Few destinations match the charm of Florida. From its perfect year-round weather to its immaculate beaches and robust culinary scene, The Sunshine State has all the ingredients for a riveting getaway experience. If you’ve been contemplating a relaxing vacation to this gorgeous state, look to the beautiful barrier island of Siesta Key. This scenic destination is a holiday hotspot, drawing around 2.2 million annual visitors thanks to its impressive collection of attractions. Here’s an exciting three-day itinerary for the ideal Siesta Key fall vacation.
Day 1: Hit the Beach
Siesta Key is home to some of the state’s most picturesque beaches, perfect for a fun-filled day by the water’s edge. Siesta Beach is arguably the island’s most beautiful, consistently ranking among the US’s top beaches. Its white, soft, powdery sand creates a cozy setting for a relaxing experience as you relish the cool Gulf breeze. The waters in Siesta Beach are calm, making it a safe spot for swimming and other on-water activities. The beach stretches over a mile, offering plenty of sand to soak up the sweet rays of sunshine. Enjoy access to tennis courts, volleyball courts, a picnic area, and a shaded playground for the little ones. Several lifeguard towers in strategic locations ensure a safe experience in the water. Two concession stands offer delightful treats and refreshing drinks for much-needed energy to keep you going.
Turtle Beach is another Siesta Key favorite, offering a more secluded Gulfside experience. The beach features half a mile of beachfront, giving easy access to the warm waters of the Mexican Gulf for a soothing swim. Turtle Beach’s black and white sand gives it a unique look, although its coves and moderately steep descent to the water’s edge make it a bit tricky to walk during high tide. If you’re looking for a spot to test your angling skills, Turtle Beach offers a boat launch and fishing expeditions on the nearby Blind Pass Lagoon. Plan a low-tide stroll along the dark sands, and you may find several choice shells or the odd shark’s tooth to collect as a souvenir. The area features nearby eateries and shopping centers for food and drinks or beach attire.
Sarasota Beach lies on the island’s northern part, offering a scenic trail lined with natural vegetation cover, including cabbage palms and sea oats. The beachside homes sit far from the beachfront, offering more space to set up your beach gear. Settle down by the water’s edge and enjoy the gorgeous views of the Gulf. The expansive white sands offer easy access to on-water activities, including kayaking, swimming, and surfing.
Day 2: Explore the Culinary Scene
After your seaside escapades, plan a day exploring Siesta Key’s vibrant culinary scene and treat your taste buds to some of Florida’s finest cuisine. Start your day with a hearty breakfast at Sun Garden Cafe and sample some of their delightful pastries, which include Cinnamon Sticky Buns, Gooey Butter Cake, or Sol Muffins. If baked goods aren’t up your alley, try the Fresh Seasonal Fruit Bowl, Charleston Grits, or Organic Gluten-Free Granola. Enjoy seven sandwich and bagel options, including Crescent Beach Croissant, Ziggy Stardust, Feynman’s Answer, and Bronx Bagel. Add protein to your breakfast by ordering one of eight omelet options, including Andy’s Ways, Flower Child, Birkenstocker, or Kitchen Sink, where you create your custom omelet.
After your morning meal, schedule a delightful lunch at The Cottage and relish an outdoor dining experience on their patios. Start with something light and choose from a Patio Salad, Cottage Caesar, or Superfood Salad. Add your preferred protein choice to any salad, including shrimp, tuna poke, salmon, chicken, or marinated tofu. Keep things light with one of the tapas options, which include Cottage Crab Cake, Shirt Rib Bites, Scallop Tiradito, Grilled Shrimp Causa, Calamari Fritti, or Peruvian Ceviche. The entrees feature eight savory dishes, including Beef Short Ribs, Filet Mignon, Roasted Peruvian Chicken, and Siesta Seafood Scampi.
End the day with a lovely dinner at The Hub Baja Grill on Ocean Boulevard. Start your evening with one of their starters, including Hub Wings, Chips & Salsa, Grouper Bites, or Grande Nachos. The salad options include Siesta Key Salad, Baja Salad, and Tijuana Cobb Salad with your choice of chicken, shrimp, mahi, or grilled grouper. The Hub Cuban, The Baja Burger, the Grouper Sandwich, and the Baja Nights Chicken Sandwich form a delightful sandwich list. Some local fresh favorites include Fajita Sampler and Baby Back Ribs.
Day 3: Traverse the Biking Trails This Fall in Siesta Key
Prepare for a final day of thrilling bike rides along Siesta Key’s numerous biking trails and relish the island’s beauty. If you prefer a short biking experience, hit the Bayshore Trail and enjoy the paved 0.9-mile route. The tarmacked section lies along the eastern side of Clearwater and runs parallel to Bayshore Boulevard. Most of the trail runs through beautiful tree-lined neighborhoods, offering a scenic biking excursion. If you need any repairs, there’s a bike repair spot on the corner of Bayshore Boulevard and FL-60 across from the Courtney Campbell Causeway Trail.
The Clearwater Memorial Causeway Trail features a 3.5-mile asphalt route connecting Pinellas Trail to Clearwater Beach via the Memorial Causeway. The trail runs close to the water most of the way before entering Clearwater Beach. Numerous overlooks along the way allow you to stop and relish the picturesque views of the bay.
Courtney Campbell Trail has a mix of asphalt and concrete surfaces, running 10.5 miles along the Courtney Campbell Causeway’s southern side. The route offers breathtaking views of Tampa Bay and links Cypress Point Park to Skyway Park and Ben T. Davis Beach. The pathway runs parallel to the highway, offering easy connections to the Wilson Clearwater Trail and the Druid Road Trail.
If interested in an extended biking experience, check out the Legacy Trail and enjoy an 18.5-mile bike ride along the smooth asphalt surface. The route runs adjacent to the coast between Venice and Sarasota, offering picturesque views of the Gulf. After four miles, the trail passes by the Historic Venice Train Depot, a perfect spot for snapping a picture or two. The pathway offers a level and straight biking 12-mile journey from Bahia Vista Street, with the only incline at the US 41 pedestrian overpass. The trailhead by the bronze statue of Gunther Gebel-Williams offers restrooms and drinking water for freshening up this fall in Siesta Key.
Book Your Siesta Key Fall Vacation Rental Today
Siesta Key is one of Florida’s foremost holiday spots loved by millions. This lovely barrier island lies adjacent to the majestic Gulf, offering vacationers a unique holiday experience. As you plan your relaxing getaway to this beautiful Florida gem, look to Rent Siesta Key for the best vacation rentals on the island. We offer an impressive variety of holiday homes, including beach-view properties, on-the-beach rentals, condominiums, rentals with hot tubs, homes with pools, and pet-friendly houses for the ultimate getaway for a Siesta Key fall vacation and beyond. We have over 15 years of experience in the vacation rental space, delivering quality lodging for over 50,000 guests. Skip the hassle of booking, processing, and administration fees and enjoy the most competitive rates on the island. Contact us today to secure your Siesta Key vacation rental and experience a Florida getaway like no other.
