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Siesta Key is a charming barrier island on the southwest Gulf Coast of Florida, renowned for its beautiful beaches, fun nightlife, and exceptional sunset views. The area is packed with hotels and vacation rentals, and it quickly gets busy during peak season, with many visitors keen to lounge on the white sand beaches and swim in the turquoise waters.
Despite being one of the most popular Florida beach towns, Siesta Key offers far more than just sunbathing. If you’re wondering what this sunny region of the country has to offer, check out this travel guide to help you plan an itinerary for your upcoming Siesta Key vacation.
1. Try New Watersports on Siesta Key Beach
Siesta Key Beach is one of the best beaches in the USA for families, thanks to its soft white sands and relatively calm waters. It’s a great place to try new watersports because there are plenty of rental shops offering equipment hire, lessons, and tours.
Adrenaline junkies will love jet skiing or parasailing, but those who prefer a quieter pace may be better suited to kayaking or stand-up paddleboarding. Lifeguards are positioned along Siesta Beach every day of the week so you can head out into the water with peace of mind.
2. Ride the Siesta Key Breeze Trolley
The Siesta Key Breeze Trolley operates seven days a week to help locals and tourists get around without having to drive and worry about parking.
It runs from Siesta Key Village to Turtle Beach and back every 10 to 30 minutes, with stops dotted along Ocean Boulevard, Beach Road, and Midnight Pass Road. The trolley is free to ride, and you can hop on and off at whatever stop suits you along the way.
3. Drink and Dine in Siesta Key Village
Siesta Key Village is a town square lined with restaurants, bars, gift shops, and art galleries. It’s the hub of Siesta Key’s nightlife and it has a fantastic atmosphere throughout the afternoon and into the night.
The eateries are all fairly relaxed, but they serve delicious local dishes, particularly those that specialize in seafood, such as Siesta Key Oyster Bar and The Lobster Pot. Siesta Village can get very busy during peak season, so be prepared to wait in line to get a table.
4. Go Snorkeling at Crescent Beach
Crescent Beach lies just south of Siesta Beach, and it tends to be a little quieter due to its limited beach access points. It’s home to Point of Rocks, a popular snorkeling spot that is ideal for total beginners. The waters are calm, clear, and no deeper than around 20 feet, so you can see an incredible array of colorful coral, tropical fish, and crustaceans.
5. Dance at Siesta Key Drum Circle
Sunsets are spectacular when watched from Siesta Key’s beaches — so much so that they’re celebrated by locals every Sunday in the form of a Drum Circle.
Drummers congregate around an hour before sunset near the concession stand on Beach Road, and crowds vary in size week to week, with the biggest gatherings usually taking place in the summer. You might even be lucky enough to see dancers, hula-hoopers, firebreathers, and various other talented performers.
The community atmosphere never fails to be magical, so bring a beach chair or towel and settle in for a beautiful experience.
6. Search for Shells and Shark Teeth on Turtle Beach
With most tourists flocking to Siesta Beach and Crescent Beach, Turtle Beach is considered something of a hidden gem. It lies at the southern end of the island, which is a little less developed than the northern end.
There’s a covered pavilion, picnic tables, a playground, volleyball courts, and a horseshoe pit, making it the perfect beach for families. The sands here are coarser than on Siesta Key’s other public beaches, but they’re excellent for finding shells and shark teeth. Take a colander to sift the sand and see what treasures you can find.
7. Listen to Live Music Over Dinner or Drinks
One of the best things about Siesta Key’s laid-back nightlife is that it’s easy to catch live music while you’re having dinner or a few drinks. There are plenty of bars and restaurants that host local and national musicians and DJs. Gilligan’s Island Bar and Grill is a tiki-style bar that hosts live bands on their front deck every day.
Daiquiri Deck keeps Siesta Keys’ pub crawl scene alive and hosts a DJ every weekend to get patrons dancing as they sip cocktails. Captain Curt’s Crab and Oyster Bar serves delicious fresh seafood and hosts local musicians regularly.
Hub Baja Grill is known for its tasty Latin American and tropical seafood dishes, with live music throughout the day and night. Finally, The Beach Club is a popular happy hour joint that regularly hosts live music events.
8. Eat Fresh, Local Fare at Siesta Key Farmers Market
The Farmers Market takes place in Siesta Village every Sunday between 8 am and 12 pm, and it’s a fantastic place to pick up delicious local produce and tasty hot food. There’s a great mix of vendors, so it’s easy to find dishes that suit a variety of tastes. You’ll also find clothing, flowers, artisanal spirits, and much more.
