The Sarasota Edit: A Curated 4-Day Itinerary for Coastal Families Who Love to Explore

Morning: Southern-inspired breakfast in the Village

Start your day with a relaxed, flavorful breakfast at Another Broken Egg Café, right in the heart of Siesta Key Village. Known for its Southern-style brunch favorites and cozy energy, it’s perfect for both early risers and those easing into island time. They are serving waffles, benedicts, cinnamon roll French toast, and spiked coffee (for the grown-ups). My favorites are the Crab Cake Eggs Benedict and South of the Border Spiked Coffee—just the right touch of vacation indulgence.

Midday: Shelling, sandwiches, & laid-back beach time

After breakfast, head down to Turtle Beach, a quieter stretch of shoreline on the island’s southern end. It’s ideal for families—with calm waves, shady picnic areas, and a playground for younger kids. This beach is also one of the best spots for shelling, so bring a bucket and make it a scavenger hunt. Note that this beach does not have the fine white sand that makes Siesta Beach famous. If this is what you are looking for, stick to the main beaches. If you are parking, I recommend Public Beach access #5 or #7 but spots fill up early.

Quick stop: On your way to Turtle Beach, swing by Anna’s Deli to pack the perfect beach picnic. Their signature “Surfer” sandwich is a local legend, but I always go for the chicken salad with cucumbers—fresh and beach-ready.

Afternoon: Village strolling & local finds

After a relaxing beach break, head back toward Siesta Key Village to explore its boutique shops and beachy charm. Stop into Beach Bazaar for family-friendly gear and souvenirs, or browse Siesta Key Outfitters for custom tees. You’ll also find familiar favorites like Lilly Pulitzer and Tommy Bahama.

Visiting on a Sunday? Pop into the Siesta Key Farmers Market—it’s small but full of coastal character, local treats, artisan goods, and hand-crafted Siesta Key Rum that makes a great take-home gift.

Late afternoon: Snacks, sip, & live music

Ease into the evening with a happy hour stop at The Hub Baja Grill, where fresh grouper tacos, signature margaritas, and live music set the tone for a fun, casual break. Their covered patio is shaded and breezy—great for people-watching or letting kids recharge while adults enjoy a sip and snack.

Still thirsty? Step across the street to Am I Coconuts, serving up fresh coconut concoctions all alcohol-free and kid-friendly. This is a perfectly Instagrammable stop to your Siesta Key day!

Evening: Dinner & sunset by the sea

For dinner, head just down the street to The Cottage, their outdoor seating is perfect for warm evenings and their menu caters well to both adventurous eaters and picky kids.

Then, walk over to Sunset Point to catch the sun sinking while the kids run out their remaining energy.

Final treat: Mini donuts to go

Before calling it a night, stop at Meaney’s Mini Donuts in the Village. Warm, cinnamon-dusted donuts made to order are the perfect sweet ending to a Siesta Key day done right.

Staying on Siesta Key? Most families opt to rent a house or condo. There are several rental homes that can accommodate large, or multi-gen families. I can help you find the perfect fit.

A well-rounded Sarasota day that blends hands-on fun for the kids with culture, great food, and a little downtown charm.

Morning: Coffee & light bites at Project Coffee

Start the day at this modern, welcoming café. Strong espresso, clean ingredients, and cozy seating make it a great choice whether your crew is easing into the day or grabbing something on the go. Try the avocado toast or a berry bowl, and don’t skip their house-made pastries.

Mid-morning: Sarasota Jungle Gardens

Just 10 minutes away, Sarasota Jungle Gardens is a classic for a reason. Hand-feed the flamingos, watch a wildlife show, and enjoy the shaded tropical trails. Enjoy a morning of old-Florida charm and local wildlife.

Lunch: The Wicked Cantina (on Tamiami Trail)

This local favorite brings a relaxed, colorful vibe and family-friendly menu. Great for tacos, burgers, and burrito bowls. Parents will appreciate the margaritas; kids will love the chips and cheese, and laid-back patio. Of course, my kid always orders the market-price grouper sandwich (ouch!), but they have several kids’ options and a diverse menu that definitely brings the Tex to the Mex. Don’t skip the queso.

Afternoon: The Ringling Museum

Spend your afternoon exploring one of Sarasota’s cultural treasures.

Start with the Circus Museum for a fun and interactive look at the region’s performance history.Then head into the art galleries and sculpture gardens.The bayfront Ca’ d’Zan mansion makes a beautiful walk for grown-ups while kids run out their energy on the lawn.

Bonus: On Thursday evenings, enjoy Ringling Family Nights—discounted admission after 5 pm with themed activities and pop-ups designed for families.

Dinner: Downtown Sarasota favorites

Head back into the heart of Sarasota for a variety of upscale-but-approachable dinner options. Here are a few favorites depending on your family’s mood:

• Hyde Park Steakhouse: Classic steakhouse experience.

