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5 Day Siesta Key Vacation Planned For You

Planning a beach vacation certainly isn't relaxing. The stress of it all can just be too much sometimes. This is supposed to be a relaxing experience! As a local here in Sarasota, let me lay out a fantastic 5 day vacation plan for you! 

Arrival Day

I'm not planning anything for you, nor am I counting this as one of the five days. This is a day for travel and relaxing on the beach if you have the energy to make it there. Hopefully you are staying with us at Minorga on the Key Village Condos in Siesta Key Village just a few blocks from the beach. Rest up...adventure awaits!

Day One

A walk on the beach in the morning is a great way to start your day. Siesta Beach has miles of beach for you. Try to get out there before the sun comes up for special shades of reds and blues over the Gulf of Mexico.

Next, head to breakfast at Sun Garden Cafe in Siesta Key Village. You should start there because you will want to go again. There are lots of creative and delicious breakfast and lunch options available. Everything is delicious and prices are very reasonable.

Now it is time to get ready for a relaxing day on the beach. Don't forget the items you'll need and bonus points if you use one of our beach hacks!

A late lunch is exactly what you'll need after some beach time! Head down to Anna's Deli near Crescent Beach on Siesta Key for some of the best sandwiches around! The free Siesta Key Breeze Trolley can take you there from Siesta Key Village!

After a lunch at Anna's you can walk right over to Point of Rocks, a great spot to fish, watch dolphins and manatees and snorkel! 

Spend the rest of your day walking north past the Siesta Beach public area and play some beach volleyball! Beach toys and snacks are available during the day at the public beach pavilion.

Head back to wash up for fancy dinner at the Cottage in Siesta Key Village! This location has an awesome back patio that lights up when it gets dark. The food here is delicious and you can enjoy a full bar's worth of cocktails and spend the rest of your night right where you ate dinner! Talk about relaxation.

Day Two

A walk on Siesta Beach is always my recommendation to start your Siesta Key day and Day Two is no different.

On the way back, grab some mini donuts (open at 8 AM) from Meaney's Mini Donuts. You won't regret it. The Donut Experiment opens at 7:30 and lets you create your own donut if you are back early!

For this second beach day it’s time drive or walk to Shell Beach. This small beach facing Lido Key overlooking Big Pass is less crowded but has very little parking available on Shell Rd. Get there early to get your spot or take an Uber or Lyft.

Head to Siesta Key Village for some shopping, ice cream and wine tasting after Shell Beach. Siesta Key Wines does wine sampling after noon and there are lots of spots to shop all over Siesta Key Village!

When you get hungry you need to head over to Siesta Key Oyster Bar, best known as SKOB. They have some of the best food around and the drink deals are fantastic! Live music is usually happening and there are plenty of TVs to catch some games, too.

You could spend the rest of your night at SKOB or hop around to a number of the bars including Daiquiri Deck, Gilligan's, Lelu's, Hub or Beach Club 1947! We recommend a walk on the beach at night to end your second day! Let the moon & stars light your walk as you listen to the waves crash on the beach!

Day Three

It's time to explore beyond the island. We still recommend a walk on Siesta Beach in the morning! Set up a kayaking tour on Lido Key to see the mangrove tunnels. This other worldly guided tour may also include dolphins, manatees & more! 

After your tour, grab lunch and do some shopping on St. Armand's Circle! We highly recommend Columbia Restaurant for their world-famous 1905 salad! There is lots of shopping to do and plenty of unique snacks to sample!

Now is a great time to spend a few hours at Mote Aquarium just north of Lido Key on City Island. Check out sharks, manatees, sea turtles & more at this beautiful spot on Sarasota Bay!

Grab a classy dinner in Downtown Sarasota on your way back to Siesta Key. You have dozens of excellent restaurants to choose from, but if you need a recommendation we say Selva Grill.

Get some fancy drinks at Pangea after dinner and head back to Siesta Key. 

Day Four

This is a day to get back to the beach! Start your morning with a Siesta Beach walk followed by a delicious breakfast at Another Broken Egg! 

Then it's time to spend some more quality time on the beach all day. Stop by Morton's Market for some sandwiches for your lunch on the beach. This is also a great day to go parasailing, try out stand up paddleboarding or go on a boat tour! Make sure you spend the sunset on Siesta Beach watching the sun fall into the Gulf of Mexico!

After dark you can spend some more time in Siesta Key Village having a few drinks! Here are the daily drink specials, but remember to drink responsibly.

Day Five

Keep enjoying the pre-dawn beauty of Siesta Beach on your morning walk! 

It's then time to head to CROP in Gulf Gate just over the south bridge to get some juice, smoothies and snacks that will help your hangover. You can then explore "Sarasota's Epcot" in Gulf Gate with shops from all over the world and lots of gift shops & restaurants as well. 

From there it is a choose your own adventure type of day!

You can spend all day on a craft beer & rum tour

There are also a few more amazing locations to check out like Big Cat Habitat (they have ligers), the Ringling Museum & Selby Botanical Gardens if you have time on Day Five. They are all great options so don't worry about it!

End your day at Daiquiri Deck, either location, on Siesta Key. Grab a delicious dinner with some local favorites like Gator Bites & Conch Fritters. Don't forget a frozen daiquiri or two!

There are plenty of places to get ice cream before the night is over if you need some.

Departure Day

As always, start with a morning walk on Siesta Beach! From there just relax and enjoy your last hours on Siesta Key. We know we will see you again soon!

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