A Complete Travel Guide to Siesta Key, Florida

A Complete Travel Guide to Siesta Key, Florida

Repeatedly named the best beach in the country, it is baffling how undiscovered Siesta Key beach still is. The white sand against the crystal clear turquoise waters of the Gulf of Mexico is jaw-dropping enough, but add in the lack of people, chill beach town, and access to Sarasota’s nightlife and you have a combo that is worth traveling for. A small barrier island off the coast of Florida’s West coast, Siesta Key has been a long kept secret of ours.

As we’ve mentioned before, Joe and I love traveling with other people than each other once in a while. While he normally goes to football games on his boys trips, like the weekend trip to Houston he did after we spent a week eating tacos in Austin, my girls and I usually opt for something a bit different – I know, we’re filling too many stereotypes here.

After years of this being a solo, family, or couple trip, I recently took a group of girlfriends down to and decided enough is enough! It’s time to share this hidden gem with the MLT community. This is the complete Siesta Key Travel Guide including how to get to the island, Siesta Key attractions, the difference between the beaches, and of course, where to eat.

Four Girls with Sun Setting over the ocean behind them at Siesta Key Beach Sunset Point

Girlfriends, Sunsets, Beaches, need I say more?

How to get to Siesta Key, FL

First things first, how do you get to this little barrier island? There are two airports nearby, Tampa and Sarasota. Tampa is a much larger airport and traditionally has cheaper flights, but Sarasota is closer.

The further option, the drive from Tampa to Siesta Key is a little over an hour and crosses the beautiful and scenic Sky Bridge en route. There are pull-offs along the highway with gorgeous views of the bays and intercoastal waterways. I’ve seen dolphins on this drive, no lie.

The drive from Sarasota airport to Siesta Key is about a half hour. While this is shorter than the drive from Tampa airport to Siesta Key, the flights are often cheaper. The best one just depends on where you’re flying in from and if your priority is time or money!

How to get to from Tampa to Siesta Key

With our eyes always on the budget (more money = more traveling HELLOOOOOO), we have always flown into Tampa. From here the easiest way to get to Siesta Key is by renting a car at the airport. The car is also the easiest way to get around the area during vacation.

If renting a car is not an option, there are Lyft’s by the plenty and a few shuttles that offer services to Siesta Key, but they take just as long and can be just as expensive as a taxi. For a similar cost, there are also private car companies who can chauffeur you down to the Key. These should be scheduled with advanced notice.

Wooden Fence with hanging pot lids and palm trees behind it

Where to Stay in Siesta Key

The Siesta Key accommodations market is limited, so this takes advanced planning. There is a small selection of hotels that are supposed to be beautiful, but we prefer to opt for home rentals when visiting. This last time around, we rented the second floor of a beach bungalow in an ideal location a block off the beach.

In terms of where to stay on the island, that depends on what you want. I absolutely loved the location of our last house. It was walking distance to Siesta Key village and across the street from a beach access point for Siesta Beach, my personal favorite of the three choices.

Additionally, the access point we used spit us out further from the crowds near the public parking area. While we lost the amenities of the main beach area–snack stand, bathrooms, and lifeguards–we felt it was well worth it to gain more solitude and never have our ocean views blocked by a neighbors umbrella.

Group of four girls at O'Leary's Tiki Bar in Sarasota Florida

Hanging with the ladies at O’Leary’s for sunset

Siesta Key Food

This list branches out of Siesta Key restaurants a bit and into the hot Sarasota food scene. While there is plenty to do in Siesta Key at night in terms of drinking and some decent food, the better food we’ve found is a short drive away in downtown Sarasota.

Sarasota Restaurants

Owen’s Fish Camp – After over a decade of visiting Sarasota, I am dutifully ashamed that this past trip was my first time ever eating here. It’s Southern food done in a pretty traditional and delicious way, but what really makes this place worth the 3-hour wait is the scene. The restaurant’s few tables are housed on an open porch and enclosed restaurant with a hokey, rustic decor that manages not to feel cheesy. The real winner though is out back where you can find a one-man operation serving up grilled oysters from a charcoal pit in the ground, $5 beers in a cooler, and fresh out the pot peel-n-eat shrimp.

