Across the street from the #1 Beach in the U.S.

Siesta Key Beach is commonly rated the # 1 beach in the United States for good reason! With its soft, powdery white sand, huge 8-mile stretch of beach, and constant activity in and around Siesta Key itself, there are many reasons to fall in love with Siesta Key.

Things to do "in and around" Siesta Key:

Siesta Key Family Vacation: Best Time to Visit

The beauty of Siesta Key is that it can be enjoyed year-round and is visited by thousands of vacation-goers throughout every season.

With temperatures averaging around 70 degrees, many people love to visit Siesta Key in the fall, winter, and spring months. The mild, comfortable temperatures and predictable weather make this a great time to enjoy the beaches, watersports, and other Siesta Key activities.

For those looking to get away during the summer months, Siesta Key offers the same great attractions but with higher temperatures and humidity levels.

Temperatures range in the 80s and 90s from June – September, making these both the hottest months, as well as the most ideal months to swim in the gulf.

The following Siesta Key family vacation itinerary can be executed and enjoyed regardless of what month you plan to visit!

Siesta Key Family Vacation: Day 1

Arrive in Siesta Key, Florida

Check-in to your Siesta Key lodging

Head to Siesta Key Village and explore options on where to reserve your weekly beach rentals

Walk down Ocean Boulevard to window shop and find stores or boutiques that pique your interest

Have dinner at The Old Salty Dog in Siesta Key Village

Arrival

We never recommend planning too much to do on the first day of a family vacation. Arrival day (Day 1) should consist of checking-in to your lodging and getting acquainted with your immediate surroundings.

Get to know the local area before venturing out to explore and experience the sights and attractions that draw you away from your overnight accommodations.

Determine where you will get your morning breakfast and coffee. Are there late-night bars and restaurants nearby? Do you have access to the amenities that you’ll need throughout the week?

Finally, check out the onsite pool and work-out facility, or nearby beach and park trails in order to establish what to do during your downtime, and where to get in your daily exercise.

Siesta Key Village

In addition to its famous beaches, Siesta Key Village is the heart of any Siesta Key family vacation! For this reason, getting to know your way around Siesta Key Village is recommended on the first day of your Siesta Key itinerary.

Siesta Key Village is a hub of beachy bars, restaurants, shops, as well as (beach and land) sport rental outfitters located in the center of the island, only a few blocks away from the ocean.

Apart from your lodging, which may or not be located in the village, the majority of your vacation will be spent in Siesta Key Village when not at the beach.

Additional planning tip: The main street in Siesta Key Village is Ocean Boulevard.

All of the restaurants and bars mentioned in this Siesta Key itinerary are located within the city blocks of Siesta Key Village on or around the main street.

Siesta Key Family Vacation: Day 2

Take a morning walk to Meaney’s Mini Donuts in Siesta Key Village

Check out week-long bike, beach chair, and beach umbrella rentals from Robinhood Rentals (or the business of your choice)

Grab your beach essentials and spend the day at Siesta Key Beach

Enjoy “Big G’s Happy Hour”, live music, and dinner at Siesta Key Oyster Bar

Watch the sunset at Sunset Point (Siesta Key Beach Access #2)

Siesta Key Beach

The highlight of Day 2 of your Siesta Key family vacation is spending the day at world-famous Siesta Key Beach!

Siesta Key Beach, also known as Siesta Beach, is the most popular beach in Siesta Key, Florida. Likewise, it was rated the #1 beach in America by TripAdvisor users in 2015, 2017 and 2020.

The sugary-white sand found here is literally out-of-this-world amazing and is what draws families and vacation-goers here year-after-year.

The full line-up of amenities offered at Siesta Key Public Beach include:

First aid center with lifeguards on duty year-round

Public restrooms and showers

800 car public parking lot

Full-service snack bar and gift shop

Picnic areas with and without cover

Gazebos and shelters that can accommodate 60-120 people.

Families can also enjoy all the following sporting activities at Siesta Key Beach:

Playground equipment

A tennis court complex

Volleyball courts

A 20 station fitness trail

Sunset Point

Another one of the most popular things to do on the island of Siesta Key is to watch the sunset!

Since the island of Siesta Key faces West out into the Gulf of Mexico, you’re always guaranteed a front-row seat to watch the sun sink below the horizon.

Though there are many places to catch a sunset on Siesta Key, the best lookout point is at Sunset Point.