The Ultimate Siesta Key Family Vacation | Itinerary + Tips For Your Visit

Look no further for the best all-encompassing Siesta Key family vacation itinerary for spending 1 to 6 days in Siesta Key, Florida!

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.

In this post, you will learn all about what to see, how to get around, and how to plan the absolute best Siesta Key itinerary when visiting Siesta Key with or without kids.

Likewise, we’ll show you the best Siesta Key restaurants, attractions, and watersport rentals that will fit perfectly into your Siesta Key family vacation itinerary,

This post may contain affiliate links, which means that we may receive a small commission, at no cost to you, if you make a purchase through a link. For more info, see disclosure.

Siesta Key Family Vacation: Best Time to Visit

Siesta Key is located on Florida’s Gulf Coast adjacent to Sarasota, Florida in the United States.

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 plan a Siesta Key beach vacation 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 to August, making these both the hottest months, as well as the most ideal months to swim in the Gulf.

In order to make these months more tolerable, it is important to understand how to stay cool in Florida as the heat is quite intense.

Additional planning tip: Be mindful that Florida’s Hurricane Season runs from June 1 to November 30, with the peak of the season being the first week of September.

And psst…check out our related posts before your trip:

• 33 Best Things to Do in Siesta Key While on Vacation
• Best Seafood in Siesta Key: 8 Must-Try Eateries!
• 11 Best Overall Restaurants in Siesta Key That You Must Try!
• Siesta Key Parasailing: A Complete Guide For Kids & Adults

Siesta Key Vacation Itinerary Ideas

Below you can find suggested Siesta Key vacation itinerary ideas from one to six days.

The itinerary suggestions are based on our personal experiences and are filled with insider travel tips for visiting Siesta Key for the first time.

No two Siesta Key vacations will be exactly the same, however, so use these itinerary suggestions as a guide.

You’ll need to adjust your itinerary as needed to account for weather, where you stay, how much time you spend at each attraction, and the varying interests of your travel party.

Also, be sure to consult our Florida packing list before your trip to be sure that you pack the correct clothing, accessories, and necessary Florida extras for when you plan to visit!

*All of our top recommended family-friendly restaurants, landmarks, and attractions are bolded. Their physical locations fit into the flow of this itinerary. If you choose to substitute a restaurant or attraction in their place, be sure to adjust the timing of your itinerary accordingly.

Siesta Key Family Vacation: Day 1

• Arrive in Siesta Key!
• Check in to your Siesta Key accommodations.
• 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.
• Grab a waffle cone at Big Olaf Creamery.

Arrival

We never recommend planning too much to do on the first day of a family friendly 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 home to the best Siesta Key bars and restaurants, shops, and (beach and land) sport rental outfitters.

It is 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 Meany’s Mini Donuts in Siesta Key Village.
• Check out a week-long bike, beach chair, and beach umbrella rental 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 the 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 and turquoise waters found here are 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 includes:

• 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 court
• A 20-station fitness trail

Additional planning tip: Siesta Key Beach is located 2 hours south of Disney World in case you’re wondering about the closest beaches to Orlando.

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 Sunset Point.

Located at the north end of Siesta Key Public Beach, this jut of land offers one of the best views of the magnificently lit evening skies.

Though you can see gorgeous sunsets anywhere along Crescent and Siesta Key Beach, Sunset Point is a fun gathering spot where many other tourists come together each evening.

In fact, you may find yourself returning here every night of your Siesta Key family vacation!

Additional planning tip: Keep a close eye out, for there’s a possibility that you’ll catch a rare sight known as a “green flash”. The green flash is a quick spot of green seen at the top of the sinking sun. 

Siesta Key Family Vacation: Day 3

• Take a morning beach walk and collect shells.
• Head to CB Saltwater Outfitters and grab a half-day (4 hr.) boat rental; Cruise around the Gulf of Mexico and hang out at Big Pass Sandbar.
• Enjoy the sights and scenes of Siesta Key from above the water on a parasailing adventure at Parasail Siesta!
• Get freshened up and head into Siesta Key Village for dinner and drinks on the patio at The Hub Baja Grill.

Siesta Key Water Rentals

Day 3 of this Siesta Key family vacation itinerary involves getting out to enjoy and explore the Gulf of Mexico via watersport rentals.

Popular watersport activities in Siesta Key include kayaking, parasailing, jet-skiing, and boating.

No need to look too far, because Siesta Key is home to several watersport outfitters that have ample equipment and guides to make for the perfect ocean outing!