They also had a pot simmering of my favorite Florida snack, boiled peanuts, that they dished out in paper cups. The night my girlfriends and I went, we were happy to wait for our table with a really good bluegrass band pumping out originals and cover tunes alike under the glow of string lights. Once we did finally sit for dinner, the meal was less impressive than everything else. While the food was good, it was not nearly as good as the outdoor snacks were. However, the vibe of this place and the food being above average was enough to leave me wanting to come back.  

Selva – Joe and I have been stopping at Selva every trip to Sarasota for years now, so I was delighted to bring my ladies here when we came. Full disclosure here, the Shrimp in Piri Piri sauce here used to be our favorite thing we had ever eaten. Every time we got it, we solidified our belief in the dish, even though we knew we probably should love others more based on where we’d eaten up to that point. Alas, the magic was finally broken after we ate our way around the world, but we still had a really great meal here this time around. 

O’Leary’s Tiki Bar and Grill – On a little park jutting out into the Sarasota Bay, this totally outdoor bar is a great spot to end the day. Yes, it has cheesy live music and fits right into the Florida tourist scene, but it also has cheap drinks and a beautiful view of the Sarasota skyline on the bay. While you can’t watch the sun actually set from here, the glowing sky against the waterfront buildings is magical enough.

Siesta Key Restaurants

Less impressive than nearby Sarasota restaurants, the food in Siesta Key village is more beach vacation sustenance than it is good. But, you gotta eat, and why go further from the beach than you need to? This is the food that is better than others if you need to stay on the island to eat.

Old Salty Dog – A half-indoor, half-outdoor, restaurant with pretty decent bar food. There are a few locations, but we went to the one on the Northern end of the strip in Siesta Village. Mainly, it’s good for some fried seafood and a beer. However the Fish Gumbo here was actually awesome, a pleasant surprise in an otherwise un-noteworthy meal.

Mini Donuts – Mini fried dough, in ring shapes, served on a skewer, AKA mini donuts! These ended up being the best food in Siesta Key in my opinion. Made fresh to order at a hole in the wall spot in the village, they come with a variety of toppings. We didn’t mean to, but the girls and I ended up eating them a couple of times during our five days here…or it could have been every day, but who’s counting? I’m a simple gal at heart, so my fave ended up being the cinnamon sugar. The iced coffee was pretty decent here as well.

Village Cafe – I don’t really care about most breakfast spots when I’m traveling, with a few notable exceptions: when we were in Southeast Asia and tasty noodle soup was the early morning option, a handmade pastry and many, many espresso shots when in Italy, and when I’m in the Southern U.S. Biscuits and gravy? Grits? This is a breakfast life I can get fully behind. Village Cafe was not the best Southern breakfast I’ve ever had by a long shot, but it did way better than I expected in this touristy little town. Another really busy place, expect to wait here in the mornings.

Back of Girl in Blue Kayak with Paddle in Mangrove Tunnels in Florida

Paddling through mangroves in nearby Lido Key

Siesta Key Attractions

The best things to do in Siesta Key, from kayaking the intercoastal waterways to the crazy beautiful sunsets, there is so much to do in this little waterfront paradise.

Sunset at sunset point

Living on the East coast of the U.S. for our entire lives, we get pretty damn pumped for sunsets over the water. Since we don’t regularly fly out to California, the Gulf coast of Florida has always been a treat for us. Enter my neurosis on the girls trip, the time where I got the naggiest and weird about a schedule: sunset. Hurrying us through our dinner at Old Salty Dog, I made my fried seafood stuffed companions practically sprint down the street to get to Sunset point…with a half hour to spare. Because what is a sunset on the water if you don’t have a photo shoot? The most direct view, and of course also the most crowded, is at Sunset Point.

The Beach 

As an island in the Gulf of Mexico, this one should come naturally to most itineraries. The coast here is made up of 8 full miles of beachfront, not all of which is created equal. The water here is absolutely perfect. Crystal clear, calm, and this past trip, with a nice sandbar to break up the swim out to sea. I spend hours in the water here without fail, I can’t help myself. It’s too perfect. See the breakdown of beach options below, pulled from the Siesta Key Chamber of Commerce, to decide which fits your vacation best.