• Carragiulos: Italian-American comfort food.

• Selva Grill: Latin fusion with creative small plates.

• Owen’s Fish Camp: Laid-back seafood with local flavor.

• Jack Dusty: Waterfront views and standout Sarasota Cioppino.

Dessert: Great Heights Creamery

Wrap up the day with small-batch, inventive ice cream in a relaxed, open-air backyard-style space. Cornhole, ping-pong, and space to roam make this stop a family favorite.

Try the “Yes, Honey” — a local artisan flavor made with Sarasota raw honey.

Today is all about getting on the water—up close with the natural beauty of Sarasota Bay, local marine life, and a taste of island adventure your whole family will remember.

Morning: Breakfast at Blue Dolphin Café (St. Armand’s Circle)

Fuel up at this local favorite among the shops of St. Armand's. Blue Dolphin Café serves a no-frills but flavorful breakfast—classic pancakes, eggs, and toast with quick service and casual charm. Perfect for early-risers and families ready to hit the water.

Late morning: Mangrove Tunnel kayak tour at Ted Sperling Park

Head over to Ted Sperling Nature Park for a guided kayak tour through the mangrove tunnels. The calm, shallow waters make it an ideal paddle for beginners and kids, with opportunities to spot dolphins, manatees, and coastal birds along the way. It’s an active adventure that still feels peaceful and scenic. Tours usually last 1.5–2 hours; I can book you ahead for best times.

Lunch: New Pass Grill & Bait Shop

Head to New Pass Grill, a casual dockside spot with Old Florida charm and unbeatable water views. Perfect for a sweaty lunch after your kayak tour. It’s known for juicy burgers, hot dogs, fried shrimp baskets, and cold beer. While you eat, the kids can watch fishing boats come and go—or say hi to the pelicans from a high-top bar or a shaded picnic table. Nothing fancy here, just low-key, local, and always a hit.

Afternoon: Sea Life Encounter Cruise with Sarasota Bay Explorers

Board this hands-on marine education cruise departing from Mote Marine Laboratory. This family-friendly tour includes a marine life touch tank, dolphin and seabird spotting, and even a stop on an uninhabited island for shelling and tidepool exploration. A must-do for curious kids and nature-loving grown-ups alike. Tours are two hours long—reservations required.

Dinner in St. Armand's Circle

End the day back in St. Armand's with an easygoing dinner that suits every family member’s taste. A few favorite picks:

• Columbia Restaurant: Classic Spanish-Cuban cuisine. Try the iconic 1905 Salad and sangria.

• Blu Kouzina: Fresh, authentic Greek fare with many ingredients flown in directly from Greece.

• Venezia: A family-friendly Italian trattoria with upscale pizzas, house-made pastas, and gelato to go.

Today’s about breezy freedom on the water—no strict schedule, just sun, sea, and unforgettable family time.

Morning: Quick breakfast & boat snacks at Publix, Longboat Key

Before heading out, swing by Publix on Longboat Key for a quick breakfast and some on-the-water essentials. Think muffins, fresh fruit, and plenty of cold drinks. Stock up—you’ll want something easy for snacking while cruising.

Boat rental from Cannons Marina

Pick up your rental at Cannons Marina, where the team will walk you through the best routes, secret sandbars, and local fishing tips. Their fleet is clean, well-kept, and perfect for families—whether you want to cast a line, spot dolphins, or just relax and explore. Be sure to reserve your boat in advance—this is a popular activity, especially on weekends. If you prefer a guided trip, ask me about the best local captains.

Midday: Dock for lunch at Mar Vista or Shore

Just across the bay, pull into the dock and choose between two of our favorite boat-up lunch spots:

• Mar Vista Dockside: Sit with your toes in the sand under the shade of ancient trees while the kids splash nearby.

• Shore: A stylish, open-air patio with coastal-chic vibes, refreshing cocktails, and great seafood.

Both offer easy docking and relaxed, family-friendly menus. You really can’t go wrong.

Afternoon: Anchor at Jewfish Key Sandbar

Spend your afternoon anchored at Jewfish Key Sandbar, a stunning stretch of shallow, clear water perfect for wading, floating, or exploring. This is a local favorite for good reason—it feels like your own slice of paradise. Anchor near the shore side (not too close to the bridge) for the safest, calmest experience.

Don’t forget: floats, snorkels, sunscreen, and waterproof phone cases for a camera roll full of memories.

Dinner: Casual, lingering dinner at Whitney’s

Kick back with a fresh fish taco and a frozé at Whitney’s on Longboat Key. It’s stylish yet unfussy—an ideal sunset setting to toast a perfect day on the water. Bonus: the laid-back outdoor seating means the kids can still roam a bit while you linger..