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Look no further for the best Siesta Key family vacation itinerary for spending 1 to 6 days in Siesta Key, Florida!
Siesta Key is undoubtedly our favorite family vacation spot, and over the years, we’ve developed the perfect itinerary for visiting there!
Our itinerary covers the best things to do in Siesta Key, as well as includes the best restaurants, beach rentals, and tips for getting around the island.
In this post, you’ll learn about how to plan the absolute best Siesta Key itinerary when visiting Siesta Key with or without kids!
You don’t want to miss this post!
And psst….be sure to stick around until the end where we highlight the best thing to do on a day trip to nearby Sarasota, Ana Maria Island, and Venice Beach!
Siesta Key At A Glance
When to Go: The best time to visit Siesta Key, Florida is typically between March and May. This is when the ocean is the most comfortable to swim in and the weather is typically warm and sunny – without the extreme humidity and high summer temperatures.
Here’s a quick seasonal breakdown:
- Winter (December–February): Mild and sunny with temps in the 70s; busiest season due to snowbirds and holiday travelers.
- Spring (March–May): Best overall weather, fewer crowds than winter, great for beachgoers and outdoor dining.
- Summer (June–August): Hot and humid with afternoon thunderstorms; popular with families but more crowded and buggy.
- Fall (September–November): Warm temps and fewer tourists, but it’s hurricane season—so keep an eye on forecasts.
Where to Stay: You won’t find any huge resorts or hotel chains on Siesta Key. Instead, it is filled with smaller resorts and condos. We recommend staying somewhere with private beach access or within walking distance to the beach to avoid having to find parking. We also recommend staying within walking/bike/trolley to Siesta Key Village, again, to avoid having to find parking. Our favorite place to stay on Siesta Key is Sarasota Surf and Racquet Club. Other great options include Palm Bay Club and Tropical Breeze Resort.
How to Get Around: The easiest way to get around Siesta Key is by walking, bike rentals, or golf cart rentals, as traffic is congested and parking is limited. For longer distances, you can hop on one of the many free or tip-based Siesta Key trolleys and shuttles, which run frequently and make getting around a breeze.
Top Highlights: It’s unique, powdery white sand that is 99% quartz making it feel silky and soft; unforgettable sunsets; Siesta Key Village (the hub of bars and restaurants); its laid-back vibe; its close location for day trips to Sarasota, Ana Maria Island, and Venice Beach.
Before you Go: Siesta Beach parking fills up fast—especially during weekends and peak seasons. Arrive early (before 10 a.m.) to grab a good spot, or stay nearby and walk.
The Best Siesta Key Itinerary
Siesta Key, Florida is a paradise of possibilities involving beautiful beaches, exciting restaurants, water sports, boat tours, and unforgettable coastal city day trips.
Having a well-thought-out itinerary is essential however, as popular accommodations fill up fast and you’ll want to bundle your activities based on their location to avoid excessive driving and having to find parking.
Also, be sure to consult our Florida packing list to account for Florida’s specific weather and beach vibe.
Siesta Key Itinerary: Day 1
- Check into your accommodations. We always stay at Sarasota Surf and Racquet Club.
- Head to Siesta Key Village and check out the overall vibe! Admire the many restaurants, shops, and bars with live music!
- Have a nice dinner at Siesta Key Summer House or The Cottage in Siesta Key Village.
- Grab a waffle cone at Big Olaf Creamery or a drink at Gilligan’s Island Bar & Grill.
- Make your way to the oceanfront to catch your first sunset on the key!
The best airport to fly into when visiting Siesta Key, Florida is unquestionably Sarasota–Bradenton International Airport (SRQ).
It is located 11 miles north of Siesta Key and is a 20–25 minute drive under normal traffic. We recommend renting a car there and driving to Siesta Key.
Day 1: Siesta Key Itinerary
Upon your arrival to Siesta Key, you’ll probably want to go straight to your resort or condo to check in.
In our case, this is always Sarasota Surf and Racquet Club.
We chose to stay here for its beautiful, private beach access, spacious condos each with a full kitchen, and its convenient location to both Siesta Key Village and Siesta Key Beach.
Other great options of where to stay in Siesta Key include: Palm Bay Club, Tropical Breeze Resort, Jamaica Royale, or any oceanfront condo that meets your needs for space and amenities.
Despite where you stay, if you’re looking for ultimate convenience (and fun!), consider renting bikes for the duration of your stay, and then using them as your primary form of transportation while on the key.
Siesta Key bike rentals are very popular and most companies offer free delivery and pick-up from your resort or condo.
The roads and sidewalks on Siesta Key are bike friendly, and you can get off and park your bike just about anywhere.
We’ve had great experiences renting from both Siesta Kay Ride and Paddle and Siesta Key Bike and Kayak.