9. Visit Anna Maria Island’s Pretty Beach Town
Anna Maria Island is a pretty barrier island that lies north of Siesta Key and just south of Tampa. It’s a scenic hour-long drive to reach it, and there’s plenty to see when you get there. The beach town of Anna Maria is home to attractive historic buildings, lovely beaches, and plenty of bars and restaurants.
The area surrounding the town is fairly wild and there are some excellent hiking trails to explore here. Be sure to stop off in the city of Bradenton along the way, where there are several interesting sights, such as the Bishop Museum of Science and Nature, where you have the chance to see rescued manatees in rehabilitation.
10. Shop for Souvenirs at St. Armands Circle
St. Armands Circle is a unique shopping destination with a circular green space at its heart. There’s a fantastic range of chain and independent stores here selling clothing, art, homewares, jewelry, and more. Plus, there are restaurants, coffee shops, and even spas and salons, so you can spend an entire day pampering yourself.
11. Eat Frozen Treats at Siesta Key’s Ice Cream Shops
A beach vacation wouldn’t be complete without ice cream, and Siesta Key is home to plenty of fantastic creameries and gelato shops. Big Olaf Creamery has been a popular spot since it opened in 1982. It serves delicious ice cream handmade by Amish craftspeople.
For authentic gelato, swing by Made In Rome, which produces small, fresh batches every day using the finest organic ingredients.
If you want ice cream with a difference, head to Sub Zero, where liquid nitrogen is used to instantly freeze ice cream to ensure an ultra-smooth and creamy product.
Looking for a more traditional take? Visit Abel’s, where you can enjoy classic ice cream sundaes, floats, and milkshakes.
12. Catch a Show at The Circus Arts Conservatory
Sarasota was the winter home of the renowned Ringling Brothers back in the 1920s and 30s, and the circus has been an important part of the city’s history ever since. Head into Downtown Sarasota to watch a performance at the Circus Arts Conservatory. Shows take place across three venues — a traditional European-style Big Top, a historic theater, and a new Sailor Circus Arena.
13. See Great Art and Architecture at the Ringling Museum
The Ringling Museum is an impressive collection of art and antiquities that was originally created by John Ringling and his wife, Mabel, in the 1920s.
Today, The Ringling is comprised of multiple buildings, including the original museum, several new galleries, and the Ca’ d’Zan—a Venitian revival mansion that was once the Ringlings’ private residence. The museum offers an excellent variety of artworks, from classic to contemporary, including one of the best collections of Asian art in the US.
14. Meet the Marine Life of Florida at Mote Aquarium
Mote Marine Aquarium is one of the best in southwest Florida, thanks to its wide variety of species and interactive elements. You can expect to see manatees, sharks, otters, turtles, jellyfish, and many more fascinating critters. There’s also an interactive boat tour on offer where you can meet the likes of sea horses, puffer fish, and stone crabs.
15. Tour Siesta Key and Sarasota on an Electric Bike
Cycling is a popular mode of travel in Siesta Key with many hotels and resorts offering free bike rentals to help their guests get around. A fun way to get the lay of the land when you first arrive is to join an Electric Bike Sunset Tour, during which a local guide will show you the city’s main sights and highlight the best vantage points from which to watch the sunset.
16. Take a Boat Tour or Fishing Charter in the Gulf of Mexico
For a totally different view of Siesta Key, head out into the Gulf of Mexico and admire the coastline. If you’re a keen angler, you can head out on a fishing charter to see what you can catch. If you’d prefer to relax and take in the views, join a boat tour and look out for dolphins or climb aboard a sunset cruise for a romantic evening on the water.
17. Have a Round of Golf on Longboat Key
Longboat Key lies just north of Siesta Key and it’s known for its luxury hotels and resorts. There are two fantastic golf courses on the island — Harbourside and Links on Longboat, both of which offer challenging play with beautiful waterside views.
You can expect to see the likes of bald eagles, ospreys, herons, swans, pelicans, and rare pink spoonbills as you play. There are also excellent facilities at the clubhouse, including a spa with steam rooms.
18. Spot Wildlife at Florida’s State Parks
If you love exploring the great outdoors, be sure to spend at least a day of your trip at one of the state parks that lie close to Siesta Key. You can go hiking or take canoe or kayak tours through mangroves to look out for native wildlife such as manatees, otters, and alligators. Popular parks include:
- Neville Wildlife Preserve at Little Sarasota Bay
- Robinson Nature Preserve in Bradenton
- Myakka River State Park in Sarasota
- Oscar Scherer State Park in Osprey
- Ted Sperling Park at South Lido Key Beach
What Will You Get Up To In Siesta Key?
There’s no shortage of fun things to do in Siesta Key and the surrounding Sarasota County area. Which of these fun activities will you try on your upcoming getaway?
