Naples Weekend Itinerary
Friday: Arrival & Downtown Old Naples
- Afternoon: Check into your resort and stretch your legs with a walk down Fifth Avenue South or Third Street South. These parallel historic avenues are the epicenter of Old Naples, packed with upscale fashion boutiques, coastal art galleries, and lushly landscaped walkways.
- Evening: Enjoy a romantic dinner at Mediterrano, a highly-rated upscale Mediterranean spot. Afterward, catch a legendary Gulf sunset at nearby Lowdermilk Park.
Saturday: Secret Beaches & Vibrant Nightlife
- Morning: Beat the crowds to Clam Pass Park. Take a free, scenic tram ride across a three-quarter-mile boardwalk winding through a dense mangrove forest. Once at the beach, jump into the narrow pass at the edge of the mangroves to enjoy a natural "lazy river" tide ride that safely sweeps you inland or out to the Gulf, depending on the tide.
- Lunch: Head up to Vanderbilt Beach and experience waterfront dining at The Turtle Club Restaurant, widely considered one of the best spots to eat with your toes directly in the sand (Note: reservations are highly recommended months in advance).
- Afternoon: Indulge in some high-end retail therapy at the open-air Waterside Shops, home to luxury houses like Gucci, Hermès, and Louis Vuitton. Alternatively, browse the historic waterfront boardwalk at Tin City, a collection of local antique and novelty shops built inside 1920s clam-shelling buildings.
- Night: Spend your evening at Mercato in North Naples. This lively complex operates like a "city-within-a-city," allowing you to seamlessly walk between upscale dining, craft cocktail lounges (like Bar Tulia), and live entertainment.
Sunday: Eco-Adventures & Waterfront Brunch
- Morning: Start early with a trip to the Corkscrew Swamp Sanctuary. Walk the 2.25-mile elevated boardwalk through the world's largest remaining virgin bald cypress forest. Keep an eye out for alligators, white-tailed deer, and rare bird species. If you prefer the water, look into booking a morning guided mangrove kayak or paddleboarding tour through the local bays.
- Brunch: Cap off the weekend with an elegant waterfront Sunday brunch at BALEEN Naples, located at the LaPlaya Beach Resort, offering sweeping views of the turquoise ocean.
