Siesta Key Florida is a stunning barrier island that attracts visitors looking for sun and fun in the year-round warm weather. Crystal clear water, soft powdery beaches, boutique shopping, and great food are some of the fun Siesta Key things to do.

Annually, thousands of visitors come to Siesta Key, FL looking for fun in the sun and happy memories. With so many fun things to do, let’s take a look at the top nine, so you can pick your favorites and add them to your to-do list.

1) Siesta Key Village In Siesta Key Florida

Siesta Key Village is the place to go for shopping, dining, and partying at night!

The quaint village shops are outdoors and stretch out over multiple blocks. You’ll find unique boutique shopping, souvenirs, sundries, great bars and restaurants, and just about everything you need for a great Siesta Key vacation.

There is a free municipal parking lot available at 948 Beach Road, but people often park here and then make the trek to the beach. If you are traveling during the high season, you’ll want to arrive early to get a good parking spot or come later when the beachgoers head back home.

2) Siesta Key Fishing Charters

Fishing is big in Siesta Key! You can fish from the beach, near shore within 3-4 miles, or have an adventure with deep sea fishing.

Siesta Key fishing charters are available to take you out for a fun-filled day. By hiring a professional charter, you’ll have everything you need to fish, including the license, gear, and bait. Plus, you’ll have a knowledgeable guide who knows where all the best spots are!

Here are just some of the species you might catch on a fishing charter during your visit to Siesta Key:

  • Black drum

  • Bluefish

  • Cobia

  • Flounder

  • Grouper

  • Jacks

  • King mackerel

  • Ladyfish

  • Pompano

  • Redfish

  • Snook

  • Spanish mackerel

  • Speckled trout

Finding a place to park a car has become a big problem in Siesta Key. That is one reason why Sarasota County Area Transit (SCAT) added a public trolley as an alternative to driving. In addition to being a useful form of public transportation, it is also one of the fun things to do in Siesta Key.

The Siesta Key Breeze is an open-air trolley that runs Monday through Thursday from 10:00 am to 10:00 pm. On Friday and Saturday, the trolly runs from 10:00 am to midnight.

Riding the trolley is free, and all you need to do is hop on. There are dedicated trolley stops at Siesta Key Village, Siesta Beach Park, and Turtle Beach Park. The corridor that runs between Stickney Point Rd and Turtle Beach Park is a flag area where riders can flag the trolley to stop.

Siesta Key is frequently awarded the best beach in America title by TripAdvisor, Dr. Beach, and U.S. News and World Report.

The soft powdery sand is quartz crystal white, framed by the clear blue water of the Gulf of Mexico. It’s easy to see why hanging out at this beach is one of the most popular things to do in Siesta Key.

Public facilities here include restrooms, showers, picnic areas, grilling stations, a children’s playground, volleyball, tennis, and stands selling food and beverages, including beer and wine.

For a quieter beach, visit the hidden gem of Siesta Key Florida called Turtle Beach.

5) Siesta Key Boat Rentals

Get out on the water as you navigate behind the wheel with a boat rental. Rentals at the Siesta Key Marina include fun watercraft like pontoon party boats and deck boats.

Spend a half day or full day exploring the intercoastal waterway and Sarasota bay. Search for dolphins, manatees, birds, and other marine life. Explore the beautiful sandbars and beaches of Siesta Key. Stop and swim in the warm water or have a meal at one of the great restaurants. When you are navigating the boat, the choice is yours.

6) Siesta Key Drum Circle

Every Sunday night, year-round, people arrive en mass to participate in one of the unique things to do in Siesta Key.

This fun event takes place on the popular Siesta Key Beach.

Participants form a circle while drums and bongos tap out a steady beat. You’ll see free-spirited people dancing and hula-hooping on the beach to the rhythm of the drums.

7) Siesta Key Dolphin Watching

While it is possible to spot a dolphin from the shore of Siesta Key, you have a far better chance of seeing them from the water. Head out for an adventure by taking a guided Siesta Key dolphin excursion by boat.

With a knowledgeable local guide at the helm, you can head out to the best places to see dolphins. This is one of the best things to do in Siesta Key, which is fun for the entire family.

8) Visit Siesta Key For Festivals And Events

Attending a festival is one of the Siesta Key things to do that will require a bit of planning. You’ll want to check ahead for the exact dates and times.

  • Siesta Key Crystal Classic – An international sand sculpting competition held over four days every mid-November.

  • Siesta Beach Seafood & Music Festival – This event offers fresh seafood, live music, and alcoholic and non-alcoholic beverages. The Seafood and Music festival takes place for three days at the beginning of December.

  • Siesta Fiesta – an open-air street fair with music, food, arts and crafts, handmade jewelry, seafood, and more. Located in the Siesta Key Village area.

9) Siesta Key Sunset Cruises

Watch a spectacular Siesta Key sunset without the crowds.

The sunsets over the Gulf of Mexico are famous at Siesta Key. One of the best places on land to watch the sunset is from Siesta Key Beach, but that spot draws a crowd.
You can have an unobstructed view of the sunset from your vantage point in a boat out on the water, with the Sarasota skyline in the background.

Let us take you there on a luxury boat with a bathroom onboard. At Happy Go Lucky Tours, we know the best places to create long-lasting memories while you watch the setting sun.