You’ve heard about Naples, Florida, for years now. You’ve heard it’s Twin Cities South in winter; that every Twin Citian with second and third homes owns one here; that your doctor, financial advisor, and attorney all have satellite offices on Fifth Avenue; and that Minnesota business expats gather for breakfast by the beach every Friday to practice winter schadenfreude over eggs and oatmeal.
Familiar, yes, but why should you choose that for your escape from Minnesota? Don’t you want to get away?
I wasn’t seduced by Naples’s siren song until I spent time there this fall. Now I get it. Naples is different (from Florida, that is). It’s pedestrian scale, Midwestern friendly, and cultured. But it’s not Minnesota, and it’s hardly Florida 2.0–Naples loves its strip malls, vast commercial thoroughfares, and beachfront crowded with undistinguished high rises.
The two sides of Naples don’t intrude on one another. If you want your Capital Grille–Marriott–Dodge minivan–Lilly Pulitzer Florida vacation, you can get it in Naples. But if you want a mellow kind of Florida escape, where everything’s available on foot, from chic boutiques and soft sand to good restaurants and even a note of culture, you can have that, too (though a car still helps).
Naples reminds me a bit of Sarasota, a town that seemed to miss the ravages of the last three decades that blighted Florida with overdevelopment and kitsch. Naples is not as cultured as Sarasota, nor is the food scene as interesting, but it also lacks Sarasota’s poverty and vague patina of decay.
Naples is new. The town was barely inhabited throughout the first half of the 20th century; its big development boom occurred over the last 20 years. You won’t find much that’s historic or vintage because not much was here then. The railroad and US 41 both reached Naples around the Depression, and sprawling Fort Myers to the north absorbed much of the speculative development and chain blight that transformed Florida.
Naples is the antidote to all that, a difference you can especially feel on the Gulf side of downtown, in the old neighborhoods of cottages and plantation-style homes near the water. No vertical construction is allowed in Old Naples, so everything feels sedate, pre-Waffle House. Walk the streets between 10th and 14th Avenues near the Gulf, do the Naples Pier (less than a century ago visitors arrived primarily by boat), tour the historic Palm Cottage a block up 12th (it served as the municipal B&B for decades—until the 1960s, there was not even a large hotel, by Florida standards, here).
Still, Naples is not really a town of modest plantation-style cottages. Head north on Gulf Shore Boulevard to ogle a series of preposterous new-construction mansions. You’ll need a car (or bicycle). If you head south of town on Gordon Drive, you’ll end up in Port Royal, one of the largest communities of deluxe waterside residences imaginable.
Port Royal is not gated, though its windy streets can be confusing to navigate. Devotees of residential architecture will quickly be reminded that taste and money don’t go hand in hand. Most of the properties look a decade old or less, though one that escaped a teardown pops up occasionally. The predominant architectural style in Naples is what developers call “Tuscan.” Italy is not amused. The tiled roofs, conical entryways, brown stucco, and heavy wood shutters seem regrettable amid the green lawns, palms, and blue water.
Back in town, Third Street is Naples’s most attractive shopping and dining neighborhood—ground zero for strolling, people-watching, and boutique shopping. Fifth Avenue, traditionally the main drag of the downtown business and retail community, is also bustling and worth a look, but it lacks Third’s intimate scale and charm. (Avoid the tourist trap Tin City, which locals point you to out of a sense of spite, perhaps.)
If you’re looking for the heavy hitters, you’ll probably want to head to the Waterside Shops off US 41 and Pine Ridge Road, an open-air center with Nordstrom and Saks bracketing a large collection of luxury national brands, all surrounded by fountains and water features. It’s very nice, if not very local.
Practically next door is the Naples Museum of Art (5833 Pelican Bay Blvd., thephil.org), boasting a small but substantial modern permanent collection and interesting changing exhibitions, including Edgar Degas and Louise Nevelson in the current season.
Off the beaten path are two stellar natural areas. The Naples Botanical Garden (4820 Bayshore Dr., naplesgarden.org) southeast of downtown incorporates floral features from regions between the equator and 27 degrees latitude, where Naples is located. It’s a beautifully peaceful way to spend an afternoon. On the north side of town, the Corkscrew Swamp Sanctuary (375 Sanctuary Rd. W., corkscrewsanctuary.org), managed by the National Audubon Society, protects some of the largest remaining stands of native bald cypress trees and a plethora of rare birds in an environment typical of south Florida before so much of the swampy interior was drained for development. The self-guided walking tour is highly recommended.
One of Naples’s ironies is that its best hotels/resorts are well away from the center of town, particularly the waterside properties. The city’s grande dame is the beachfront Ritz-Carlton Naples (280 Vanderbilt Beach Rd., ritzcarlton.com/naples), a true showpiece resort boasting gracious service and traditionally formal Ritz ambiance and amenities, serving everyone from families to business travelers. It is prodigiously expensive, even off-season, but for true Naples devotees, it is the only game in town. Just down the beach is LaPlaya Resort (9891 Gulf Shore Dr., laplayaresort.com), a small 1960s tower with a smidgen of beach reborn into a gracious boutique hotel (ranked No. 12 in the United States by Condé Nast Traveler readers) with a warm staff, beautifully landscaped pool complex (nicer than the Ritz’s), and lovely water-view rooms.
The Ritz was so overwhelmed with demand that it built a golf resort a couple miles inland of its Naples flagship that boasts a lodge-like air, rooms with less formality but most of the intangibles you’d expect, plus shuttle service to the beachfront Ritz and all its amenities. The Ritz-Carlton Golf Resort (2600 Tiburón Dr., ritzcarlton.com/naplesgolf) offers value-rich off-season deals, though some facilities and services are high season only.
Most Twin Cities leisure visitors want a resort environment, but if you prefer to spend your vacation budget on shops and nightlife, downtown’s Inn on Fifth (699 5th Ave. S., innonfifth.com) and Bellasera (221 S. 9th St., bellaseranaples.com) come recommended by locals.
The Naples culinary scene is not modern or edgy and won’t wow those who winter in Sarasota, Miami, or Palm Beach, but there are some good choices. They begin with any of the restaurants from D’Amico & Partners, which established a beachhead in Naples in the 1990s. Campiello (1177 S. 3rd St., campiello.damico.com), Lurcat (494 5th Ave. S., cafelurcat.com), and D’Amico & Sons (4691 N. 9th St., damicoandsons.com) are all among the best options within their categories, and you may run into Naples resident Richard D’Amico. Other spots I can endorse: Baleen, the innovative global-fare restaurant at LaPlaya Resort (see Hotels); Jimmy P’s (1833 Tamiami Trail N., jimmypsbutchershop.com), a local butcher shop with killer sandwiches and burgers; Sea Salt (1186 S. 3rd St., seasaltnaples.com), probably the town’s best seafood restaurant; Truluck’s (698 4th Ave. S., trulucks.com) for steak; and Bites, an innovative small-plates restaurant at the Ritz-Carlton Naples (see Hotels).