Seas the Day: A Dreamy 3-Day Siesta Key Itinerary

Siesta Beach was named the best beach in the U.S. and as a Floridian, I totally get it. Don’t get me wrong—there are so many great beaches in Florida that have a special place in my heart, but Siesta Beach is unique because its soft white sand is made almost entirely of pure quartz. It feels like powder and is cool to the touch, even on the hottest Florida days. It’s also just an amazingly beautiful beach. (If you don’t believe me, check it out for yourself on the live Siesta Key Beach Cam!)

Siesta Key is one of my favorite places to have a weekend getaway in Florida, so I’ve put together a sample Siesta Key itinerary for you to plan your own weekend at the best beach in the U.S. It takes about two and a half hours for me to drive there from Orlando, but if you’re flying in, you can fly directly into Sarasota Bradenton International Airport (SRQ) and be in paradise in only about 20 minutes. 

Since you’re just rolling into town, get your weekend started right and reward yourself with a visit to one of my favorite spots—Blase Martini Bar. My personal favorite there is the Peanut Butta Cup Martini. I know it sounds odd to exclude vodka from a martini, but they ditch that spirit and include peanut butter whiskey instead. They then mix in some Creme de Cacao and half & half, dip the rim in peanut butter sauce and top it with a little chocolate syrup. Yes, it is decadent, but it’s your first night in town and you deserve it. Don’t drink on an empty stomach though—they share this address with 3.14 Pi Pizza, so you can grab a bite to eat there too. 

I always like to start the day with two things: a walk on the beach and a good breakfast. I love a morning walk on Siesta Beach at sunrise because it is so peaceful to be on the nicely groomed beach, see the colors change in the sky and be able to experience the best beach in the country in such a serene way. The last time I went, I was staying near Beach Access 5 and started my morning walk there. I didn’t see many people early in the morning, but I did have several shore birds to hang out with. After your walk, head over to Toasted Mango Cafe. Their avocado toast is one of my favorite things to eat in Siesta Key and they put their own touch on it by adding sweet mangoes. 

After breakfast, take a walk through Siesta Key Village and check out some of the cute local shops. It’s a great place to pick up souvenirs for your friends and family back home. After you’re done with your retail therapy, grab a quick lunch at one of the great restaurants in that area: The Cottage. Sit outside on one of their patios and enjoy some tapas before heading out for your afternoon adventure. 

You can’t come to Siesta Key and not spend time on the beautiful sparkling water (and Siesta Key Watersports offers different ways to experience it.) If you’re an adrenaline junkie, I definitely suggest renting a jet ski and hitting the water. It’s so fun! If you’re looking for a more laid-back way to enjoy the water, you may want to check out their dolphin tour that takes you out to a sandbar. On the way, their crew will point out the playful dolphins and yes, it’s totally as cool as it sounds. They also have a VIP upgrade for this tour that includes adult beverages. 

If you thought the sunrise was nice, just wait for the main act as the sun goes down. A Siesta Key sunset is like nothing you’ve ever seen, and one way to enjoy it in a unique way is by taking a sunset bicycle tour. Sarasota Bike Tours offers a couple of different tour options like one on comfort cruisers and the other on electric bikes. Whichever way you go, you’ll definitely have a great time. After your bike tour, head over to Siesta Key Summer House for the area’s premier steak and seafood. They also have one of Siesta Key’s most extensive wine lists. Just make sure you’ve made reservations in advance. 

Once you roll out of bed, head over to Siesta Key Village for breakfast at Another Broken Egg. They have a variety of options like the Lobster and Brie Omelette and my personal favorite, the Lemon Blueberry Goat Cheese Pancakes. You can then take a stroll around the Siesta Key Farmers Market that is also there in the village. You’ll find homemade soaps, jellies, fresh produce, locally made spirits and more. 

If you haven’t filled up on samples from the Farmers Market, stop by the Village Cafe and have some lunch before heading back to the beach. They’re only open until 2 p.m., but they serve up some great salads, quesadillas and burgers. You can also try their Boom Boom Grouper, which is grilled grouper with rice, avocado, pico de gallo and their special “boom boom sauce.” After you finish lunch, load up your beach buggy and head down to Siesta Beach to soak up some sun. Chairs and umbrellas are available to rent, and I also love that they have beach wheelchairs available so that everyone can enjoy this amazing beach. My advice is to just relax and use this time to enjoy the white sand and sparkling waters on this amazing beach. 

Since you’re on the beach already, you’re in the perfect spot to partake in one of Siesta Key’s most beloved traditions: the weekly drum circle. The fun starts about an hour before sunset and has been a tradition on Siesta Beach for decades. It’s a unique and lively celebration full of dancing, drumming, and watching the sky as it starts to change colors. This isn’t something you can find at all beaches and is just another one of those special things that sets Siesta Key apart from the rest. 

After you’re done dancing to the beat of the drums, head over to Ophelia’s on the Bay to have a scrumptious dinner overlooking the water. There’s no better way to wrap up a weekend in Siesta Key than by having one last chance to enjoy waterfront views. This is a good finale to your beach weekend, but make sure you’ve made reservations in advance. 

Siesta Key is a drivable area and it’s pretty easy to get around. There’s also a free trolley that you can use as well. It’s a part of Sarasota County’s Breeze transit system and they operate the 77 Siesta Islander trolley seven days a week. The route takes you through Siesta Key, and you can download the Breeze Rider app to view the trolley’s real-time arrival estimates. 

I personally don’t think there is a bad time to visit Siesta Key. That quartz white sand is always calling my name. Many visitors from the north love coming in the winter though—and I can’t say I blame them.  It’s really cool to experience walking barefoot in white sand instead of shoveling white snow. The winter can be a busier time with the influx of snowbirds though. It also gets pretty hot in the summer, so if you’re not used to that, you’ll want to keep that in mind. If you’re looking for fewer crowds and milder temperatures, April-May and September-October may be best for you. 

I also feel compelled to share that hurricane season lasts from June 1-November 30. There tends to be more activity in Florida August-October, but I can honestly say I’ve been to Siesta Key in August with perfect weather and had an amazing time. Traveling during that time of year definitely doesn’t mean you’ll experience a hurricane during your visit, and chances are, you probably won’t. As you would before any trip, check the weather just to make sure there’s no named storms headed that direction before you jump on a flight. If it’s something you’re concerned about, you may want to consider getting travel insurance if you’re traveling during that time. Siesta Key is an amazing place though, and no matter when you visit, you will absolutely adore it!