Whenever we’re exploring Florida’s Gulf Coast, we try to slot in some time in Siesta Key. Located in Sarasota County, this popular tourist destination is loaded with its beautiful beaches, blissful weather, cool local villages, and epic sunsets. So, it’s no surprise that we always find plenty of fun things to do in Siesta Key whenever we pass through the area.
We love how easy this eight-mile-long island is to get around, thanks to the Siesta Key Breeze Trolley. On our road trips, we often park the car and jump from beach to beach on this convenient route.
Besides hanging out on the beautiful beaches, we also cherish the chance to spend our evenings sipping cocktails with locals to beautiful sea views, or taking road trips to all the other amazing Sarasota County destinations under an hour away.
Ready to plan your vacation to this beautiful barrier island? Let us help you figure out what to see & do with this complete guide to our favorite places to visit in Siesta Key, including our recommended beaches, restaurants, bars, and day trips…
Our tips for what to see & do in Siesta Key
Siesta Key Beach
We don’t think there’s a better way to start your vacation than 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.
When we first visited this pristine beach, we couldn’t get enough of the joyously soft sand that effortlessly floats between the toes. Wherever we laid down our beach gear along the shores, we marveled at the brilliant views of the blue water and the soft ocean breaks. There’s even a small playground to keep the kids entertained while you work on your tan.
We could easily spend all day soaking up the rays and reading a page-turner on Siesta Beach, but we’d be remiss not to recommend the many local water sports on offer. Siesta Key has a glorious breeze that kicks up a notch offshore. We saw plenty of locals and tourists hitting the waves here for a little parasailing, windsurfing, and kiteboarding.
Better yet, we suggest venturing further away from the coastline to go 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, either!)
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 and is home to a vibrant local community, shopping, and some of the finest dining we found on the barrier island.
After a day on the sand, we think Siesta Key Village is the perfect place to spend some time away from the beach. The town is fun and easy to walk around.
Siesta Key Village is 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, we recommend popping into the Siesta Farmers Market. Load up on produce, artwork, crafts, jewelry, and even rum from Florida’s oldest distillery.
But in our experience, 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 (5250 Ocean Blvd) for al fresco drinks and live music. Of course, we loved the frozen daiquiris here, especially when we caught the happy hours between 3 pm and 7 pm. The food menu was surprisingly good, too, though, with Florida-inspired appetizers like gator bites, coconut shrimp, and conch fritters taking center stage.
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 immediately caught our eye and had us wondering: “Why is this beach so quiet?”
Although we think it’s one of the most beautiful beaches on Siesta Key, Crescent Beach sees a smaller crowd as it’s more secluded than its famous sibling. When we first drove down Midnight Pass Road, we noticed this is a “blink-and-you’ll-miss-it” public beach access.
Another reason the crowds are sparse is the lack of amenities. However, we think it’s an easy workaround with a little pre-planning.
The end result is sparkling waters to swim in, with plenty of space to spread out on the powder-like sand. At the southern end of Crescent 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. On our visit, we loved gazing into the sprawling tide pools to catch glimpses of the marine life. Spot fish zipping between enclaves or crabs crawling along the surface.
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, will greet you.
Beyond the wall is a magnificent display of natural pools and diving areas. One suggestion: We would recommend wearing something protective on your feet to explore the Point of Rocks to the fullest extent.
Turtle Beach
Like Crescent Beach, another way we found 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 seems to be much-loved among locals.)
While we didn’t find the quartz sand at Turtle Beach as soft as the legendary Siesta Key Beach, 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.
On our visit, we found several amenities at Turtle Beach to make the day on the sand even better, including a parking lot and a boat ramp for sunset sailing or launching kayaks.
Right behind the beach is a spacious park for the young ones to run amok. In the park, we also spotted 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. We were told by locals that Turtle Beach is also one of the top shelling beaches in the area. Dig through the sand to find 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
After traveling to over 50 countries, we feel fairly confident in saying that 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. And our favorite part about it? It’s free!
The Breeze Trolley (Route 77 Siesta Islander) 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. (And in our experience, that isn’t always easy at the more popular seaside spots!)
Now that you’re rushing out to cancel your rental car, click here to see a map of the route.
Sunset Point
No matter where we are around the globe, nothing beats facing west and watching the sunset on the water. So, it’s no surprise that one of our favorite 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 early 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 we should warn you that there are no lifeguards on that part of the beach.
Siesta Key Drum Circle
Beyond pristine coasts and epic sunsets, we discovered ample local culture and fun events on our visits to Siesta Key. 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.
If you’re in town on a Sunday evening, we recommend making 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 at the Siesta Key Drum Circle, 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.
(We were a little self-conscious at first, but once we “got in the groove,” it was a whole lotta relaxed fun!)
Siesta Key Watersports
We’re hardly adventure travelers. But that’s not gonna stop us from recommending adding 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.
(That’s more to our own style, to be honest!)
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.
No, we won’t sugarcoat it: This place screams dive bar. But we still think an evening here is a must-have experience while visiting the island!
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? We found plenty of other snacks on the menu at Siesta Key Oyster Bar, 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.
A scene straight out of Cast Away, Beer Can Island is also full of color and visual contrasts. We love how the turquoise colors collide with the forests while the fallen trees feel perfectly out of place in such a fairytale-like environment. We recommend bringing a 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, Anna Maria Island, an hour north of Siesta Key, has answered your prayers. Although we recommend staying longer, a day trip to Anna Maria Island lets travelers visit a unique coastal community with a storied past and plenty of tourist attractions.
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 our favorite activities here 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 on your itinerary, return to Bean Point in the evening for a magical sunset.
Another beach to add to your Anna Maria Island 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, we love visiting the beautiful city of Sarasota whenever we’re in the area and think that it’s well worth exploring in its own right.
For a splash of urban life and culture, cross Sarasota Bay for a great and quick escape from Siesta Key. Among our favorite 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.
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, in our opinion, add a fun layer of atmosphere to Venice Beach.
Once 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, we also found plenty of 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 quieter stretch of white sand than Siesta Key, Anna Maria Island, and Venice. (Not that we’re complaining!)
Our favorite spot on Lido Key is its 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; we think 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 horde 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 of our favorites…
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, the amenities include barbecue facilities, shuffleboard, and free WiFi.
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
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. There’s a handful of other amenities at this hotel, too. We particularly dig the heated outdoor pool.
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 are several beach restaurants and shopping boutiques. For a self-catering stay, take advantage of the resort’s free grocery delivery. We’re also big fans of the free 2-hour bike rentals for exploring more of the island.
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