15 Cool Things to See & Do in Siesta Key On Your Florida Vacation

Thinking about exploring Florida’s Gulf Coast? Be sure to carve out time to enjoy the best things to do in Siesta Key. Located in Sarasota County, this popular tourist destination is known for its beautiful beaches, blissful weather, cool local villages, and epic sunsets.

The eight-mile-long island is easy to get around thanks to the island’s impressive Siesta Key Breeze Trolley. Jump from beach to beach without having to turn the ignition. Spend your evenings with locals sipping cocktails with beautiful sea views, or take a road trip to other amazing Sarasota County destinations under an hour away.

Not sure what to do on your vacation? Start planning your trip with this guide to the best places to visit in Siesta Key, FL.

Must-see places to visit

Siesta Key Beach

Most travelers start their Siesta Key vacation roaming along the white sands of Siesta Key Beach. Rated as one of the top beaches in the United States, Siesta Key Beach is packed with popular activities to keep you active throughout your trip.

The pristine beach is joyously soft and effortlessly floats between your toes. From wherever you lay down your beach gear along the shores, you’ll have brilliant views of the blue water and the soft ocean breaks. There’s also a small playground to keep the kids entertained while you work on your tan.

Siesta Key Beach

You could spend all day soaking up the rays and reading a page-turner on Siesta Beach, but it’d be remiss not to make use of the many local water sports on offer. Siesta Key has a glorious breeze that kicks up a notch offshore, making it a perfect spot for parasailing, windsurfing, and kiteboarding.

Better yet, venture further away from the coastline on a boating or fishing adventure, grab an unforgettable view of dolphins splashing around in the wild, or enjoy some adrenaline-pumping jet skiing.

(Of course, if you’d rather just spend the day strolling along the shores, people-watching, and swimming in the clear waters, we wouldn’t blame you!)

Siesta Key Village

Just five minutes north of Siesta Beach is the happening Siesta Village. The village hosts several of the island’s top points of interest. It’s home to a vibrant local community, shopping, and some of the barrier island’s finest dining.

Siesta Key Village is the perfect place to spend some time away from the beach. The town is fun and easy to walk around. It’s home to several highly rated art galleries, boutique stores, and local markets, which provide excellent indoor fun. If you don’t want to be eating out three times a day, the village also has a grocery store to load up on food that’ll work perfectly for BBQ meals at the beach’s picnic areas.

If you happen to be around on a Sunday morning, pop into the Siesta Farmers Market. Load up on produce, artwork, crafts, jewelry, and even rum from Florida’s oldest distillery.

But the village really comes to life after the sun goes down. Siesta Key Village offers the island’s best nightlife, as locals and tourists combine to create an exciting atmosphere. Head to Daiquiri Deck for outside drinks and live music.

Crescent Beach

Siesta Key Beach may hog all the glory, but there’s no doubt that Crescent Beach is one of the most beautiful places to see on the barrier island. The sparkling turquoise waters will immediately catch your eye before you begin to wonder: “Why is the beach is so quiet?”

Freat Blue Heron on the Crescent Beach

Although it’s on the most beautiful beaches on Siesta Key, Crescent Beach sees a smaller crowd as it’s more secluded than its famous sibling. Midnight Pass Road provides “blink-and-you’ll-miss-it” public beach access. Another reason the crowds are sparse is the lack of amenities. However, it’s an easy workaround.

The end result is sparkling waters to swim in, with plenty of space to spread out of the powder-like sand. At the southern end of the beach is another Siesta Key highlight: the Point of Rocks.

Point of Rocks

Wondering where to go in Siesta Key for snorkeling and diving? Look no further than the Point of Rocks. The aptly described point isn’t as scary as it sounds; Point of Rocks also happens to provide fun for the entire family.

At Point of Rocks, the water’s depth doesn’t reach over five feet, making it welcoming for families with kids of all ages. The sprawling tide pools provide glimpses of vast marine life. Spot fish zipping between enclaves or crabs crawling along the surface.

In order to get to the Point of Rocks, first, arrive at Crescent Beach and stroll until you reach the southern point. A large wall, eroded over thousands of years by the Gulf of Mexico, greets you. Beyond the wall is a magnificent display of natural pools and diving areas. Just be sure to wear something protective on your feet to explore the Point of Rocks to the fullest extent.

Turtle Beach

Like Crescent Beach, another way to beat the crowds is to venture down to Turtle Beach. Even at the height of tourist season, the beaches on the southern end of the island don’t get nearly as crowded. This may be why Turtle Beach is much-loved among locals.

The quartz sand at Turtle Beach may not be as soft as the legendary Siesta Key Beach, but the stark drop-off towards the ocean creates a magnificent spot to sit. From there, take just a couple of steps into the water for a refreshing dip.

