The Caribbean of America; A Guide to Sarasota, Florida

Thanks to my mother, who moved here when I left for college, Sarasota, Florida has been my second home for the past 17 years. I have curated a perfect weekend for an amazing sun-soaked, relaxing, but hip getaway. 

How to Spend a Weekend in Sarasota, Florida

Why come to Sarasota?

Sarasota, Florida has definitely changed and is changing as I write this article. I have been coming here since 2000 when my mother moved to Sarasota when I left for college. At that time, this was the quietest beach town I had ever seen. A taxi driver once asked me what the hell I was doing here since I was clearly under the age of 65… He then told me he likes to think of Sarasota as “God’s waiting room”.  Now granted, there are still 50 people a day floating up to heaven here, but I think with every natural death that occurs, two other younger people come and start a new life. It’s quite popular with the yuppies, young families, and new Wall Street money that rapidly building new condos and hotels on every corner downtown.

As of 2019, almost 20 years after my first visit,  Sarasota has gone from a quiet, sleepy town to a bustling metropolis on the West coast of Florida.

What does Sarasota have to Offer?

• Spectacular sunsets on the beach every night that’s to our west facing position
• Softest white sand on the American shores – Voted best beach 10 years in a row.
• Incredibly clean and more intelligent than the rest of our Florida neighbors.

When to Visit

• Anytime from October to May is lovely. March and April are the busiest. June and July are the hottest but can’t go wrong anytime out of hurricane season.

Where to Stay

• For the hippy, beach lover check Airbnb for tons of motel-like beach shacks a block off the sea.
• For the jet-set, the brand new Westin Hotel centered between the beach and downtown Main Street.
• For the elegant beach elite the Ritz Carlton beach club on Lido Key.

• John Ringling Causeway Run  Probably one of the prettiest and most effective runs you can find. Park your car under the bridge by the fisherman’s shack and run over the bridge at least 4 x back and forth. You will have a full sea view of the glitzy Sarasota bay-front and the beautiful homes on the Key. And it’s a big arch so really good for the butt.
• Lido beach Run  Sunset is lovely and it’s about 3 miles back and forth to take a sand jog along the sea. If you time it right you can end at the Ritz beach club for a reward margarita at sunset
• Ringling Museum  One of the oldest and most elegant places to wander around in. A stunning rose garden, original artwork, and costumes from the circus, and much more.

Where to Eat

• Owens Fish Camp is my all time favorite spot. It’s a Florida house transformed into a lovely homey restaurant with a huge outside garden. They have live music on weekends and a backyard bbq to have snacks and beers while you wait for your food. You will feel like a local after the first beer and shrimp skewer.

• Blue Marlin all the way out on Anna Maria Island which is technically Bradenton (Sarasota’s more local and humbled neighbor) totally different vibe but the most elegant restaurant on this beach. 1920’s Captain fish house turned charming restaurant. Resembles New England more than Florida and absolutely great. Wonderful service, cute atmosphere, and good food.

• The Shore I believe the first really cool place to open in Sarasota and is still going strong. An awesome boutique clothing/ surf shop below the restaurant gives this LA-style eatery a young hip vibe. Definitely the best looking crowd in town and the most glamorous (beachy) scene

• The Lido beach Pavillion Snack Shack I wish I was kidding with this one but the dude who works the grill at the beach bar makes the best fish tacos and lobster rolls in town. Def the story of don’t judge a book by the cover. Once a seagull dive-bombed down and stole the lobster roll right out of my hand while walking back to my towel. I cried for like 10 min. (Then Dude made me a new one:) best lunch hands down. Also the cheapest lunch in Sarasota, Florida.

Where to Drink

In Florida, I believe you should only be drinking w a view of the water otherwise what the hell is the point to go to Florida. Go back to NYC.

• Ritz Carton beach Club Tiki bar on the sand open to the public. Excellent margaritas and an awesome place for sunset drinks.

• O’Leary’s Tiki Bar This is a daytime bar spot but if you’re not drinking in the day Did you even go to Florida? Imported sand palms and tiki bar in the park on the Bay of Ringling Blvd. The poor man’s Caribbean but a great way to kill a Tuesday. 

• The Beach House Though very crowded in peak season this is one of the only proper restaurants directly on the sand. It’s up in Anna Maria Island but if you want to have a drink and eat something while sunset-gazing this is one of the only casual spots with drinks and food on the beach. Food is ok, drinks are better, Sunset is wonderful.

Where to Shop 

• Besides the trendy best swimwear designers at The Shore, I find great joy in Vintage thrift shopping in Sarasota! My favorite place is The Pines of Sarasota which is just a big thrift shop but full of treasures.

Beautiful You Boutique -With a little patience and creativity you can walk out with some sick vintage pieces and maybe an old high-end designer item if you’re lucky. My friend once found vintage 1960 Christian Dior Sunnies for $1. I think she sold them for 400 on Etsy.

This beautiful spot on the west coast of Florida is a great place for a couples trip, family vacation, or just quick sunny getaway. Flights to Sarasota are direct from many major cities and the airport is lovely. Why go to the Caribbean when Florida is so close? Hope you enjoy my guide to Sarasota, Florida. Comment if you have ever been here or anything to add!

Love, Lyla