7 Things I’m Loving in Sarasota, Florida Right Now

what to do in Sarasota, Florida
As part two of the winter weekend getaway series, I present to you: Sarasota, Florida. This is my hometown and will always have a special piece of my heart despite the muggy summers, snowbird traffic in the winters, and a reputation as “God’s waiting room.” This is the real deal on what to do in Sarasota, Florida. I know you will after reading this!

St. Armand’s Circle


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Growing up only a mile away, I worked many a summer at the ice cream stores and beach boutiques. St. Armand’s is basically a collection of specialty shops and restaurants (arranged in a circle, duh!). I go out for a walk/dinner/drinks there any time I want to feel like I’m on vacation. There’s definitely no shortage of places to eat:

  • Columbia – best Cuban food around. When you go, you HAVE to get a 1905 salad, even if it’s just on the side. Trust me on this one.
  • Venezia–Pizza place with outdoor seating. Not sure how you can beat a cheesy pepperoni pizza while enjoying some 70 degree weather in the middle of January.
  • Tommy Bahamas – I’m totally in love with their seafood here.
  • Surf Shack – TACOS! That explain it? But really, OMG the tacos here. Just do it.
  • Blue Dolphin Café – The #1 breakfast spot around. Anytime I walk by, they always have a line out the door, full of locals and tourists alike.
  • Daiquiri Deck – aka my Happy Place. Try a Green Parrot or Pain in the Ass daiquiri…a perk here is Happy Hour is 2 for 1, need I say more?

what to do in Sarasota, Florida - Daiquiri Deck

Kilwins

This is also located in the circle but 100% deserves its own line. Full disclosure: I was a former ice cream scooper at Ben & Jerry’s, but Kilwins will always have my heart. Enjoy a delicious waffle cone of Mackinac Island Fudge ice cream, crunch on some peanut brittle, or partake in a mouthwatering piece of fudge…my mouth is literally watering just thinking of the rich chocolate. One of the unique things about Kilwins is that the ice cream chefs (is that a thing?) make the fudge on a table in front of you!

what to do in Sarasota, Florida - kilwins fudge

Skydiving

Ok, so obviously not all locals skydive, but this local did, and it’s kind of insane to see Sarasota from a different angle. I did my dive over the Gulf and landed on Lido beach, so coming in I got a bird’s eye view of St. Armand’s Circle, and when I got closer to the water…several sharks. I didn’t love that part so much.

what to do in Sarasota, Florida - skydiving

Rent a Boat

And do as the locals do…motor on over to the Big Pass sandbar in Sarasota Bay. Swim, have some drinks, and make friends with your new BFFs on the island. A note of caution – there can be some serious rip currents, so please don’t drown.

what to do in Sarasota, Florida - Sarasota sunset

Siesta Beach

Voted #1 beach in the country by Dr. Beach a few years back, you have to go to Siesta at least once. When people imagine white sand beaches, it’s basically a picture of Siesta in their heads. Siesta is great for swimming, playing volleyball, busting out the paddle ball set, day drinking, people watching…do you get the picture? Basically, it’s amazing for all beach activities.

what to do in Sarasota, Florida - Siesta Key Beach

The Village

Another plus of Siesta is its proximity to the Village in Siesta Key. The Village has a cute, beachy downtown vibe where the barefoot life is encouraged. Chow down on a cheesy omelet at the Village Café, feast on oysters at SKOB (Siesta Key Oyster Bar), or start the party with Daiquiri Deck’s killer Happy Hour (yes, there are Daiquiri Decks in both the Village and the Circle and I’m obsessed with both.)

what to do in Sarasota, Florida - beach sign
Kayak through the Mangroves

One of my favorite things to do in Sarasota is to explore by water, whether that be motor boat, Sunfish, SUP, or kayak. All I know is that when I’m on the water, I’m a happy camper…possibly I was a mermaid in another life? But in any case, rent a kayak and paddle through the mangroves in Sarasota Bay. The tunnels truly are awe-inspiring (once you get over the potential for spiders dropping on your head). They form an archway to an enchanted mangrove forest where fiddler crabs scuttle across exposed mangrove roots and fish swim languidly just inches below your kayak.

what to do in Sarasota, Florida - kayaking mangroves

Plus there are palm trees, white sand beaches, and ice cold drinks all year round…need I say more? This is your guide on what to do in Sarasota.

Disclaimer: This post contains affiliate links. If you click on one and make a purchase, I might make a little extra spending money, at no extra cost to you. As always, all opinions are my own and these products/services have been found useful during our travels and come highly recommended to you from yours truly!

62 thoughts on “7 Things I’m Loving in Sarasota, Florida Right Now

  1. Oh my gosh, how have we never been to Florida? We LOVE all those things! I’m not sure about the Pain in the Ass daiquiri (is there a secret ingredient we should know about?), but after skydiving over sharks, I’d probably be tossing them back in celebration of surviving to see tomorrow.

    Dumb question, but are there crocs or gators in them thar waters as well as sharks? We love kayaking, but seriously, it seems like all the animals in Florida want to eat you!

    • Hahaha now that I think about it, we do have some aggressive animals down here. In Sarasota Bay and the Gulf of Mexico, there are definitely no crocs and there shouldn’t be any gators. The gators are more in lakes, swamps, and ponds. You should definitely visit Florida though sometime! It’s an amazing place 🙂

  2. tatumskipper says:

    Omg, Kilwins is the best ice cream. They have one in Wilmington, NC too which is the one I;m familiar with. ahhhh! I use to live in Orlando, Florida so I visited Sarasota a couple times. Would love to go back for a mini vacay!