Golf cart rentals are another popular option if you’re staying somewhere parking is available.
Siesta Key Village
In addition to its famous beaches, Siesta Key Village is the place to be when vacationing in Siesta Key, Florida!
Siesta Key Village is a charming beach town district located in the center of the island, only a few blocks away from the ocean.
The streets are filled with many of Siesta Key’s best restaurants, bars with live music, ice cream shops, boutiques, and souvenir stores.
The Village has a laid-back, friendly vibe and is perfect for strolling day or night.
It’s also a hub for transportation with free trolleys and bike/golf cart rentals to explore the rest of the island.
Parking is limited here, so do plan accordingly.
Siesta Key Summer House
At Siesta Key Summer House Steak & Seafood, expect an upscale yet relaxed dining experience located right in Siesta Key Village.
Begin with standout appetizers like the creamy lobster bisque or king crab cocktail before diving into expertly grilled steaks, seafood, and signature sides.
The great atmosphere (with a huge 1,000-gallon tropical fish tank as its centerpiece!), valet service, and the fact that they take reservations, make it an ideal spot for a special night out on your first day in Siesta Key.
Afterwards, head around the corner for ice cream at Siesta-famous, Olaf’s Ice Cream or for live music and a beach cocktail at Gilligan’s Island Bar.
Siesta Key Sunsets
Siesta Key is known for its amazing sunsets and watching the sunset is literally one of the best things to do in Siesta Key!
What makes Siesta Key sunsets so unique is because of the island’s west-facing Gulf Coast location and unobstructed views of the sun sinking into the horizon.
The sky often lights up in breathtaking shades of orange, pink, purple, and gold while the reflection off of the famous white quartz sand adds a subtle glow.
It’s a peaceful, yet celebratory atmosphere along the shore as both visitors and locals gather to take photos up until the very last minute until the sun disappears.
The best place to watch Siesta Key sunsets is anywhere directly on the oceanfront! Popular spots include Sunset Point (Public Beach Access #2), Siesta Key Beach, Crescent Beach, or from your own oceanfront condo or resort.
Siesta Key Itinerary: Day 2
- Head to Siesta Key Village to grab some Meany’s Mini Donuts before having breakfast at Sun Garden Cafe.
- Spend the entire day at the world-famous Siesta Key Beach!
- If you’re looking for an activity, go parasailing with Siesta Key Watersports.
- 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).
Day 2: Siesta Key Itinerary
After a delightful morning in Siesta Key Village enjoying fresh Meany’s Mini Donuts and breakfast at Sun Garden Cafe…it’s time to head to the beach!
If your resort or condo doesn’t have private beach access – or you’d simply like to experience the hype of one of the world’s most famous beaches – pack your beach essentials and spend the day at Siesta Key Beach!
Siesta Key Beach
Siesta Key Beach, also known as Siesta Beach, has been ranked the #1 beach in the U.S. multiple times, and has even been rated #4 in the world by TripAdvisor’s 2025 Travelers’ Choice Awards.
The sand is made of 99% pure quartz, giving it a soft, cool, and silky texture that stays comfortable even on hot days.
Along with its sugary-white sand, the turquoise-colored water found here is literally out-of-this-world amazing – and is what draws families and vacation-goers here year after year.
The lifeguard shacks at Siesta Key Beach are painted in primary colors: yellow, blue, green, and red. This color-coding is designed to help people easily identify their location on the beach, especially for families with children.
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
- Beach chair and umbrella rentals available at the concession stand near the main pavilion, or through other onsite vendors
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
Free parking is available at Siesta Key Beach, but it fills up quickly—especially on weekends and during peak season (winter & spring).
Aim to get there before 10 AM for the best spots.
Siesta Key Parasailing
You’ll see plenty of parasailing taking place over and around Siesta Key Beach!
If this piques your interest, consider booking a parasailing excursion through our favorite, Siesta Key Watersports.
Read here for a recap of our entire experience and personal photos of us parasailing in Siesta Key!
Siesta Key Oyster Bar
There’s no better way to end your day than by going to one of the most popular spots in Siesta Key Village – Siesta Key Oyster Bar, otherwise known as “SKOB”.
Decorated with dollar bills on the walls and Chicago Bears memorabilia, SKOB captures a laid-back, fun atmosphere that locals and visitors love.
Siesta Key Oyster Bar features the island’s only “Oyster Happy Hour” ($8 for 1 dozen oysters from 3 PM – 6 PM every day!), and has awesome food, cold beer, and live music daily.
Favorites include award‑winning wings, grouper bites, chili-crusted tuna poke, seafood paella, and the “Siesta Key Extravaganza” (blackened mahi, jerked shrimp, crab cakes).
