top of page


Updated: Jan 29, 2023

Cheesin' on Siesta Key Beach

Once upon a time…(last month)…I was enjoying some cocktails at the Downtowner in Baraboo with my best friend, Ellie, who was in town visiting from Colorado. In our tipsy state, we were talking about how we needed some sunshine. I instantly thought, “Why don’t we go to Mom & Dad’s condo?!” Right then and there, we cashed in our Southwest points and booked a trip back to one of my favorite spots–Sarasota, Florida.


Sarasota County is home to a lot of amazing beaches and awesome beach towns, but my favorite is definitely Siesta Key. I adore Siesta Key. (The place, not the show–IFYKYK 😂) It’s the cutest island that has everything I need on a vacation. I often refer to it as “my happy place.”

I am a lucky gal…

My parents have a condo in Sarasota (near Siesta Key) that they plan to retire to someday soon. They’re not quite to full snowbird status yet, but they visit often during the winter months. My grandparents used to live just outside of Sarasota, so we used to visit them in the winter or over spring break when I was growing up too. In the past few years that my parents have had their place here, my mother is constantly encouraging Hayden and me to use the space. We do our best to take advantage of it!


Here are the best spots I’ve found in Sarasota County over the years!


My favorite vacation activity is chilling on the beach. This area is loaded with beautiful spots to relax. Here are 4 incredible gulf beaches:

SIESTA KEY BEACH: Voted the #1 beach in North America, this dreamy beach will not let you down! The incredible white sand is some of the softest ever, and it doesn't get hot and burn your feet. There’s a massive public parking lot, but it often fills up fast, so you have to be an early bird to get there in time to snag a spot. This public beach has lifeguards and a snack bar where you can grab concessions or a daiquiri.

CRESCENT BEACH: Tucked away in the middle of the hustle and bustle, you can find a small parking lot that provides access to the gorgeous Crescent Beach. If you can get a spot in the lot, it’s so convenient, because it’s right near some bars, restaurants, and the grocery store. It can be nice to leave the beach for happy hour or to watch the sunset without having to move the car or walk far! Crescent also has beautiful white sand. It’s home to the crazy mansion you might have seen in the early seasons of the show ‘Siesta Key’ and a cool spot you can walk to called Point of Rocks. This would be an excellent place to fish or snorkel if that’s your jam.

TURTLE BEACH: To the south, on the less-busy end of the key, you can find my personal favorite beach. Turtle Beach has darker sand for the island, but it’s still soft and beautiful. There are copious amounts of unique shells and even the occasional sand dollar. This is also a great spot to fish or relax, as it’s much calmer than some of the other beaches on the key. It’s usually much easier to find a parking spot here too. On one side of the parking lot is the gulf beach, and on the other side is the Sarasota Bay.

VENICE BEACH: About 30 minutes south of the Sarasota/Siesta Key area, you will find beautiful Venice! This beach has a massive parking lot adjacent to Sharky’s, a fun beach side restaurant, and we’re always able to find a spot. The massive fishing pier is free to access 24/7, you’re able to fish without a license from it, and they even rent fishing equipment there. Sharky’s is a great spot for happy hour and tiki vibes, and just a short walk south from there you can find Paw Park, a dog-friendly beach area! Definitely worth the walk down to see all the happy beach floofs!

HIDDEN GEM: Beach Access #8 of Siesta Key Public Beach is my favorite place to watch a sunset! There’s a very small parking lot, but even if you have to park Downtown Siesta Key in the village, it’s worth the walk. You’re still on that white sandy beach, but there’s a nice point that makes for great sunset photos. There are also sand dunes and beached sailboats that can make for gorgeous photo backdrops. It’s a dream hidden gem!

SKOB Happy Hour - 2 dozen to start!


If you ask me, every day of vacation needs a killer happy hour. Siesta Key Has so many good ones! My favorite is Marina Jack’s Blue Sunshine Patio. Their happy hour is Monday-Friday 4pm-6pm. I love the $6 cocktails, but they take the cake with their $7 meals. You can get different sliders or tacos with a side of fries for only $7–Such a delicious deal! Hayden’s favorite is SKOB– Siesta Key Oyster Bar. Their happy hour is daily from 3pm-6pm and includes ½ off dozen oysters. That means right now you can get a dozen oysters for only $10! A great deal and they must be good because I’ve watched Hayden crush 3 dozen in one sitting before. Our family favorite is Daiquiri Deck. They have locations all over the area including two on Siesta Key. Their happy hour includes ½ off daiquiris! At their current price, this makes them only $4.50 from 3pm-7pm!