Turtle Beach

Turtle Beach comes with several amenities to make your day on the sand even better, including a parking lot and a boat ramp for sunset sailing or launching your kayaks.

Right behind the beach is a spacious park for the young ones to run amok. In the park, you’ll also find a pavilion plus plenty of park benches for an afternoon picnic experience, along with restrooms and showers.

If you’re up for some family activities, make use of the horseshoe pits and beach volleyball nets. Turtle Beach is also one of the top shelling beaches in the area. Dig through the sand to find a couple pretty seashells to bring back home as a souvenir!

Don’t want your beach experience to end? Stay under the stars with the ocean breeze nipping at your tent at the Turtle Beach Campground, one of the rare beach campsites in Florida.

Siesta Key Breeze Trolley

Tourist islands aren’t renowned for great public transportation, but that’s simply not the case here. The impressive Siesta Key Breeze Trolley is the key (pun intended!) to exploring Siesta Key in one day. The best part about it? It’s free!

The Breeze Trolley operates from 10 am to 10 pm every day of the week, except Friday and Saturday, when the trolley runs until midnight. The colorful trolley on wheels begins in Siesta Village and makes its way down to Turtle Beach at the southern tip of the island. The two main roads the trolley drives along are Beach Road and Midnight Pass Road, allowing you to avoid needing to search for parking spots.

Now that you’re rushing out to cancel your rental car, click here to see a map of the route.

Sunset Point

Nothing beats facing west and watching the sunset on the water. So, it’s no surprise that one of the essential things to do in Siesta Key is to grab a front-row seat for a dazzling display by visiting the appropriately named Sunset Point. Although half of the island faces west, Sunset Point is a popular gathering place, where excited crowds mark the end of another sun-filled day.

Sunset Point sits at the northern end of Siesta Beach. If you’re hanging out on the sands, walk to the point and set up your beach chairs before the rest of the island community arrives. Sit back with a cold beverage and see if you can spot the famous “green flash.”

You can swim at Sunset Point during the day, but keep in mind that there are no lifeguards on that part of the beach.

Siesta Key Drum Circle

Beyond pristine coasts and epic sunsets, Siesta Key has ample local culture and fun events. One of the coolest things to see on the island is the Siesta Key Drum Circle. The iconic local tradition combines dancers, artists, and families from around the island and region in an event of music and camaraderie.

Siesta Key Drum Circle

If you’re in town on a Sunday evening, be sure to make your way to Siesta Beach an hour before the sun goes down. 52 times a year, large crowds gather on the beach for this fun-filled activity. The drumming begins first with a siren and then with the pitter-patter of the instruments.

As the music soars into the sky, the community sings in unison, bringing together young and old. Random instruments are handed out among the revelers, with the opportunity for everyone to take part in the event.

Siesta Key Watersports

Add some adrenaline-pumping water activities to your itinerary by booking an excursion with Siesta Key Watersports. The popular outfitter offers an array of fun and action-packed tours and activities around Siesta Key, all focused on exploring its crystal-clear waters.

Rent a jet-ski to ride the Gulf waves at full speed or see Siesta Key from above on a high-flyin’ parasailing tour. If you’d prefer a quieter day (or evening) on the water, Siesta Key Watersports also offers dolphin cruises and sunset cruises. 

Siesta Key Oyster Bar

Let the island party vibes overtake you with a meal and drinks at the Siesta Key Oyster Bar. Located steps from the beach, this restaurant & bar, nicknamed “SKOB” by locals, is one of the most popular places to eat & drink on the barrier island.

Siesta Key Oyster Bar

As the name implies, oysters are the bar’s mainstay food. Get in on the action during Big G’s Oyster Happy Hour (3 pm to 6 pm daily) to save 50% on a dozen oysters.

Is seafood not your thing? There are plenty of other snacks on the menu, too, from their award-winning wings to the Big Boy Mac N Cheese. (Of course, you could always just settle for sipping on their wide range of tropical cocktails, too!)

Beer Can Island

On the northern end of Longboat Key, Beer Can Island is one of the must-see places to go in Siesta Key. Roughly 45 minutes north of Siesta Key Village, Beer Can Island is full of sprawling mangrove forests with a white sand beach cutting in. The natural environment is both stunning and fragile, with bleached driftwood finding forever homes on the picturesque local beach.

Beer Can Island Beach

A scene straight out of Cast Away, Beer Can Island is also full of color and visual contrasts. The turquoise colors collide with the forests while the fallen trees feel perfectly out of place in such a fairytale-like environment. Be sure to bring your hammock to squeeze the most out of this popular attraction.

The majority of visitors come to the island by boat, making use of the shallow waters to beach their boats without needing a dock. Or you can reach Beer Can Island on four wheels via Broadway Street or North Shore Road.

Anna Maria Island

For anyone who loves a good road trip, then Anna Maria Island, an hour north of Siesta Key, has answered your prayers. A day trip to Anna Maria Island will provide travelers with a unique coastal community with a storied past and plenty of tourist attractions.