Out top recommendations for Siesta Key water sport rentals are listed here:

• Parasail Siesta – Parasailing ($90/flyer)
• CB’s Saltwater Outfitters – Jet ski and boat rentals (family-owned and operated)
• Siesta Key Jet Ski – Jet ski rentals
• Siesta Key Aqua Adventures – Banana boat and aqua spinner rides
• Robinhood Rentals – Paddleboard and kayak rentals
• Siesta Key Paddleboards – Paddleboard rentals

Read here for our complete recap plus photos story about parasailing in Siesta Key! We provide a complete guide to Siesta Key parasailing as well as tell you where to go, what to wear, and answer, “Is parasailing scary?”.

Siesta Key Family Vacation: Day 4

• Enjoy breakfast and coffee at Another Broken Egg restaurant.
• Relax on Crescent Beach and go snorkeling at Point of Rocks.
• Return to your beachside accommodations to freshen up.
• Rent an electric scooter or scooter car from Ride & Paddle and cruise around the island.
• Have dinner at the Lobster Pot Restaurant.
• End the day with drinks and live music on the Daiquiri Deck in Siesta Key Village.

Crescent Beach at Siesta Key

After dinings at Siesta Key’s most popular breakfast hang out, Another Broken Egg, and get ready for an ultra-relaxing day by heading to Crescent Beach.

Crescent Beach is the most private, non-private beach in Siesta Key and is quieter and more secluded than its counterpart, Siesta Key Beach.

This part of Siesta Key is an enclave where the beach is densely lined with condos, villas, and vacation rentals that provide direct access to the waterfront.

Midnight Pass Road provides the only (easy to miss) public access to enter Crescent Beach. From there, there’s a 25-space parking lot and walking pathway that leads out onto the beach.

Though it doesn’t have the same amenities as Siesta Beach, you can still go shelling, build sandcastles, and enjoy the ocean with a bit more privacy.

In addition, Siesta Key’s diving and snorkeling hotspot called Point of Rocks is located at the southern tip of Crescent Beach. This is where you’ll spend the next hour or so during this itinerary.

Siesta Key’s Point of Rocks

Though a bit difficult to get to, the Point of Rocks is known as the best place to snorkel in Siesta Key. It is also one of the best family activities in Siesta Key.

The easiest way to find Point of Rocks is to walk to the southernmost end of Crescent Beach until you reach a gigantic sea wall. You must then climb along the sea wall, turn a corner, and walk down 3 steps into the water.

By now you will see the amazing tide pools and snorkeling area complete with an array of gigantic moss-covered rocks that protrude from the ocean.

The water is no more than 5 feet deep here, and there is a vast amount of marine life that includes fish, crabs, and red sponges.

The shallow water makes this a perfect place for kids/beginners to snorkel with a basic retail store snorkeling set.

There are also large distributions of seashells, making this a perfect spot for shell picking.

Additional planning tips: Wear water shoes when visiting Point of Rocks as the terrain is made up of crushed shells and coral. Also, the rocks can get quite slippery.

There are only 10 – 12 parking spots at the alley access for Point of Rocks. This is why it is best to park at Crescent Beach and walk from there.

*Click the image to get our exclusive FREE Family Vacation Packing List that is both customizable and printable!

Siesta Key Family Vacation: Day 5

• Get coffee and crepes at Bonjour’ French Cafe.
• Take a 2-hour Dolphin and Sea Life Tour from Siesta Key Marina.
• Drive 15 miles South to visit the “Shark Tooth Capital of the World”, Venice Beach, Florida.
• Shop through downtown Venice. Spend time at Venice Beach and end your day with dinner and drinks at Sharky’s On The Pier.

Siesta Key Dolphin Cruise

Start the day off with delicious croissants, homemade crepes, fresh-squeezed orange juice, and specialty coffees at Siesta Key Village’s Boujour French Cafe!

Next, spend the morning of Day 5 taking an unforgettable guided dolphin cruise!

By far one of the best things to do in Siesta Key is to watch dolphins jump and play in their natural environment on a guided dolphin cruise!

Siesta Key waters are home to one of the largest populations of wild bottlenose dolphins. Seeing dolphins in their natural habitat is both thrilling and serene, as well as something that you will never forget.

The beauty of taking a guided dolphin cruise is that the captain of the boat knows where to find them and will provide you with a relaxing experience to get a first-hand view.

Siesta Key dolphin cruises vary in length, time of day, and overall experience.

Venice Beach

We absolutely loved our afternoon trip to Venice Beach in Venice Beach, FL! This is why we recommend that you include a stop here in your Siesta Key family vacation!

Venice Beach is unique in that it has a high density of fossilized shark teeth that can be found ashore. There are also many opportunities to see wild dolphins here.

In addition, the beaches along Venice are home to a large number of marine turtle nests. These can be found between the months of May and October. 

