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Day One · May 22
Depart Miami at 4:00 PM; arrive Naples by 6:15 PM. Check into your hotel, then head directly to The Bay House (850 Naples Bay Drive) for sunset dinner. This waterfront gem sources daily from local fishermen and farms, serving pristine grouper crudo and wood-fired vegetables that showcase Southwest Florida's agricultural bounty. Sit on the dock to watch the sun ignite the bay—reserve a table beforehand.
Day Two · May 23
Start at Naples Pier at Sunrise (12th Avenue South, at the beach). Arrive by 7:00 AM for a 90-minute guided shelling walk with a local naturalist (book via Naples Beach Hotel concierge the night before). You'll collect lightning whelks and fighting conchs while learning estuary ecology. Post-walk, grab cold-pressed juices and açai at Keto Karma (3833 Tamiami Trail N)—their smoothie bowls use local coconut and organic berries.
Rent a Turo car (essential for this leg). Drive 45 minutes to Corkscrew Swamp Sanctuary (375 Sanctuary Road, Estero). Hike the 2.25-mile boardwalk through old-growth cypress forest and alligator habitat—a cathedral of Florida wilderness inaccessible without a car. Return to Naples by 4:00 PM. Shower at your hotel, then visit Third Street South Gallery District for art browsing and a light early dinner at USS Nemo (239 Third Street S). Order their wood-grilled fish with charred seasonal vegetables and heritage grains—the kitchen's ethos is "one ingredient, one way." The intimate dining room buzzes with local energy.
Walk to nearby The Von Liebig Art Center for their Friday night art openings (check schedule), or enjoy cocktails and live jazz at The Dock at Crayton Cove (12th Avenue S, waterfront)—order their smoke-free botanical cocktails and wood-fired oysters while overlooking the marina.
Day Three · May 24
Book a dawn kayak eco-tour through Naples Bay kayak (departs 8:00 AM from Naples Pier). Paddle through mangrove tunnels spotting dolphins, manatees, and roseate spoonbills. Return by 10:30 AM, then head to The Dock for brunch. Order their eggs Royale with smoked salmon from local fish and farm greens, plus fresh-squeezed OJ. Linger over coffee on the deck.
Leave Naples by noon. Take the scenic Tamiami Trail (US-41) back toward Miami rather than I-75—you'll hug the coast, pass through the Ten Thousand Islands viewpoint, and see Gulf sunlight on water the entire drive. Stop at Everglade City (20 minutes out) for a quick walk through this historic fishing village if departing later, or drive straight home by 2:15 PM.
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