Anna Maria Island

There’s so much to do on Anna Maria Island that you’ll be hard-pressed to do it all in a single day. One of the top activities is visiting Bean Point. With its white sandy beaches, untouched nature, and calm blue waters, it’s easy to see why locals love to come here. If you have time, return to Bean Point in the evening for a magical sunset.

Another beach to add to your road trip itinerary is Bradenton Beach. Come here for some more sun, restaurants, and galleries, plus the Historic Bridge Street Pier.

Sarasota

Being the gateway town to Siesta Key, you’ll likely pass through Sarasota to begin and end your travels. But the town doesn’t have to be just a waymarker. In fact, the beautiful city of Sarasota is well worth exploring in its own right.

Sarasota

For a splash of urban life and culture, cross Sarasota Bay for a great and quick escape from Siesta Key. Among the top Sarasota tourist attractions are gorgeous gardens, nightlife, and restaurants. There are also several top-notch museums to explore, none better than The Ringling. The impressive art museum opened in 1927 and today comprises over 10,000 pieces of art, photos, and sculptures covering numerous eras.

Another popular local attraction is Sarasota Jungle Gardens. The gardens combine the beauty of a botanical setting with many exotic animals, from pink flamingos to alligators.

Venice Beach

Thirty minutes south of Siesta Key is the town of Venice. Named for resembling the famous Italian city, Venice’s most popular beach is, of course, Venice Beach. Just a brief walk away from the city’s historic downtown, the beach offers balmy waters and superb city views.

Venice Beach

Like many of the finest beaches along Florida’s Gulf Coast, Venice Beach presents guests with sparkling white sand, calm waters, and Instagrammable lifeguard watchtowers. The enormous beach also comes with waterfront restaurants and bars, which add a fun layer of atmosphere to Venice Beach.

When you’ve had your fix of sun, you don’t have to be in a rush to return to Siesta Key. Within walking distance are several historic buildings featuring architecture influenced by the Renaissance. Dotting the streets of Venice, FL, you’ll also find fun shops, parlors, cafes, and bars.

Lido Key

Just north of Siesta Key is another key that perfectly balances man-made fun and untouched tranquility. Lido Key is a quiet stretch of white sand compared to Siesta Key, Anna Maria Island, and Venice. (Not that the locals are complaining!)

Lido Key

Lido Key is home to an expansive mangrove forest. Discover the exciting ecosystem by exploring the many natural mangrove tunnels on a kayak or a stand-up paddleboard (SUP). While kayaking along the waterways, keep your eyes peeled for wildlife, including a variety of species of birds and, if you’re really lucky, manatees!

The peaceful Lido Beach offers a welcoming escape and is a popular spot to surf along the local coast. (Not to mention, the beach gives you front-row tickets to yet another spectacular sunset; it’s an especially romantic spot for couples!)

Beyond the sand, there’s plenty to see and do around Lido Key. Relax under the shade in South Lido County Park. Fire up the grill and watch the hoard of boats roll on by. Later, before returning to Siesta Key, stop by St. Armand Circle for ice cream at Kilwin’s.

Recommended places to stay

No matter what you’re looking for, there’s a wide variety of accommodation options throughout the barrier island, from vacation rentals to hotels to resorts. Here are a few ideas…

Captiva Beach Resort

Captiva Beach Resort

Although it offers only 19 rooms, Captiva Beach Resort is a fantastic choice for guests wanting private beach access. All the rooms are equipped with full kitchens for a complete self-catering stay. Located steps from Crescent Beach, amenities include barbecue facilities, shuffleboard, and free WiFi.

The Capri at Siesta

The Capri at Siesta

One of the island’s top-rated hotels, The Capri at Siesta sits in an excellent location on Turtle Beach, close to restaurants, boutique shops, and entertainment options. Dazzle in lovely views of Siesta Beach from the palm-shaded courtyard. The hotel offers affordable lodgings at weekly and daily rates.

Twin Palms at Siesta

Twin Palms at Siesta

Steps away from Siesta Beach, Twin Palms at Siesta offers spacious rooms with full kitchenettes, flat-screen TVs, and large premium beds. Sit on your private balcony to swoon over amazing sunset views over the turquoise waters. Other amenities at this hotel include a heated outdoor pool.

Tropical Breeze Resort

Tropical Breeze Resort

For a luxurious stay with family and friends, look no further than this beautiful beachside hotel. The resort offers everything from studios to three-bedroom suites. Within walking distance, you’ll find several beach restaurants and shopping boutiques. For a self-catering stay, take advantage of the resort’s free grocery delivery. You’ll also enjoy free 2-hour bike rentals for exploring more of the island.

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15 Fun & Cool Things to Do in Siesta On Your Florida Vacation

Treksplorer

Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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