  • Siesta Beach – The most popular and largest of the beach options, this is also my favorite. If you are staying off key and driving in, there are multiple parking lots along the beach. The smaller ones are tucked in between beachfront hotels and homes and only have roughly 10-15 parking spots in them, but these will give you access to the quieter parts of Siesta Beach. If you can’t find parking there, which you likely will not be able to if you get to the area anytime after 10:00 A.M., head to the large main parking lot to find a spot. This is also where the bathrooms, snack stand, and volleyball courts are if that’s important to you.
  • Turtle Beach – My next favorite beach. Turtle Beach does not have the same soft, white sand that is found on the adjacent one, but it is mellow and chill. The smaller sand space means fewer people which means quieter. I like this beach when I’m in the area alone, with a good book and a beach towel. This is also the best spot for activities with a playground, boat launch, horseshoe pit, and volleyball courts all nearby.
  • Crescent Beach – Unknown to most visitors, Crescent Beach is only accessible by a single point. The beach is here is calm and quiet with the same white sand beach as Siesta. There are rocky outcroppings in the water here that apparently makes for some great snorkeling as well.

Kayak in the Mangroves 

This was another first time experience for me that should have been in the repertoire since Day 1. Launching from Lido Key, there are many companies that offer kayak and SUP for rent to take out into the glorious mangrove tunnels, but we opted for Sea Life Kayak based on a recommendation. They were great and had single kayaks for half and full day rentals for $33 and $43 respectively. There are also tandems and SUPS if you prefer.

Sadly, we did not see manatees or dolphins on our paddle. However, the experience of floating through the mangrove tunnels, the branches intertwined above us to lend a mysterious chill to the afternoon heat, was more than enough to leave us very happy. This area does get a bit crowded, though it was pretty easy for us to have our own space by paddling out in a different direction at times. There are also tours available if you’d prefer to stick with the group.

To get to Lido Key from Siesta Key is a quick 20-30 minute drive depending on traffic. You have to backtrack off the island, cut through Sarasota along Rt 41, and turn left to cross the bridge into Lido. To get to Longboat Key, take a right once on Lido and cross the bridge onto the third local key.

Sunset Drum Circle 

Started in 1996, the drum circle at Siesta Key is its own entity. There’s even a destination for it on google maps. Held every Sunday at sunset, the wild dancing, drumming, and sense of community is fun and heartwarming. Not to mention, there’s no bad reason to watch the sunset here. See their Facebook page for up to date info or to connect beforehand if you’re skeptical.

Yoga on the Beach 

A donation based 90-minute yoga class held four days a week in the soft sands of Siesta beach. The class is a fun way to start the day. Trust me, you’ll be sweating by the time that sun is hitting the 10:30 mark in the sky. I usually hop right in for a swim after the class. The yoga + morning swim combo is guaranteed to make you feel like an actual superhero. If you are able, be generous with your donation. The teacher relies on your payments to keep this awesome practice going. Plus, you may be helping to cover a class for someone who is unable to pay for one. Win-win!

Nightlife

Sarasota has a good reputation for nightlife, though I must admit I have personally never sampled it. When we were leaving dinner on a Friday night around 12:00 A.M., the streets were packed with beautiful people cramming into dance clubs and bars with live music. I’m old, at least in spirit, so this is past my normal bedtime, but it all looks fun! Siesta Key village has a pretty good beach bar vibe with loud, bad cover bands as well if that’s more your scene.

Mote Marine Lab 

Fun fact about me: I have a deeply rooted love for Marine Biology. I studied it in college, got a degree in Ecology, and worked in the field for a few years before jumping ship (see what I did there?). I was even offered an internship here, which I desperately wanted, but ultimately could not financially afford to take. While I often daydream of going back to the work, for now, I stick to the role of visiting guest.

Mote Marine Laboratory on Longboat Key makes for a great rainy day indoor activity, but honestly, its cool enough to go even when the sun’s out. My personal favorite is to time a visit with the manatee feeding. The massive sea creatures are given full heads of iceberg lettuce which they proceed to grab between their flippers and bring to their mouths, burying their faces in each one until they’ve eaten their way through it. Can you say ADORABLE? I freak out every time, without fail, squealing in delight like some kind of deranged barn animal.