    • Thank you, I pretty fond of it! I personally love May because all of the snowbirds are gone, it’s a bit quieter, and the beaches are less crowded. It’s definitely hot though in May, so if you want it to be a little cooler, winter would be best for you.

  3. At the beginning of this article you said “because I know you will after reading this!” and you were right! I’d like to do everything you listed (even if I’m not 100% sure about skydiving) and eat in all those places! For sure, in case of skydiving, it’s better if I eat after, than before!
    Is it safe kayaking in the mangroves? No crocs there?

    • Yes! It really is one of my favorite places in the world 🙂 And kayaking in the mangroves is very safe. An occasional crab might scurry into your boat, but my biggest worry there is a bug dropping on my head haha

  4. Garth says:

    Wow looks like you had some adventures here, I’d enjoy the kayaking in the mangroves, but not sure about the skydive haha! thanks for sharing 🙂

  5. I never realized there was so much to do around Sarasota and I even lived in Tampa for a while! I’m sad I missed out on a lot of these activities. It looks like a lot of fun. When I visit Florida again, I will have to consider these. Thanks for the tips!

  6. Not only that I wish to be in Sarasota drinking a daiquiri, but I also wish for ice cream when outside are -10 degrees. The place looks lovely, and with so many fun activities around the corner! Thanks for all the insider tips!

  7. Oh, you hit some awesome spots in Sarasota here. Kilwin’s, Siesta Beach, the Village, Columbia….yes!! And that 1905 salad…I need to recreate that at home (even though it would never be exactly the same).

  8. Just included Sarasota on my bucketlist for when I’m visiting Florida this spring 😛 although no kayaking for me if there’s even the slightest risk of a spider dropping on my head 😀

  9. If I had ever been an ice cream scooper at Ben and Jerry’s I’d be so fat! I’ve never heard of Kilwins but you have disclosed that you are an ice cream expert so I’ll find one next time I’m in Florida.The skydiving aerial shot is brilliant, it must have got your heart racing up there. The kayaking through the mangroves would relax you again I guess.

  10. Never been to Florida before but right now when in London are -7 degrees I wish I was on the beach, enjoying a cocktail while the sand is burning my feet. Great photos, it seems you are having loads of fun in there!

  11. I was staying in Tampa with a few friends and we decided to drive down to Siesta beach to spend an evening there. It was magical and I loved the beach. However I have not done any of the other things like Kayaking. Should go to visit them soon.

  12. Chocolates and ice creams are always a tempting option in any city we visit and for that Kilwins looks something that will definitely be on the list. Kayaking through Mangroves sounds super adventurous and We never tried Skydiving but the views here look just stunning and who knows Florida may make that small wish come true 😉

  13. I have only been to the US once (or twice?) and that was two stopovers in Miami on our way to and from South America. So a total of about 2 days. I wasn’t impressed by Miami, but Sarasota sounds a lot nicer. Maybe I should consider to give Florida a second try. 🙂

  14. Sid - The Wanderer says:

    All of these look tempting, but my vote goes to skydiving! Maybe that’s where I will start, then follow up with kayaking through the Mangroves and then just eat, eat and eat 🙂

    That fudge looks heavenly! 🙂

  15. It must have been terrifying to see sharks underneath you when you skydived, knowing that you can’t control the landing and you have to fully trust your tandem partner. I have recently been maybe considering skydiving, while I was in Chile, seeing how much fun all the other travelers in the hostel were having, on their post videos. Your kayak ride looks very interesting as well.

  16. paulandcarolelovetotravel says:

    Looks a stunning place to visit with plenty to do, though think we will miss out the sky diving! #feetdotravel

  17. Wow, what a charming place to grow up in. It definitely sounds like it ticks all the boxes of fun water sports and adventure activities. Sky diving with a view of sharks sounds both incredibly fascinating and scary. How close did you get to them?

  18. travellingslacker says:

    You are surely having the tme of your life. Kilwins look delghtful. Skydiving iis not really my thing but it does look good from up there. The village seems delightful too.

  19. The view from skydiving would be incredible and I can’t believe you saw sharks in the water. We really enjoy kayaking as well so I think kayaking in the Mangroves would be something we would enjoy except if those spiders fell on us. I’ve heard of Sarasota before but didn’t have a clue what was there but after seeing this it might be worth stopping by.

  20. Lovely list of things to do. The ice cream looks ravishing and I would love to rent out a boat and take a leisurely cruise. Barefoot on the Village looks another appealing activity.

  21. We have some mangrove clumps here in south of India. I have rowed through them so I can very well relate to your experience. Every part of Florida is beautiful I have heard, great to know about this place in particular.

  22. Dane says:

    I drove past Florida a few years ago and I had no idea what to do haha I went for a few swims and then just kind of made my way up the coast. It looks like I missed a few real fun things though! I am heading back this year so I will have to check some of this out for sure! 🙂

  23. Barefoot life is encouraged?? Sounds like a dream for little me! I loved being barefoot everywhere as a child. That shark part would have traumatized me for life. I am already scared of them but actually seeing them will probably make it worse! I would need some of that Kilwin ice cream to help calm me down.

  24. Lisa (Simple Sojourner) says:

    I’m from Florida and lived in Sarasota for a time. Nice list especially for first time visitors. I love the Columbia, food is the best! So many good restaurants to choose from there. Glad you love it!

  25. Wow, I would LOVE the skydiving and kayaking. I’ve never done either, but they are definitely on my bucket list. Now I just have to find a way to deal with the sharks 🙂

  26. Florida has been coming a lot in quizzes lately so I am just taking it as a sign that I need to go! It’s one of the states that I haven’t visited yet and you have given me plenty of reasons to go! Thanks for sharing

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