best Hotels and Resorts

Vacation Rentals

According to both of our local experts, vacation rentals represent the bulk of good accommodations on Siesta Key. Defebo likes Prime Vacations for multigenerational family get-togethers, group celebrations, and reunions. Units range from two to eight bedrooms with fully equipped kitchens. “[The company] has spectacular three-story homes with a rooftop deck, a pool, and all the amenities. If you didn’t want to leave the house, you wouldn’t have to,” Defebo says.

In addition to several homes, Prime Vacations also represents the hotel where both Defebo and Seymour send out-of-town guests, Tropical Breeze Resort. Seymour stayed here on vacations before becoming a permanent resident, noting that “it allows pets, is right by the beach, and has a tremendous variety of room options.” Defebo also loves the different accommodation styles: “It has everything from efficiencies to three-bedroom suites adjacent to Siesta Key Village. You can pick where you want to go and what suits you. You get the benefit of staying within a resort, but because of the way it’s set up, you get to feel like you’re living like a local, too,” she shares. Amenities at the resort include two pools, a spa, grilling areas, and family games and event programming. The property also partners with several local companies to facilitate kayak tours, boat rentals, and more.

Best Things to Do

Snorkel Point of Rocks.

Located on the southern end of Crescent Beach, the warm, shallow, and crystal-clear waters surrounding Siesta Key’s Point of Rocks provide the perfect environment for snorkeling. Both casual and seasoned snorkelers can observe snook, snapper, sheepshead, nurse sharks, red sponges, and more marine life. If you’re lucky, you may even spot a pod of dolphins frolicking or a manatee meandering while exploring the pristine environment.

Spend the day on the beach.

Defebo and Seymour agree the beach is the main attraction on Siesta Key, and Siesta Beach is one of the best in Florida, with an array of shells, calm waters, and soft sand. Turtle Beach and Crescent Beach are two other solid options, both with sand made of 99 percent ground quartz that never gets hot on your feet no matter the temperature. Defebo appreciates the accessibility of the beach, too, noting the Mobi-mat® ADA pathway that runs straight out to the water’s edge on top of the sand at Siesta Beach’s West Concession area.

Go fishing.

The Gulf of Mexico is known for its abundant fish, and on Siesta Key, Defebo loves CB’s Saltwater Outfitters for boat rentals and charter fishing expeditions where you can catch giant tarpon, bonito, cobia, tripletail, jack crevalle, kingfish, Spanish mackerel, and more. She says, “The crew is knowledgeable, and they have a great shop where you can get any supplies you need to fish off the beach if you don’t want to go out on a boat.” They also offer sunset cruises, parasailing, and golf cart rentals.

Kayak or enjoy stand-up paddleboarding at Turtle Beach.

Seymour considers kayaking or stand-up paddleboarding out on Turtle Beach, on the south end of Siesta Key, an absolute must. She says, “Depending on the time of year, you might encounter manatees, dolphins, ospreys, rays, and more. When you rent your vessel, ask for directions to Midnight Pass, which is only accessible by water. When you beach your board and walk over the dunes to see the Gulf stretching out before you, you won’t be worried about the paddle home because you’ll just want to have your mail forwarded. Bring yourself a snack and a drink and stay a while. It’s magic.” Turtle Beach also has a campground for those wanting to spend the night on the sand. Siesta Sports Rentals offers kayak tours, as well as delivers and picks up rentals at Turtle Beach.

Join the Siesta Key Drum Circle.

When Defebo and Seymour have out-of-town guests, the Siesta Key Drum Circle is a must-do. Every Sunday evening, artists, dancers, locals, and tourists gather on Siesta Beach an hour before sunset. Seymour advises, “Parking is at a premium, especially during high season (loosely, Christmas to Easter), so consider taking bikes or the trolley down. Whether you just watch or get in the center with a hula hoop is up to you.” 

Best Shopping 

Siesta Key Village

According to Defebo, Siesta Key Village is the main shopping hub on the island. “It’s a fantastic place to wander around for souvenirs. [Expect] high-end boutiques, beach shops, jewelry stores, and more,” she says. There’s an apothecary, a sandal shop, consignment stores, spots to get T-shirts and swimsuits … practical stops like a drug store and a post office, restaurants, bars, and live music, all within a mile of the Siesta Beach. Every Sunday from 9 a.m. until 2 p.m., the Siesta Key Farmers Market pops up in Siesta Key Village. Shoppers will find fresh produce, original oil paintings, clothing, and handmade crafts.

South Village

If you’re staying at the other end of the island, South Village has everything from beachwear and gifts to groceries and convenience store items. Located at the corner of Stickney Point and Midnight Pass roads in the Crescent Beach area, South Village is home to clothing boutiques, souvenir shops, a post office, and plenty of fishing gear.

Best Nightlife

The Beach Club

If you’re hankering for some live music, a DJ, and a large dance floor, Seymour recommends The Beach Club, where the nightlife thrums Monday through Sunday from noon until 2 a.m. Check out the daily happy hour, which runs from opening time until 7 p.m., while enjoying two bars and a drink cart with stunning beach views.

Daiquiri Deck

Tucked into Siesta Key Village, the Daiquiri Deck was established in ’90s by a young lifeguard born and raised on Siesta Key. A line of daiquiri machines, bright orange and green decor, and open-air seating set the scene here. In addition to the extensive daiquiri list, the location has a menu filled with seafood options like the piña colada-glazed mahi sandwich and gator bites with orange habanero remoulade. It’s open every day from 10 a.m. until midnight. Defebo says to order The Best One — the bartender’s choice option — for a delicious surprise.

