The Snowbird’s Sarasota Travel Guide

So my first winter is Boston was a cold & snowy one..I had always heard the term “snowbird” but it never really meant anything to me. Until now. You go to someplace warm, to escape the cold, to break it up, and to make it a little more bearable. Us Bostonians really know how to enjoy the sun!

We did a snowbird trip to Sarasota for New Years (yes I know I’m behind on this post) but nevertheless, spending some warm days soaking up the sun is v necessary. Here’s the tips and tricks, places to eat, stuff to do, and your complete travel guide to Sarasota! And yes, I am already booking flights for the snowbird in me for next winter.

First things first..let me show off Sarasota by all the million pictures I took.

Since everyone knows I fly for food. Let’s start off with what we ate (+drank) all throughout Sarasota, FL!

What to eat:


This place is a must. Their pizza is life changing, plus they have a patio where you can sit shorts in the winter! YES PLEASE!

I got a croque madame and I think it might be my favorite..of. all. time. I don’t think I have words to describe it because I ate it so fast, I’ll let the picture speak for itself.

Lido Key Tiki Bar

This place is perfect to grab a drink, or two. And watch the sunset on the beach!

Tommy Bahama

I know this is a chain, but I am such a fan! Their blood orange margarita paired with either their ahi tuna salad or fish tacos. I love the overall experience and the decor.


If you know me, you know I’m a sucker for ice cream. And Kilwin’s doesn’t disappoint! I think it’s so fun to grab a cone and walk around. It’s right in the middle of things at St. Armand’s circle so perfect for it!


Their thai curry mussels and tuna tartare have me hooked! We went there the first night we were there, and I could have gone and ate both of those for every single meal and been happy! It was very delicious, every time we walked by it was pretty packed so be sure to be mentally prepared for a wait!

Daiquiri Deck

So to be completely honest, don’t get food here. There’s way too many good places to waste any sort of hunger (or calories) on the food. But it’s a fun place to hangout and grab a drink!

What to do:

St. Armand’s Circle

This place has great food and shopping! It’s a great place to spend an afternoon, hangout, get some good souvenirs, and more!

Lido Key Beach/Siesta Key Beach

Some of the clearest water I’ve seen. Both are voted in the top beaches in the country. I could have obviously laid there all day and been perfectly happy with the trip!

Kayak Siesta Key/Mangroves

I’m a lover of everything adventurous, so of course I thought this was so fun! Another way to see more of the city IN the water! We did Siesta Key, and on the way back it got really windy, so we woke up the next morning and felt it in our arms!

Downtown Sarasota Farmer’s Market

I LOVE a good farmer’s market, and this one is pretty big! It gets pretty packed, so I’d recommend going earlier than later. My favorite was the hot sauce and bloody mary mix from Annalida’s Gourmet Foods

If you go for New Year’s like we did, they do a pineapple drop in downtown which is AMAZING! It’s beyond crowded, but as you all know I’m a lover of pineapple’s so this was a highlight! Poor Danny was still on crutches from his broken ankle so I think he hated me secretly for needing to be right in the middle of the crowds, but he was a good sport! Per the usual.


~ XOXO, the sun obsessed, Amanda


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Hey there!

I’m Amanda, the blonde behind the blog a twenty-something year old with a love of wine, weekends, and traveling. You’ll find bits of my life, travel guides, beauty, food & of course, my pup Gatsby. I’m so happy you’re here & I hope you enjoy the blog as much I as I enjoy creating it! Cheers!


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