There is both indoor and outdoor covered-patio seating, however, it does get quite busy there so get your name on the waiting list as soon as you arrive.
…And, don’t forget to staple a dollar bill to the wall before you leave!
Siesta Key Itinerary: Day 3
- Take a morning beach walk and collect shells.
- Have breakfast at Toasted Mango.
- Reserve a half-day (4 hr.) boat rental through CB Saltwater Outfitters or book a private, chartered boating experience through Coastal Conch Charters.
- Head to happy hour (3 PM – 7 PM) at Daiquiri Deck on South Siesta Key.
- Have dinner at Spearfish Grille with Captain Curt’s Crab & Oyster Bar or Clayton’s Siesta Grille as alternates.
- Enjoy drinks and live music at Captain Curt’s Sniki Tiki or Crescent Club.
Day 3: Siesta Key Itinerary
Day 3 of our Siesta Key family vacation itinerary involves getting out on the ocean to enjoy the Gulf!
If you’re comfortable with driving a boat and are up to exploring on your own, there are several boat rental outfitters in Siesta Key that can set you up for a day on the water.
If you’d rather leave it to the experts, consider a private boat charter like we did where someone will do the driving and customize your day for you.
Coastal Conch Charters
During our most recent Siesta Key vacation, we arranged a private boat charter with Captain Aaron at Coastal Conch Charters.
We cruised aboard a luxury 26′ Sea-Ray named “One Love,” and spent a half-day on the water.
This experience can be customized to your liking, and in our 4 hours we cruised through Sarasota Bay admiring the oceanfront mansions, saw several dolphins, went shell picking and paddle boarding at Midnight Pass, and spent time playing in the water at Big Pass Sandbar.
We were able to bring our own snacks and alcoholic beverages, while a Yeti cooler with ice, along with pop and water were provided.
Spearfish Grille
Spearfish Grille, located at Safe Harbor Marina, is a seafood lover’s dream, offering some of the freshest local catches on the Gulf Coast.
Consistently voted one of the best seafood restaurants in Siesta Key, their daily specials feature fish caught within 24 hours ensuring a true dock-to-dish experience. Selections often include: hog fish, grouper, and amber jack.
Signature dishes include grilled hog fish with ginger-lime butter, sushi nachos, and coconut shrimp, as well as Spearfish Sammies and their Finding Nemo kids’ menu.
Spearfish Grille has both indoor and outdoor seating in a casual, tiki-style setting – complete with marina views and live music everyday!
Plan ahead as Spearfish Grilles does not take reservations, and on evenings with nice weather or during peak tourism, wait times to be seated can be long here.
If the wait is too long, or if you’d like different menu options, head next door to Captain Kurt’s Crab and Oyster Bar or Clayton’s Siesta Grille which are both located within walking distance of Spearfish Grille.
Both Captain Kurt’s Sniki Tiki and Crescent Club are located on the same city block as well.
Siesta Key Itinerary: Day 4
- Enjoy breakfast and coffee at Another Broken Egg.
- Take a 2-hour guided mangrove kayak tour with Kayaking SRQ
- Relax on Crescent Beach and go snorkeling at Point of Rocks.
- Optional: Rent an electric scooter or scooter car from Ride & Paddle and cruise around the island.
- Have dinner at Hub Baja Grill (casual), or Cafe’ Gabbiano (more elevated).
- End the day with drinks and live music at Daiquiri Deck in Siesta Key Village.
Day 4: Siesta Key Itinerary
After having breakfast at one of Siesta Key’s most popular breakfast hang outs, get ready for another beautiful day spent on the water!
Start off by kayaking through the mangroves, which is truly one of the most fun and unique things to do in Siesta Key!
Then, spend a quiet afternoon at Crescent Beach before heading back into the action in Siesta Key Village at night!
Mangrove Kayaking
Mangrove kayaking in Siesta Key is a peaceful, scenic, and surprisingly adventurous experience that lets you explore the island’s natural beauty beyond the beach.
Though you can rent kayaks and explore on your own, we loved our 2 hour guided kayak tour with Kayaking SRQ and consider it one of the most memorable things you can do on the island.
Led by an experienced guide, this group tour begins with a paddle lesson before heading out on the waterways.
Along with seeing plenty of wildlife, we loved paddling through the the cool shade of the mangrove tunnels and experiencing their narrow, twisty, jungle-like vibe while learning about the local ecosystem.
Read here for a recap of our entire experience and personal photos of us kayaling in Siesta Key!
Crescent Beach
Crescent Beach is a great option for those seeking a quieter, more natural beach experience on Siesta Key.
It’s important to bring your own snacks and supplies however, as facilities are limited here.
Though it doesn’t have the same amenities as Siesta Key Beach, you can still go swimming, shelling, build sandcastles, and enjoy the ocean with a bit more privacy.