BREAKFAST: 5-O Donut Co is always a treat! They have lots of fancy, fun donut flavors that never disappoint. Toasted Mango Cafe is great for a sit down breakfast and everything I’ve had there was amazing. The pancakes with mango butter are to die for!! Heads up– there can be a wait on the weekends.

LUNCH: Spearfish Grille is a patio tiki restaurant that serves up some incredible fresh fish. They are reasonably priced and everything is so fresh and delicious. Hayden discovered Kurtos Chimmey Cake & Bread in downtown Sarasota when he was here on a boys trip, and they make some of the best sandwiches EVER! I highly recommend checking them out. They make their sandwiches with Hungarian chimney cakes–curled bread that’s shaped like a hollow bread. It’s a must-try and a fan favorite with our group. Crescent Beach Market can be a great stop to pick up food to bring along for a beach picnic. They have fresh grab-and-go deli sandwiches and yummy, tropical coconut water smoothies served in the coconut!

DINNER: I couldn’t do a blog on Sarasota and not include Owen’s Fish Camp. This is one of my favorite restaurants of all time. Fish Camp opens at 4pm daily, and it can fill up fast, so there’s often a wait, but trust me, it is so worth it! Ophelia’s on the Bay is on the south end of Siesta Key. Hayden and I can both say that this is one of the best meals we’ve ever had! It’s definitely fine dining and I recommend reservations, but everything we tried was fresh tasting and completely amazing. Hayden highly recommends Steak Tartare and I recommend the Lobster Bisque.


I’m not a coffee drinker (I know, I’m strange) and Hayden doesn’t seek out coffee, he’ll just drink it if it’s readily available. On my most recent trip, I brought in the coffee expert, my friend Ellie. She tried a bunch of different places, but Mojo Risin won the favorite spot!

bike rental to explore the island


As much as I love to just sit or walk on the beach, I’m always up for an adventure. I love to rent a bike and explore the whole island on wheels! I always rent from Siesta Key Bike & Kayak because they only charge $25 for a 24 hour bike rental. It’s a fun way to explore and check out some of the huge incredible homes on the key. At Turtle Beach, there’s a boat launch where you can rent kayaks and paddle boards to explore Sarasota Bay by water. If you want to go boating in Sarasota Bay, CB's Saltwater Outfitters is your place! They are so kind and located right on the water. My dad frequently stops in there for bait and rents from them whenever he wants to fish offshore. Hayden and his friends have also rented from CB's for their boat day and had so much fun on the water!


Our go-to area for going out is usually “downtown” Siesta Key, which is technically the Siesta Key Village. It’s the most convenient option for us because we can go right from the beach, to drinks and snacks at happy hour, to the bars! We really like the Beach Club. They usually have live music followed by a DJ, and the star of the show is the giant gold shark they have hanging from the ceiling. Sometimes there’s a cover, but they have happy hour everyday from 12pm-7pm. Gilligan’s is a fun tiki bar option that often has a DJ. Another area for going out is Downtown Sarasota. Mattison's has some of the best people watching you will ever see! Lots of retirees getting down on the dance floor to live music–it’s so much fun! Directly across from Madison’s is Gator Club, which usually has live music for a cover fee. It’s a really cool old space that has lots of character!


Siesta Key has lots of free ride options to get you from one end of the key to the other. I highly recommend utilizing this if you plan to stay on the key— it’s very practical to not need a car during your trip. Here is the full list and what to expect! If you’re looking to get a little adventurous or get out into Sarasota, you can rent a moped from Siesta Key Bike & Kayak. Hayden and I love to bop around on a moped whenever we’re on vacation!

Southwest flys to both SRQ & TPA


The closest airport to fly into is SRQ, the Sarasota/Bradenton airport. This is the best option–it’s a smaller airport and just 20 minutes from Siesta Key. (If you are flying from Madison, WI, you will almost always have a layover to get to this airport, but it’s worth it to me to have such a short commute once you land.)

The other option is to fly into Tampa–TPA. There are almost always direct flights to TPA from Milwaukee, and these flights are usually cheaper than flying into SRQ. However, it’s a little over an hour drive from the TPA airport to the Sarasota/Siesta Key area.


There are some amazing rentals on Siesta Key, and the prices can vary significantly. My aunt has used El Presidente Condos, and it’s a great space with a pool and private beach access. This Airbnb looks amazing, and I admire it everytime I pass by it. My parents used to stay at Fisherman’s Cove on Turtle Beach before they had their own place. Unfortunately, I have not personally stayed at these places, so I can’t review them myself.

Well there you have it–all our favorite spots in and around Siesta Key! If you have any questions, let us know, and we will be happy to help you plan your adventures. Be sure to follow us on Instagram for more travel guides and adventure inspiration!

One of my favorite photos -Beach Access #8


bottom of page