Naples, Florida – Did Someone Say Italy?

Some may think it’s a geriatric destination that’s more suitable for their grandparents. While senior citizens (and millionaires) abound, Naples has plenty to offer travelers of all ages. No, it may not be the original, the birthplace of the world’s greatest pizza, but this Floridian version holds its own. While its beaches, cuisine, and cultural vibe will sweep you away, the city truly separates itself from the competition by forcing you to relax. Life slows down here. Especially if you arrive from the northeastern United States, Naples serves as the ideal reprieve from the hustle, bustle, and chaos of America’s economic centers.

Fall and winter are primetime. The “snow birds” from up north flock here to escape the nor’easters that threaten to freeze their souls. During this on season, hotel prices increase and happy hour deals disappear, and for good reason – who doesn’t enjoy beaches and warm weather in January? The idyllic white sand beaches and turquoise waters stretch for miles along the city’s Gulf of Mexico shoreline. Sunsets mesmerize and bid you adieu each night. Come for the beaches, but stay for this city’s cultural beauty and sense of calm.

5th Ave. and 3rd St. South

5th Avenue South in Naples may not have the household names of Manhattan’s renowned strip, but that’s refreshing. Rolls Royces, Bentleys, and Italian sports cars cruise past crowds of tourists and locals alike, many of whom can be found enjoying ice cream on a warm evening from one of the multiple confectionaries along the street. Fresh smells of vanilla, cookie dough, pistachio, and other unexpected flavors escape the open doors of these shops, enticing passersby inside or at a minimum, to one of the benches along the block.

Diners eat al fresco and lounge in the day and night. Italian culture permeates the scene, with pizzerias, trattorias, and cafes offering quality cuisine, cocktails, and coffee. A personal favorite is Caffe Milano, which serves Veal Milanese to die for (among other highlights) in a modern rustic environment. A happy hour with half off entrees and $5 house wine helps too!

At the heart of the avenue is the Inn on Fifth. After staying there recently for five nights, my wife and I added it to our short list of go-to hotels. When we told people we were traveling to Naples, most asked if we were staying at the Ritz Carlton, which is a classic “old money” resort with unfettered beach access and any luxurious amenity your heart could desire. The Inn on Fifth may not be beachside, but if you are a Club Level guest, staff will shuttle you to the beach or anywhere in the area via golf cart or Cadillac Escalade. All guests receive complimentary valet service and the benefit of staying in the middle of 5th Ave. South, surrounded by over 30 restaurants and bars.

A few blocks closer to the water and perpendicular to 5th Ave. South is 3rd St. South. This street claims the crown as the birthplace of Naples. Similar to 5th Ave., 3rd St. South is replete with sophisticated shops, casual and fine dining, local art galleries, and other cultural delights. One of my favorite places here is Tommy Bahama, where you can simultaneously buy clothing, home goods, and lunch or dinner at its crowd-pleasing restaurant. Yes, Tommy Bahama serves food and drink, and not only in Naples, but around the world too (we’ve also enjoyed Tommy’s fare in New York City, Maui, and Honolulu). The Kona Coffee Crusted Ribeye never disappoints and the seafood options are always extensive (mahi mahi, ahi tuna, red snapper, etc.). Their drink menu includes local beers and cocktails that are handcrafted to perfection. Don’t miss their take on the Dark & Stormy.

This 3rd St. and 5th Ave. South corridor is where you want to be when visiting Naples. It is the core of Old Naples, which traces its roots to the 1920s and 30s, while the famous pier that extends to the Gulf of Mexico dates back to 1889. At that time it was the only access point to the city until a shell road was constructed between Fort Myers and Naples in 1918. This history only adds to an already vibrant cultural atmosphere with colorful characters and glamorous surroundings.