Midnight Pass Road provides the only (easy to miss) public access to enter Crescent Beach, and from there, there’s a 25-space parking lot and walking pathway that leads out onto the beach.
Bonus: At the south end of Crescent beach you’ll find one of Siesta Key’s hidden gems: Point of Rocks.
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.
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 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.
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.
Siesta Key Itinerary: Day 5
- Get coffee and crepes at Bonjour’ French Cafe.
- Take a 2.5-hour Dolphin, Drinks, and SandbarTour from Siesta Key Watersports.
- Drive 15 miles South to visit the “Shark Tooth Capital of the World”, Venice Beach, Florida.
- Shop through downtown Venice and spend time at Venice Beach and the Venice Beach Pier.
- End your day with dinner and drinks at Sharky’s on the Pier.
Day 5: Siesta Key Itinerary
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 taking an unforgettable guided dolphin cruise!
Finish the day by visiting nearby Venice Beach, Florida!
Siesta Key Dolphin Cruise
Another fun thing to do in Siesta Key is to watch dolphins jump and play in their natural environment on a guided dolphin cruise!
With Siesta Key being home to one of the largest populations of wild bottle-nose dolphins, you’re likely to see not one – but multiple – dolphins jumping and playing in the water!
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. We loved both the Dolphins, Drinks, and Sandbar tour and Sunset Dolphin Cruise with Siesta Key Watersports!
Venice Beach
Located only 15 miles from Siesta Key, we totally recommend squeezing in a visit to Venice Beach during your Siesta Key itinerary!
Known as the “Shark Tooth Capital of the World”, Venice Beach in Venice ,Florida, 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 that can be found between the months of May and October.
Not only that, but you’ll also want to check out the 700-foot long Venice Fishing Pier and have dinner at the tourist hot spot, Sharky’s on the Pier afterward!
Sharky’s is located oceanfront, 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 – plus, they do take reservations!
Siesta Key Itinerary: Day 6
- Drive 7 miles North to Sarasota, Florida.
- Stop to take photos at the Unconditional Surrender Sculpture.
- Visit the the Marie Selby Botanical Gardens and/or the Circus Museum at The Ringling.
- Check out Lido Beach.
- Browse, shop, and dine at Lido Key’s St. Armands Circle.
- Have dinner at Cafe’ on St. Armands before you head back to Siesta Key.
Day 6: Siesta Key Itinerary
To cap off your amazing Siesta Key family vacation, venture out to nearby Sarasota, FL, and/or Ana Maria Island, if you have time.
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, Ringling Museum, and Marie Selby Botanical Gardens, as well as visiting its popular shopping district, St. Armand’s Circle.
With so much to do in Sarasota, you can spend several days there and still find things to do.
For that reason, we’ve included our 6-day Saraosta vacation itinerary here if you’re looking for more ideas on how to plan your time there.
Another option, or something you could do on a different day or a different time visiting this area, is to travel 26 miles to Ana Maria Island.
Though 26 miles seems close, plan on plenty of time (like a full day trip) for this option however, as the slow, island driving conditions makes the trip to and from Ana Maria Island last a minimum of 1 hour each way.
We’ve written about all of the best things to do on Ana Maria Island, here!
More Info on How to Get Around Siesta Key
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 offers free round-trip service from Siesta Key Village to the southernmost part of the island, with many stops along the way. (Effective November 2024 Route 77 also connects riders to Downtown Sarasota.)
Likewise, Jonny’s Original Free Beach Rides, and Siesta Key Frog Hop also offer, free and convenient transportation throughout Siesta Key.
Also, though these options are all free to ride, they all greatly appreciative and rely on tips.
Suggested tip amount is $3 to $5 per person.
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.
Be sure to check out our related posts before your trip:
*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*
This is HIGH on my must-go to list. I’ve heard its incredible! Not far from my parents either. When travel opens up again!
Yay, sounds awesome! We plan to go there again next March as well!!
We love Siesta Key and this is a great itinerary for a beach trip there!
Thanks Amanda! It is a fabulous family-friendly destination!
Incredible beach, so much to do and wonderful suggestions for planning a terrific getaway. Now we just need to be able to getaway….!
Oh, I know (sigh!)…I dream of the day we can all begin traveling again!! 🙂
Wow! This beach looks gorgeous! I love fully detailed itineraries because everything has already been planned for you!
Yes! I absolutely love making itineraries for people, in fact, that is why I started blogging in the first place (because my friends would always ask me for my itineraries 🙂
Siesta Key looks like such a great place to visit…I might even get up for sunrise with views like that! 😍
I tell ya what…I LOVE the gulf of Mexico! The water and the skies are absolutely incredible!