Like many of Naples’ residents and visitors, Colin Estrem came to this Gulf-front town from the Midwest. The Wisconsin transplant moved here three years ago to join the area’s thriving restaurant scene, which has bloomed within the past decade. When he’s not tending to his new business—Avenue Wine Bar on Fifth Avenue downtown—Estrem enjoys fishing on the Gulf and dining alfresco at sidewalk cafés.
“Naples is the best of both worlds. I describe it as a cross between Orange County and a fishing village,” he says.
“I can go downtown and have a gourmet meal in a chic, cosmopolitan restaurant, and then, within minutes, I can be at the beach or out on the water.”
It is this duality of upscale amenities and natural assets that gives Naples its charm. In fact, the city’s popularity with folks from the Frozen North even has prompted some to call Naples the Riviera of the Midwest. And many of those visitors eventually become converts, moving to Naples as full-time residents. That’s the strength of its allure.
The heart of the city, Old Naples, comprises two bustling streets, Fifth Avenue South and Third Street South. Lined with palm trees, lush bougainvillea, and European-inspired architecture, these downtown areas offer top-notch shopping, dining and entertainment. Although Naples has become quite upscale with ongoing development, it is tempered by a laid-back, mellow vibe. This is Florida, after all, and many denizens operate on “island time” (meaning slow paced).
“The most amazing thing about living in Naples is that you can enjoy a really casual lifestyle—shorts and flip-flops are the uniform—and yet still be in a chic, upscale-feeling environment,” says Cathy Christopher, director of sales and marketing for the Inn on Fifth, a popular downtown hotel. “Somehow Naples has captured the magic of being elegant combined with casual, easy and unpretentious. It really is magic.”
Naples sunsets are also magic, as the sun sinks to the horizon over the Gulf, awash in a palette of warm colors. One of the best vantage points for this nightly show is the Naples Fishing Pier, built in 1888. This area landmark reaches out over the water from the sugar-white sand of the Municipal Beach, one of several beaches in the area. Other popular options include Vanderbilt Beach and Lowdermilk Beach Park, while Clams Pass Beach Park and Delnor Wiggins Pass State Recreation Area are a bit more private. They all offer opportunities for swimming, shelling, watersports and just general beach-bumming.
New York Times bestselling author Dr. Robin Cook, who has lived in Naples since 1981, thinks that the Gulf is the city’s No. 1 asset and spends his time swimming, body surfing and windsurfing.
“The main reason the city is there and the main reason I’m there is because of the proximity of the water,” he says. “I like to take advantage of the water every day.”
The Naples area is renowned for its saltwater fishing, and one of the best spots is the 35,000-acre Ten Thousand Islands National Wildlife Refuge, southeast of Naples. It’s open to the public for fishing, hunting, camping and wildlife viewing (manatees, alligators, dolphins, and other occupants).
Another natural attraction is the Audubon Corkscrew Swamp Sanctuary, northeast of Naples, where visitors traverse a 2.25-mile raised boardwalk through a pine upland, a wet prairie, a cypress forest, and a marsh. Expect to see a wide variety of birds, flowers, and butterflies—and maybe even a bobcat or a bald eagle. Pick up a pair of binoculars and a field guide from the Nature Store to prep for the trek.
Less adventurous visitors can enjoy the outdoors and the Florida sunshine in a more refined environment by hitting the links. Golf is a favorite pastime in Naples—as evidenced by the fact that it has the highest ratio of golf courses to golfers in the country. Try the Naples Beach Hotel & Golf Club for a retro modern vibe, or opt for the Ritz-Carlton Golf Resort for a more posh experience. After a day of fun under the sun, capped off with a first-rate dinner, it’s no wonder that some visitors never leave Naples.
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