Last, the perfect place to enjoy appetizers, dinner, and a drink is at the tourist hotspot, Sharky’s on the Pier!

Sharky’s is located right on Venice Beach with direct views of both the beach and fishing pier. There is indoor and outdoor seating, a gift shop, and a laid-back tropical vibe.

Additional planning tip: Visit here to learn more about where and how to find shark teeth in Venice.

Siesta Key Family Vacation: Day 6

• Drive 7 miles North to Sarasota, Florida.
• Stop to take photos at the Unconditional Surrender Sculpture.
• Visit the Circus Museum at The Ringling.
• Take a 2-hour guided kayak tour through the Sarasota mangroves with I Kayak Sarasota.
• Spend time at Lido Beach.
• Browse, shop, and dine at Lido Key’s St. Armands Circle.

Explore Nearby Sarasota

To cap off your amazing Siesta Key family vacation, consider venturing out to nearby Sarasota, FL.

Some of the best things to do in Sarasota include soaking up the fun and sun at Lido Beach, visiting the Mote Marine Laboratory & Aquarium, as well as visiting its popular shopping district, St. Armand’s Circle.

Additional planning tip: If you’re ever back in the area, you can grab our complete 6-day Sarasota vacation itinerary here!

Siesta Key Family Vacation: Getting There

Siesta Key is an 8-mile barrier island. The island is 11 miles (a 20-minute drive) from Sarasota-Bradenton International Airport and 71 miles (a 90-minute drive) from Tampa International Airport.

All major rental car companies are available at both airports. Taxis and ride-hail companies such as Uber and Lyft are available as well.

How to Get Around

In order to lighten the traffic on Siesta Key and save you the hassle of having to find a parking spot, Siesta Key offers several free transportation and rideshare options once you are on the island.

The Siesta Breeze Trolley (pictured above) offers free round-trip service from Siesta Key Village to the southernmost part of the island, with many stops along the way.

Likewise, Jonny’s Original Free Beach Rides operates a fleet of electric vehicles. They seat six and can transport your gear like beach chairs, coolers, and shopping items.

Other free, convenient, and eco-friendly transportation options include Siesta Key Free Ride and Siesta Key Frog Hop!

Additional planning tip: Some of these options require you to call and reserve a pickup time.

Also, though they are free to ride, these companies are all greatly appreciative and reliant on tips.

Where to Stay When Visiting Siesta Key

Because all of Siesta Key’s beaches and attractions are relatively close to one another, you can choose to stay in one place for the entire duration of your trip to Siesta Key.

There are several beachfront resorts to choose from that range in price and amenities.

Our favorites, which are all highly rated, include the Sarasota Surf & Racquet Club (complete with full kitchens!), Tropical Breeze Resort, Hyatt Residence Club Siesta Key Beach, and Tropical Beach Resorts.

Check out their outdoor pools and the walking distance to the beach, as well as if they have a hot tub, picnic area, barbeque grills, and other family-friendly amenities.

Compare prices and locations here:

Booking.com

For more options, consider staying in nearby Sarasota which is only a short drive away.

Though it is about a 20- minute drive from Sarasota to Siesta Key, you may find more options that suit your family’s needs. (Keep in mind that traffic congestion in Downtown Sarasota can also be an issue.)

Friends have recommended Lido Beach Resort, as well as Embassy Suites by Hilton Sarasota if you don’t necessarily need to stay oceanfront.

Siesta Key Family Vacation: Conclusion

We hope that this itinerary has provided you with fun inspiration for a Siesta Key family vacation.

My hope is for you to have an amazing and carefree experience!

Before you go, don’t forget to read these amazingly helpful family packing tips.

Last, consult our top tips on flying with kids, and road-tripping with kids (depending on how you plan to get there) to keep the kids calm and happy while traveling!

*All photos courtesy of VisitSarasota.com unless otherwise noted.

I love Siesta Key! What excites you the most about this Siesta Key family vacation itinerary?

Jen

If you like our 6-day Itinerary for a Siesta Key Family Vacation, click here to read our Related Posts:

Sarasota, Florida:

• Complete 6-Day Sarasota Vacation Itinerary For Families
• 11 Best Things to Do in Sarasota While on Vacation
• Sarasota Kayak Tours (+Best Tips)

Siesta Key, Florida:

• 11 Best Things to Do in Siesta Key While on Vacation
• Siesta Key Parasailing: A Complete Guide for Kids & Adults
• 11 Top Restaurants on Siesta Key For Families

The surrounding area:

• 11 Best Things to Do on Anna Maria Island
• 11 Fun Things to Do in Tampa Bay (+3-Day Itinerary)
• The Ultimate Orlando Family Vacation Itinerary

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*