The warmth and sun of Florida is a major attraction any time of year. Kick-off summer the right way with a Memorial Day trip to that fun and sun you won’t soon forget by heading to Siesta Key. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities there are to do and see. With water temperatures already pushing toward the 80s and air temperatures in the mid-80s, you’ll enjoy every moment.

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Beach Time

An island vacation without a visit to its beaches is virtually unheard of. You and your group are moments away for the luscious sand and vibrant waters of the Gulf of Mexico wherever you are. Fill the cooler, grab the beach gear, and stake your territory with blankets and umbrellas and prepare for a day of lounging on the shore, or a dip in the Gulf of Mexico.


Snorkeling is a great way to get in the water and explore the area. Whether you rent gear from a local shop and head out on your own or book a charter tour, it’s a magical way to see the underwater world surrounding Siesta Key. Adventurers looking to make their own fun should try Point of Rocks, a spot known for tide pools, moss-covered rocks, and sea life in an easily navigable area. If you’ve been missing the group vibe, charter a boat with Key Life Charters where you can bring your own snacks, including adult beverages. Expand your snorkeling adventure with them by adding experiences like sightseeing, dolphin and wildlife spotting, and more.


Gain a whole new perspective on where you’ve chosen to spend your Memorial Day and sail high over the water with Parasail Siesta. You’ll take off from the deck of their specially designed and USCG-approved parasailing boat to fly high above the waters of the Gulf. Reach heights up to 500 feet in the air! Keep watch on the water from your bird’s eye view for dolphins, turtles, manatees, stingrays, and other sea life. Stay dry throughout the flight or wear your bathing suit for a refreshing dip in the water before flying up again to come down safely on the deck. Bring your waterproof or disposable camera to capture the memories from your perspective. Parasail Siesta takes several professional digital camera pictures of your flight and will provide you with a memory card at the end of the trip so you can develop your pictures at a later time. Rides are approximately 15 minutes of air time, but the whole excursion duration depends on the number of fliers.

Paddleboard Lessons

The warmer water and air temperatures of Siesta Key Memorial Day weekend mean more time in the shimmering waters of the Gulf. Stand Up Paddleboarding (SUP) is a popular water activity that anyone can try. If you’ve never done it before, take a lesson with Siesta Key Paddleboards. They offer daily lessons at Turtle Beach Park, as well as rental gear for those wanting to strike out on their own. If you’re confident in your skills, book a guided tour of the various waters around the island, both Sarasota Bay-side and Gulf-side.

Bicycle Rentals

Siesta Key has a land area of just 2.4 miles, so there are bound to be areas where a rental car just can’t go. Instead of trying to see everything by car, get some exercise by exploring the many walking and biking trails that bring you closer to those sights inaccessible by car. You can rent bikes for everyone in the group. Single-seat bikes without gears (a.k.a. cruisers), tricycles for extra balance and basket space, children’s bikes, adult bikes with baby seats, or take a romantic ride on a bicycle-built-for-two! Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.

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Siesta Key Memorial Day Fun

When you book your fun-filled getaway to Siesta Key, you won’t be hard-pressed to find activities to fill every minute of every day while you’re here. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the day is done, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or romantic getaway all the way up to six-bedrooms for a Memorial Day reunion with friends or family.

Contact us today to book your Siesta Key Memorial Day getaway and make memories to last a lifetime!