Captain Curt’s Crab & Oyster Bar

Captain Curt’s is the longest-running karaoke bar on Siesta Key, established in 1979. Defebo loves this spot for late-night Saturday karaoke soirees with friends. The venue also has live music every afternoon and evening, and unlike other options, it’s located outside of Siesta Key Village.

Siesta Key Oyster Bar

Siesta Key Oyster Bar, or SKOB as the locals call it, is an institution dedicated to a love of the Chicago Bears. It stays open Sunday through Thursday until 11 p.m., and Friday and Saturday until midnight. The patio remains packed and the legendary oyster happy hour runs from 3 p.m. until 6 p.m. daily. The real draw, though, is the scene at night. “It’s a great place to hear live music, and every inch of the walls is covered with dollar bills,” Defebo says.

Best Restaurants

Summer House

For a splurge-worthy dinner, Seymour beelines to Summer House. Open seven days a week from 4 p.m. until 10 p.m., the upscale restaurant serves hand-cut steaks seasoned and grilled to perfection, along with fresh seafood. The 1,000-gallon fish tank in the dining room is an attraction unto itself — it took 1,100 hours to build and was designed exclusively for the restaurant.  

The Cottage

Located next door to the Summer House, The Cottage is another favorite for Seymour. “I recommend getting a spot out back on a weekend evening to catch some live music in an intimate, plant-filled setting,” she says. It’s open seven days a week for lunch and dinner in the heart of Siesta Key Village.

Sun Garden Cafe

According to Seymour, Sun Garden Cafe has the best breakfast in town. She loves the charming, mostly shaded outdoor patio, large portions that often turn into delicious leftovers, and refreshing mimosas. She adds, “The hardest part about coming here is deciding whether to go with a sweet pancake, a baked good, or a savory egg dish.” Breakfast is served all day and you can bring your dog to this pet-friendly hot spot.

Cafe Gabbiano

Defebo touts Cafe Gabbiano as one of the best places for homey Italian food in the area. She says, “They make their pasta by hand. I love the cheese ravioli, but they also have truffle, osso buco, and lobster ravioli, and you can’t go wrong with any of them.” The 4,000-square-foot restaurant is open daily from 5 p.m. until 10 p.m. and offers private dining, as well as outdoor seating on the climate-controlled patio.

Old Salty Dog

After a day at the beach, hit Old Salty Dog, a pet-friendly, British pub-inspired spot that has been going strong since 1985. Order a frozen cocktail and a Salty Dog — a tempura-battered, foot-long hot dog with fries. The latter is topped with sauerkraut, bacon, grilled onions and mushrooms, and American, cheddar, pepper jack, and Swiss cheeses. It’s open seven days a week from 11 p.m. until 9 p.m., with plenty of outdoor seating under the palapa.

Best Time To Visit

Locals know the fall and winter tend to be the best times to visit Siesta Key for temperate weather, smaller crowds, and lower humidity. Defebo agrees, adding that November is her favorite time to have guests. “The Siesta Key Crystal Classic is a sand-sculpting competition held annually in November. It has a theme every year and sand sculptors from around the world travel here to build amazing castles and sculptures from our gorgeous quartz sand,” she says. 

Keep in mind hurricane season runs from June through November, with most storms occurring in August and September, when the waters are warm. This also means you may be able to get a good deal on flights or accommodations during this window.

Related: 10 Best Islands in Florida for Beautiful Beaches, Laid-back Vibes, and Charming Small Towns

How to Get There

Just over the bridge, a speedy 10 miles from Siesta Key, sits Sarasota Bradenton International Airport. With more than 55 nonstop destinations on all major U.S. air carriers, it’s easy to get to Sarasota. Tampa International Airport is also just an hour away from Siesta Key, providing even more options for economical flights. Both airports have Uber and Lyft services or the option of hiring a private shuttle to get to Siesta Key, but Defabo says renting a car is a good choice so you can explore beyond Siesta Key.

For those within driving distance, access could not be easier; Interstate 75 has two exits for Siesta Key — 205 and 207 — that take you in a straight line down to the island.

Areas to Visit

Sarasota

A hub on Florida’s Cultural Coast, Sarasota is just a bridge away from Siesta Key and worthy of some exploration. Defabo says, “Once you go over the bridge, you’re near the quaint Hillview area with shopping and restaurants. Next to that is Marie Selby Botanical Gardens, which has more than 20,000 exotic plants from around the world. After you get to downtown Sarasota, you can park and hop on the trolley that stops at multiple points on Main Street, including the Ringling Bridge onto St. Armands Circle, an eat, play, live community designed by John Ringling for his wife, Mable.” While there, check out The Ringling, a 66-acre estate that houses museums, gardens, and attractions. 

 How to Get Around

Once on Siesta Key, getting around from place to place doesn’t require a rental car (though if you do elect to get one, parking is free on the island). “It’s only 3.5 square miles. Because of the compact size, it’s pretty easy to get around. Whether you’re going to the beach or the store, just hop on a bicycle, scooter, or golf cart,” Defebo says.

Adding to the ease of island transport is the complimentary Siesta Key Breeze trolley. It operates seven days a week, from 8 a.m. until 10 p.m. And if you want to get off the key and hit some of the attractions on the mainland, Breeze OnDemand offers service from tip to tip of Siesta Key. It operates daily for $2 per person, per trip. The best part? You can request a pickup and drop-off at any Siesta Key address and never have to worry about parking a rental car.