A neighborhood comprising about 550 palatial homes, this is one of the most prestigious places to live not just in Florida, but in the United States. Named after the infamous Jamaican pirate port and nestled between the Gulf and Naples Bay at the southern end of the city, it hosts rows of ornate estates on streets with names—Spyglass Lane, Rum Row and Man of War Cove—inspired by the local pirates who once used the area as a stopover. Drive through and gawk at the magnificent homes. One sold for $30 million several years ago and many have impressive yachts bobbing in the deep canals out back.
One of the area’s attractions is the contrast of tony high-end resorts and mansions only a few miles from the primal Everglades and the 10,000 Islands—a chain of mangrove islets stretching south from Marco Island to Flamingo on the tip of the peninsula. Narrated airboat rides, kayak tours, fishing trips and guided swamp walks are examples of what you can do here, getting back to nature at its most basic level. Midday, stop for a seafood lunch at one of the many eateries, and if you really fall in love with the rustic experience, spend a night at the Ivey House Bed and Breakfast.
Boats and fishing are big in this little spot around and on Naples Bay—they call it an “old salt’s delight.” But you needn’t be an old salt to appreciate the maritime-themed shops and restaurants. If you’re into fishing or sailing, this is the place to charter a boat. The Naples City Dock is home to the city’s largest fishing fleet. From here, you can walk to the more-upscale shops downtown on Fifth Avenue and Third Street South if you like, or the Naples Trolley provides service from the marina throughout the city.
Fifteen miles from downtown Naples, this quiet little community is where art meets the ocean. The barrier island is the largest and most northern of the 10,000 Islands, sort of like the dot on an upside down exclamation point. Although it’s heavily developed—paved end to end with waterfront residences and resorts—it still has pristine beaches. The natural beauty and the laid-back lifestyle have help attract the more than 100 art galleries that populate greater Naples. The coastal estuaries and shallow passages that weave between the islands are popular cruising grounds that offer a very different seascape from the rest of South Florida. Dolphins are routinely spotted, and you’re likely to see bald eagles and osprey out looking for fish to swoop up. Not surprisingly, fishing is big business, with charters to both the inshore shallows (for reds, snook and tarpon) and deeper water offshore for tuna and wahoo. Hardcore sea kayakers like the area because it’s never a very long pull to the next island, some of which are suitable for camping; however, in the summer, heat and the lack of available fresh water can make it dangerous for the inexperienced. Guided day trips are popular with casual kayakers and canoeists and they’re a great way to see the rich mangrove shallows that line the bays. There are boardwalks and a butterfly garden at Marco’s Tigertail Beach, which has full facilities (including grills) if you want to stay all day and barbecue.
There’s a The Great Gatsby retro feel to this walking district, with its Mediterranean-style buildings in pastel colors with green awnings and meticulously manicured hedges and palms. You can spend the good part of a day or evening here, perusing the stores and art galleries, sitting street side with a coffee or gelato, taking in the sights, enjoying live music or just passing hours over a gourmet dinner with friends and good wine.