Leave the Partying to South Beach

Miami can keep the ultimate title, however, to all things glitzy and glamorous. If you enjoy indulging in more rambunctious activities like us, a place like Naples can be the ideal antidote and change-of-pace. Temptations don’t encircle you here like they do on Duval Street or Ocean Drive. Yes, there is nightlife in Naples, with plenty of places offering live music, entertainment, and late night drinks, but the pace is noticeably slower. The environment has a calming effect that encourages rest and relaxation, not all night binges. You can start your day early as a result, leaving plenty of time to explore everything the city has to offer.

If golf is your game, you will find yourself in heaven here. We took lessons at the Naples Beach Hotel & Golf Club, where my wife made sure not to forget her Prada handbag in the cart. While we won’t be giving any PGA tour pros a run for their money anytime soon, the course and driving range were beautiful. Some resorts offer exclusive golf experiences, allowing you to design your entire holiday around the sport. There is a separate Ritz Carlton Golf Resort further inland that features a premier course and country club experience. They offer shuttle service to their beachside neighbor so you can enjoy the best of both worlds – we might be trying it next time!

The shopping is as abundant as the golf. Whether you find yourself on 5th Ave. or 3rd St. South, or the designer stores at the Waterside Shops, Naples has everything for any interest and budget. I know my wife is eyeing the Mercato Outlets for our next visit.

If you are on the hunt for natural beauty that doesn’t involve the beach, explore the Naples Botanical Gardens. We went on a rainy day that was otherwise a wash from a tanning perspective. The rain held off long enough for us to snap a few pictures. The gardens are more enclosed than others we’ve visited (see the Bronx), and it was my first experience with more tropical flora. I’m not a botany expert by any means, but the diversity was extraordinary. Just be careful near the swamps where gators play!

Another area we enjoyed was Tin City. It’s a stone’s throw away from 5th Ave. South and also houses some of the best locally owned stores Naples has to offer. Whether it is local artist Jennifer Norqual conducting a “Cocktails and Canvas” class, a tasting of fruit wine derived from various citruses and berries, or specialty items like soaps or olive oils, you are guaranteed to discover something new and interesting here. One of our favorite places in Tin City was Pinchers. Stone Crab season runs from mid-October through mid-May, so we were punctual at kicking this one off. These crabs are a South Florida delicacy for a reason – their texture, flavor, and tenderness is so pristine they might as well be seafood lollipops. And at Pinchers, the stone crabs are as fresh as they get. Fishing boats literally sail past as you indulge in the bountiful catch they just unloaded. Once you’ve had your fill, make sure to pick up some Monkey Bread for dessert, or hell, breakfast the next morning.

The Good Life

One of my barometers for measuring the quality of a city or region is their local journalism. I read the Naples Daily News each morning of our stay, and must say, I was impressed. I come from a fairly well-read area in the Pacific Northwest, and the Seattle Times unfortunately can barely compete with this local paper. Which is depressing considering Naples has a few hundred thousand people in its metropolitan area, while Seattle has close to 4 million. The Naples Daily News had substantive pieces on each of the days we visited on topics ranging from their famous stone crabs, to retirement community costs of living (naturally), along with expansive local political coverage. What the paper really showcased though was that you can realize the good life here.

With the city’s close proximity to multiple airports (Tampa, Fort Myers, and Naples) and a 100 mile drive to Miami, it is reasonably easy to arrive and depart, both domestically and internationally. The white sand beaches speak for themselves and the surrounding nature is stunning with waterways connecting neighborhoods like the canals of Venice (don’t forget the nearby Everglades). We also experienced the cleanest public beach bathrooms of our lives at the Naples Pier (they were spotless).

What Naples really excels at though is demanding that you rest, relax, and recharge. Soak up the sun, whether on the rooftop at the Inn on Fifth in the center of the action or along the fine white sand bordering the Gulf of Mexico. Eat fresh seafood and quality Italian fare. Play golf at some of the country’s premier courses. Or simply relax and catch up on your reading. Naples locals told us late one night at HobNob along 5th Ave. South that “you always meet the best people at a bar”, but what I really came away thinking was that you always meet some of the best people in Naples.

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