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THE PERFECT 4 DAY ITINERARY - SIESTA KEY

Updated: Jan 21, 2023


Sunset on Siesta Key Beach

DAY 1

Arrive and settle into your home for the long weekend. Then start off right by heading to Happy Hour at Daiquiri Deck on South Siesta Key for half off Daqs from 3pm-7pm to put you in the vacation mood! Next, head right across the street to Captain Curt’s for dinner. Enjoy their new beautiful outdoor dining area and really good menu! After your belly is full, make your way down the street for an after dinner drink at Sniki Tiki or Crescent Club.

Smoothie from Crescent Beach Market

DAY 2

Start your day by fueling up at Toasted Mango for breakfast. Then head to Crescent Beach Market to pick up grab-and-go sandwiches for lunch later. Make your way to Turtle Beach to stroll along the water–maybe all the way to Point of Rocks–or relax in the sand. Ready for a snack and a cocktail? Head to Turtle Beach Grill for Happy Hour– appetizer and drink specials everyday 3pm-6pm. After, catch the sunset over the gulf back on Turtle Beach. Head back home to freshen up for the night, then jump on a free ride to downtown Siesta Key. End the night busting a move at Beach Club or Gilligan’s.

Turtle Beach

DAY 3

Maybe you’re slow to rise, but when you’re ready, head to Mojo Risin for a caffeine fix and a pastry to start your day. Then get settled on Siesta Key Beach for the day. Relax in the beautiful white sand and admire such a lively place. Before the hangry can set in, head back and get ready for your dinner reservations at Ophelia’s. End the night satisfied after devouring all the goods!

DAY 4

Once you pack up, set out for your last adventure. Head into downtown Sarasota and get brunch at the amazing Kurtos Chimmey Cake & Bread. This is the best sandwich place, so savor every bite of your last vacation meal!



Want more, or planning a longer trip? Be sure to check out our Travel Guide!


Well there you have it–the perfect four days in 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!

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