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Roam Guide / Siesta Key, Florida

Roam Guide / Siesta Key, Florida


By day, Jackie is a modern-day marketer, strategic leader and integrator with a relentless obsession with value alignment and focusing resources in one meaningful direction. In her off time, she enjoys life with her husband of 17 years and their two boys. Much of her time is spent shuffling her two athletes to games and practices, so when they find an opening between sports seasons they seize the opportunity to travel. Equal parts right and left brained she finds joy in both the planning side of travel as well as allowing time to simply stumble upon the beauty of the natural world. She’s a non-stop flight lover, so much of her travel requires locations that are easy to get to from Minneapolis. Lucky for them, MSP airport offers non-stop flights worldwide.


Siesta Key, Florida.

A seven-mile long barrier island just minutes from mainland Sarasota. Siesta Key Beach is often rated the best beach in America, due in part to it’s white as sugar, 99% pure quartz sand, that stays cool under your feet.

When to go?

Our favorite time to go is in October or for Spring Break in March, when the sea water is warm for swimming and the daytime temps are in the upper 70’s to low 80’s. After living in Tampa for 6 years I can tell you first hand that the high humidity in Florida can be quite uncomfortable in summer. If you’re considering traveling to Siesta Key during this time, be prepared.

How to get there?

You can find direct fights on multiple airlines to Tampa (TPA). It’s your quickest route with just over an hour drive to Siesta Key. An alternate option is an hour and a half drive from Ft. Myers (RSW). If you have kids or are a kid at heart and want to check out Disney or Universal Studios before or after your beach trip, you can drive to Siesta Key from Orlando (MCO) in two hours.

Where did you stay?

We stayed at a Vrbo rental right on the beach that could sleep 14, but there are many home rental options in the area, some with a minimum night stay. Many overnighters choose to stay in a rental property, but if you are looking for a resort feel, consider the Hyatt Residence Club in Siesta Key Beach. It has a beautiful beach front property and is in walking distance to an island grocery store, the fish market and ice cream. You can also catch a free trolley ride to The Village.

What should we do?

Spend the day at the beach and stay for the sunset! Siesta key is as perfect as any stretch of sand can be, it meanders for miles along the gorgeous turquoise waters of the Gulf of Mexico. There are many public beach access points and three main beaches: The award-winning Siesta Key beach, Crescent Beach which is closest to many accommodations, and Turtle Beach on the southernmost end of the island, which is often less crowded. The larger than life sunsets offer a breathtaking array of colors. You can find a spot to linger all day in the sand or you can get moving. There are bike and scooter rentals available, but if you plan to bike on the beach do it prior to 10am to avoid the pedestrian traffic. In addition to its famous beach, Siesta Key is home to a lively little village with small boutiques, shops, restaurants and bars. The village is very walkable and there is lots of free transportation on the island - it may be free but make sure you have cash for tipping. We also love the Sarasota Farmers Market, just a 10 minute drive from the island. They offer local produce, prepared foods and hand made goods from local makers every Saturday.

Where should we eat?

Start your morning with some terrific iced coffee from Lelu’s (be sure to order it with the coffee cubes!), all organic and locally roasted. It’s located in the heart of the village, so pull up a bar stool and people watch outside or enjoy the quaint and cozy interior. The breakfast is a can’t miss as well. Local eggs, ham, bread, corn tortillas and house-made Bloody Mary’s. If you are in the mood for something sweet to pair with your coffee, take a short walk to Meaney’s Mini Doughnuts. Be prepared for a long line and skip the fancy flavors. Head straight for the cinnamon sugar or powdered sugar varieties, both served hot and fresh. For dinner (and serving lunch on the weekends) don’t miss The Hub Baja. They have live music, covered outdoor seating and the best margaritas in the village but the star of the show here is their Lobster Bisque. Do NOT leave this island until you’ve tried it. Located on the south side of the island, near Crescent Beach, Orange Octupus ice cream is handmade and slow-churned on-site. A perfect ending to a day in the sun. Worth the 15 min drive off the island is the Columbia Restaurant, founded in 1905 by Cuban immigrant Casimiro Hernandez, this is Florida’s oldest restaurant and there is no denying why…The Cuban Sandwich! The “Mixto,” as it was known in the beginning, was created in the 1890s for the cigar workers as they walked to and from work. The restaurant is still using the original recipe with the same proportions placed on Cuban bread brushed with butter on top and pressed to a crispy finish.

What is the one can't miss item on your itinerary?

On the south side of Siesta Key, the Big Water Fish Market is both a retail fish market and a casual and approachable restaurant that specializes in fresh, wild, Florida seafood. We’re talking fish caught that morning and available for same day purchase. The menu changes daily as the fresh catch comes in. If you are lucky enough to be there for the hot lobster roll, snatch one up! If your accommodations have a grill, don’t leave with less than 2 lbs of fresh caught shrimp. Ask the folks at the counter what their favorites are and they will be sure to send you off with the perfect assortment. We picked up fish to grill nearly every night of our last trip to Siesta Key, sampling Triple Tail, Tuna, Grouper and multiple varieties of shrimp.

Tell us something we don't know?

Don’t be surprised if you see dolphins in plain view just off the shore. The crystal clear waters around Siesta Key are perfect for ocean wildlife viewing. Siesta Key is one of the top locations for dolphin research in the world because of the large local population of dolphins.

What should we shop for, or bring back with us?

Gidget’s Coastal Provisions has a beautifully curated collection of coastal goodies! Not your typical tourist t-shirt shop. You’re sure to find something unique to remember Siesta Key!

What should we take on the trip?

The humidity is high so plan to rock a great side ponytail or top knot and don’t forget some good hair product. I would also suggest a comfortable bathing suit and cover-up, I really love the beach shop by Boden. Below I have linked my favorite travel capris. You can wear them on the plane with a jean jacket and transition them to biking on the beach.


Click here to see everywhere Jackie recommends in Siesta Key and to read a collaborative post on 5 Florida Beach Vacations here.

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What are we missing? Tell us your favorite Siesta Key finds in the comments below.

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