Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Naples is known for
Naples is known for its Gulf of Mexico beaches, the historic Naples Pier, and Fifth Avenue South, the downtown street that has served as the town's unofficial Main Street since the 1920s. It is also the gateway to the Western Everglades, with Big Cypress, Everglades National Park and Corkscrew Swamp all within about an hour.
The first Naples Pier was built in 1888 and has been rebuilt after hurricanes in 1910, 1926, 1944 and 1960, and again after Hurricane Ian in 2022. Ed Frank's Garage became the first commercial building on Fifth Avenue South in 1923, and the Orange Blossom Special train first reached the Naples depot on January 7, 1927. Naples became an official city in 1949. Downtown Naples mixes seasonal visitors and full-time residents who walk to the beach, dine on Fifth Avenue and shop Third Street South. North of downtown, gated and association communities like Pelican Bay and Park Shore offer high-rise condos and private beach clubs.
Where to live
The historic core around Third Street South, two blocks from the Naples Pier and the Gulf. Beach cottages and residential architecture sit inside the Naples Historic District, which is listed on the National Register of Historic Places. (source)
Waterfront neighborhood between Port Royal and Old Naples. Deep-water channels and coves give many homes boat access to the Gulf, and development here began in 1949. Walking distance to the beach, Third Street and Fifth Avenue. (source)
Waterfront neighborhood at the southern end of the city off Gordon Drive. Property ownership here is tied to eligibility for the members-only Port Royal Club beach club. (source)
Gulf-front neighborhood with high-rise condominiums, single-family homes and low-rise residences. Venetian Village sits at its center, and the Park Shore Association runs a private beach park for members. (source)
Master-planned community of more than three square miles, renamed from Clam Bay in 1974 and developed by WCI. The Pelican Bay Foundation runs nearly 3 miles of member beaches, beachfront restaurants, a tram, racquets facilities and design review covenants. (source)
Local favorites
A Naples fixture for nearly 30 years, known for USDA Prime and dry-aged steaks, seafood and hand-crafted sushi. Locals book it for milestone celebrations. (source)
Billed as Naples' first osteria, with Chef Vincenzo's cucina rustica served lunch and dinner in a restored Italian farmhouse setting. (source)
A local favorite for fifteen years, now in a new Fifth Avenue location with Persian cuisine and a lush dining room. (source)
Steps from the beach, with dinner nightly, a weekend brunch with set seatings, and a 75-seat outdoor patio. (source)
Classic Fifth Avenue spot with Mediterranean dishes, a strong Italian emphasis and open-air dining. (source)
Relaxed spot for fresh seafood, tropical flavors and cocktails, open daily for lunch, happy hour, weekend brunch and dinner. (source)
All-day Roman-style bakery led by Italian Pastry Chef Marco Berardi, open daily from 7:30am to 10:30pm. (source)
Locally owned sister to Caffe Milano, open late (until 1am Tuesday to Sunday) with craft cocktails. (source)
After hours
12.84-acre downtown park just south of Fifth Avenue South with a bandshell for concerts and outdoor movies, the Arthur L. Allen Tennis Center, shuffleboard, bocce and the Norris Community Center. The playground is closed for renovation. (source)
City beach park with sand volleyball courts, a playground, picnic gazebos, ADA beach mats and the Flip Flop Beach Grill concession. Beach parking needs a permit or pay-by-space. (source)
Old Naples district of courtyards, fountains, chef-owned bistros and brunch spots, with a seasonal farmers market and events like Christmas on Third and Pets on Third. (source)
Movie theater inside the Mercato mixed-use center, which also runs seasonal events like a pumpkin patch and a music series. North Naples. (source)
Art center at 585 Park Street with exhibitions, adult and youth classes and workshops, and the Scene To Be Seen wearable art runway fundraiser. (source)
Shopping
Downtown's main street for apparel, fine jewelry, art galleries, home furnishings and more than 30 restaurants, with valet and garage parking. (source)
Open-air luxury center at 5415 Tamiami Trail North with stores such as Tory Burch, Lilly Pulitzer and Vuori. North Naples. (source)
More than 45 shops and waterside restaurants set on Venetian Bay in Park Shore. (source)
Mixed-use center at 9110 Strada Place with shops, restaurants, offices and a Drafthouse Cinema. North Naples. (source)
Outdoors
15-acre park on the Gordon River that opened in 2019, with a kayak launch, boat dock, a 1.3-mile looped trail, playgrounds, a splash pad and an outdoor fitness area. (source)
Nearest state park, a barrier island beach in North Naples with swimming, shelling, paddling in Water Turkey Bay and the Cocohatchee River, and birding. $6 per vehicle. Maintenance dredging of Wiggins Pass began September 25, 2026, with periodic parking lot closures. (source)
Mangrove estuary with boat eco-tours, kayak tours and rentals, trails and an Environmental Learning Center. The learning center reopens October 1 and the Briggs Boardwalk is closed for renovation. (source)
Audubon sanctuary with a boardwalk through the Western Everglades and a Ramsar Wetland of International Importance. Open 8am to 1pm May through mid-December, 8am to 3pm mid-December through April. Rural Naples (34120). (source)
Federal refuge protecting mangrove, marsh and tropical hardwood hammock habitats along the southern Collier coast. (source)
Over 729,000 acres of cypress swamp and habitat for the endangered Florida panther, with wet hikes and trails. Headquarters in Ochopee on Tamiami Trail East. (source)
1.5 million acres of wetland, forest and marine habitat. The Gulf Coast side of the park is reached through Everglades City. (source)
Things to do
Zoo set in a historic botanical garden with giraffes, lions, a Malayan tiger, a Florida panther and a Primate Expedition Cruise. (source)
Garden at 4820 Bayshore Drive with 90 acres of natural areas, tram tours, Fogg Cafe and children's nature play. Adult tickets are $27 and children 17 and under are free. (source)
Automotive museum at 2500 Horseshoe Drive South with more than 120 historically significant road-ready cars in an 80,000-square-foot space. Closed each August 2 through September 30 for maintenance. (source)
Accredited fine art museum focused on modern and contemporary art, on the same campus as the Naples Philharmonic. (source)
Restored Seaboard Air Line passenger station at 1051 Fifth Avenue South, listed on the National Register of Historic Places, with Seminole dugout canoes, antique swamp buggies and rail cars. Open Tuesday to Saturday. (source)
On the calendar
Charity wine, food and auction weekend at The Ritz-Carlton Naples, Tiburon, benefiting Collier County children through the Naples Children Foundation. (source)
Old Florida tradition of racing swamp buggies, with a Swamp Buggy Parade on race weekend. (source)
Annual tree lighting and dining night on Fifth Avenue South, part of a holiday lineup that includes a Christmas parade and Tuba Christmas. (source)
Outdoor fairs with original work by local, national and international artists. (source)
Recurring evening event series on Fifth Avenue South. (source)
Schools
Lake Park Elementary School, Sea Gate Elementary School
Gulfview Middle School, Pine Ridge Middle School
Naples High School, Barron Collier High School
Community School of Naples, Seacrest Country Day School
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
US-41 (Tamiami Trail), I-75, Goodlette-Frank Road, Gulf Shore Boulevard
Southwest Florida International Airport (RSW) in Fort Myers, about 36 miles and roughly 50 minutes by road. Naples Airport (APF) is a general aviation airport about 4 miles from downtown with no commercial airline service.
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.