Dinner cruise on the harbor 

I used to take my grandmother out on these when I’d visit her. They’re usually held in the early evening, can have live bands, a full bar, and serve food depending on the option you choose. The boats will scoot around the Bay and intercoastal for an hour or two, with a guide pointing out historical points of interest or, mostly, the absurdly large houses of the rich and famous. The tours are a bit cheesy but they’re nice, especially when timed with those gorgeous sunsets we keep talking about. There are plenty of companies offering these, pick whichever you’re most comfortable with and go for a spin.

St. Armands Circle 

My mom LOVES St. Armands Circle and honestly, I kind of do too. It’s really touristy, overpriced, crowded, and has a lot of qualities that I don’t normally like, but there’s something about it that always makes me want to stop in on my trips to the area. Maybe its nostalgia, I’m not sure. Either way, it makes for a fun spot for shopping and wandering in a comfortable setting. Go at night for more of a vacation feel. Spend time wandering the circle and popping into shops, preferably with an ice cream cone in hand.

Go For a Beach Run 

Beach running is one of my favorite activities no matter where I am in the world. Really, any kind of running on any vacation is such a great way to explore an area. Added bonus, this is a totally free experience! This sand is great for barefoot running too if you’re into that.

Sunset over the Gulf of Mexico in Siesta Key Florida

Travel Tips for Siesta Key

There are several free ways to get around the island if you don’t want to rent a car:

*Note that “free” means a tip is expected and appreciated

  • Siesta Key Breeze Trolley – The only actual free ride, this is run by the county. It stops at what used to be the public bus route but is now this free service. The trolley can be flagged down along Midnight Pass Road. The route runs from the village all the way to Turtle Beach.
  • Johnny’s Original Free Ride – Call 941-928-9200 15-20 minutes in advance for a ride
  • Siesta Key Free Ride – Call 941 952 8294. These guys use electric vehicles making them our number one choice for rides!

Or rent bicycles! The best way to get around the island. It’s small enough to explore on two wheels, and you’ll find yourself whizzing past those sitting in traffic.

Also, there are not many accommodation options on Siesta Key itself. Hotels are expensive and Airbnb’s are limited. Book well in advance or stay off the island for a cheaper option.

Looking for another island getaway in the Florida sun? Check out Marco Island for a different vibe with gorgeous beaches.

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Girl on beach at sunset with text overlay Siesta Key Florida Complete Travel Guide mileslesstraveled.com Patio with wooden building and stringlights and trees with text overlay Siesta Key Florida Complete Travel Guide mileslesstraveled.com

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Alicia

Alicia is the wife of this duo! She loves running, beaches, and tiny animals.

3 Comments

  1. Coralie E Moorhead
    December 16, 2018 / 10:06 PM

    LOVED your post about Siesta Key and Sarasota, Alicia! Lots of good places to visit, for sure. A few other things I love:

    –The Mote Aquarium has boat tours you can take of the harbor, where they dredge the bottom and bring up sea creatures for visitors to see close up. Also a manatee rehab center in Sarasota.

    –A visit to the Marie Selby Botanical Gardens in Sarasota is well worth a visit. I’ve been there a half dozen times; twice when they had live concerts of classical music and jazz.

    –Ca’ d’Zan (Venetian for House of John) — the estate built by John and Mable Ringling, right on the Sarasota waterfront. It has an amazing art collection, wine walks, and music performances during the year. Adjacent to the Ringling Brothers Circus Museum and Theatre.

    –In St. Armand’s Circle: The Columbia Restaurant–awesome Spanish food, including the 1905 salad and yummy sangria.

    –A yes for Turtle Beach because: parking is a breeze; it has easy access to bathrooms, picnic tables and SHADE! No concession stand, but BYOF or there is a cute restaurant across the street that has a great Sunday brunch.

    • Joe & Alicia
      December 17, 2018 / 9:31 AM

      Awesome suggestions, thank you for sharing these!

      • Coralie E Moorhead
        December 17, 2018 / 6:04 PM

        You’re welcome!

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