Blog, Travel

Styling Harvard Travels: Siesta Key

Siesta Key is one of my favorite places in the world. I first visited in 1996 and immediately fell in love. I’ve been a few times over the years, with gaps much longer than I’d like in between. I was so happy to be back again a few weeks ago for a relaxing vacation.

Siesta Key is a barrier island on the Gulf Coast of Florida. Parts of it is within Sarasota while the rest is in Sarasota County. It’s known for its amazing beaches, with Siesta Beach ranking #1 in the US.

When I first went to Siesta Key, I was lucky enough to travel with my best friend’s family to their condo there. It holds such a special place in my heart so when it came time for us to find a place to stay, I immediately looked up rentals at the complex. It has 3 pools and a private beach. What more could you ask for?

This was Jamie’s first time going to Siesta Key and I just knew he’d love it. I couldn’t wait for him to see the beach and feel the sand.

We rented a car but if you’re sticking to the general area of Siesta Key, you can easily get around using the free transportation they offer. We knew we’d be venturing out further to do some exploring so it was more convenient for us to have our own vehicle.

We spent a lot of time in Siesta Key Village. I love this little area. I once saw a commercial where they described a nostalgic-like (but different) feeling as “the feeling that has no name”. When I heard that line, I thought of some many experiences where I’ve felt the same way, and Siesta Key Village (and SK in general) give me that feeling that has no name.

Side note, if anyone remembers the commercial I’m talking about, drop it in the comments. I’ve searched for it for a few years and can’t remember what it was promoting.

We had dinner in the village several nights. We loved Cafe Gabbiano and Island House Tap & Grill, located right next to each other in the cutest little plaza.

If you’re looking for souvenirs, shirts, etc. the village is where you want to go. Beach Bazaar has plenty of options and even my favorite little drug store, Davidson Drugs, sells similar items. Walking in there is like stepping back in time. I think part of the reason why I love it so much is because it hasn’t changed since I first stepped foot in there in 1996.

There’s plenty of other fun souvenir shops down there along with The Fudge Factory, Meaney’s Mini Donuts and Made in Rome Gelato are all delicious options for a post dinner sweet treat.

Unfortunately, I don’t have any great pictures down here because I was just too caught up in the moment every time to take any.

Places to Visit

Since the weather wasn’t always warm enough for the beach or the pool, we took scenic drives.

Casey Key/Nokomis Beach

If you want to see some of the most gorgeous houses lining the Gulf, take a ride through Casey Key and end it at Nokomis Beach. Breathtaking views the whole time.

Longboat Key/Bradenton Beach

Even though it’s only about 20 miles, this ride will take you roughly 40 minutes without traffic. It’s worth it for the beautiful views and beaches, one of which is Beer Can Island, also known as Greer Island. It’s right on the edge of Longboat Key and Bradenton Beach. Coquina Beach is a must see too. You can even walk the bridge that runs right between Coquina and Beer Can.

There is parking at Beer Can Beach, but it’s limited. Coquina has loads of parking available. We visited for sunset and had I thought to bring a backup battery for my camera, would have gotten some amazing photos. I had to use my phone instead and they didn’t quite capture what I was going for.

Anna Maria Island

This beach was beyond amazing. We booked a photographer to do a sunset shoot and decided to meet there. We were able to not only capture phenomenal photos, but we experienced the most amazing sunset. I also couldn’t recommend Brittany more. She and her daughter were so sweet and she made my camera shy husband feel so comfortable.

Downtown Sarasota

A place to see for sure! This downtown is home to countless great restaurants, including our favorite, Clasico (we went for brunch and dinner), along with some great sights like the “Unconditional Surrender” (kissing sailor) statue.

It’s also a super quick ride to the very cool St. Armands Circle. You’ll pass through both of these areas on your way to Longboat Key/Anna Maria Island.

Siesta Beach

This is one place you can’t pass up. The sand is incredible, the water is clear and many times you can spot dolphins swimming just offshore.

We try and make it a habit to visit a beach wherever we travel, even in England, and this is my favorite beach in the world! Bean Point on Anna Maria Island is almost tied for first place though.

As with every vacation we take, I left a piece of my heart there. We are so fortunate to be able to travel again. It feeds my soul and my wanderlusting heart. I’ll be dreaming of the day we can get back there again.


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.