Adventure and Relaxation Await in One of the Happiest Florida Beach Towns

Watch dolphins from a boat, chat with parrots, stay forever.

It came as no surprise when my hometown of Naples, Florida was voted number one in the nation for health and happiness year after year after year after year. The Gulfside city offers everything you could want in a bustling beach community: more than 300 days of annual sunshine, boats next to dolphins, tropical citrusy seafood, palm tree and seashell-filled hotels, castle-like shopping plazas, and turquoise water that rivals many spots in the Caribbean.

A significant percentage of savvy travelers who find themselves in Naples end up going from tourist to local within a year or two, making my little Florida secret feel more and more like the new “it” moving destination. Though you could follow in their sandy footsteps, if you’re hankering for a quick dip down south, you’ll be wanting a crash course on the local knowledge.

So muddle up some mint leaves and mix yourself a mojito. If you’re lucky enough to escape the winter snow and plan a trip to the southwest side of the Sunshine State, you’ll want to check out these coveted places in Naples.

Who's ready for some shopping? | Mint Images/Mint Images RF/Getty Images

Indulge in luxury

Most of us plebeians will be flying directly into Fort Myers’ Southwest Florida International Airport (RSW), though if you’re jetting in private (and a lot of Naples residents do), you’ll be landing in Naples Airport where a chauffeured Bentley will likely be taking you to a Port Royal mansion as you nosh on caviar, count your diamonds, and do everything ridiculously rich people allegedly do.

Jokes aside, Port Royal is the city’s most famous neighborhood, located in Naples’ downtown historic district. Its streets are lined with over-the-top mansions and nestled among twisting mangroves and manicured palm trees. Gawking at these homes, which are worth well into the tens of millions, is an absolute must, especially if you have an interest in real estate (or unrealistic expectations).

Looking to imitate its designer handbag, bedazzled sunglasses, and sparkling jewelry-adorned inhabitants? Be sure to hit up the Waterside Shops—an outdoor mall where you have to cross literal moats to get from Louis Vuitton to Prada.

Audubon's Corkscrew Swamp Sanctuary
So peaceful. I could take a nap here. | Audubon's Corkscrew Swamp Sanctuary

Chat with parrots and walk the boardwalk

Naples’ many beaches are its obvious draw, but there is so much more to the town than surf and sand.

If the weather isn’t cooperating or you’re hoping to escape Florida’s notorious humidity, take refuge at various museums, including the Revs Institute, with over 100 classic and rare cars, and the Naples Holocaust Museum, whose artifacts have been donated or permanently loaned by local survivors and liberators.

If the weather is stunning as usual, but oiling up and getting your tan on just isn’t in the cards, there are plenty of other ways to take full advantage of the sun and the wildlife that thrives in it. Explore the water lily pond and active butterfly garden at the beautifully manicured Naples Botanical Garden, or head to the Audubon Corkscrew Swamp Sanctuary, a 2.25-mile boardwalk among the marsh that is a bird-watcher’s dream.

To get even more up close and personal with animals, be sure to also stop at the Bird Gardens of Naples (around the corner from Corkscrew) to interact with parrots and hear about their conservation. Most of the talkative birds have names and unique personalities, and you can actually feed them almonds through their cages.

I'll order the entire menu. | Del Mar Naples

When you seafood, eat as much as you can

Aforementioned Fifth Avenue offers an abundance of craving-specific fare, though newcomer Del Mar has garnered most of the recent attention. The stunning two-story space with beamed ceilings, industrial light fixtures and plush indoor trees specializes in Mediterranean-style seafood. You’d be remiss to not order the sea bass filet, paired with a sweet heirloom tomato broth, fennel confit, and citrus labneh that is currently—in my humble opinion—the best fish dish in town.

Just around the corner is another seafood institution, USS Nemo, where you can get aioli-basted yellowtail snapper, grilled branzino with sauteed artichokes, and a fried grouper bowl served with crunchy pineapple slaw, candied walnuts, and velvety mango sauce. But the spicy lamb ragu on tagliatelle is my favorite dish in Naples, found at Campiello—a rustic contemporary Italian spot with hand-made pastas and wood-fired pizzas.

You’ll also want to take full advantage of Naples’ famous brunch joints: Skillets for rich, cheesy, egg-topped potatoes and Jane’s Cafe on 3rd for healthier options like smashed avocado toast paired with julienned fresh herbs.

If you’re looking to satisfy a sweeth tooth, be sure to hit up Smallcakes for lemon-curd-filled cupcakes and almond-frosted cookies. Norman Love has also developed a cult following with hand-painted chocolates that resemble precious stones and colorful fruit pastries that are almost too pretty to eat.

And lastly, for those who like a little adventure with their meals, hop aboard the Naples Princess for a sunset dinner cruise, where you’ll not only nosh on delights like clams, oysters, and the chef’s famously crisp and refreshing Caesar salad, but dance the night away as the sky turns amber and the dolphins ride along the ship’s hull.

The Ritz-Carlton Resorts of Naples
Waking up and seeing this? Count me in. | The Ritz-Carlton Resorts of Naples

Sleep in a home suite home

Despite significantly pricey oceanside options, there are plenty of hotels to fit every budget. For the money-conscious, eco-certified and family-friendly Hilton Naples offers an oversized outdoor pool with a convenient beach shuttle, while the Inn at Pelican Bay pays homage to cute but kitschy Florida style with Tommy Bahama-inspired rooms decorated in seashell and palm frond motifs.

If you have the cash to drop, look no further than the Ritz-Carlton, a tropical escape with unobstructed beach views, vibrant gardens, and a world-class spa with over 30(!) treatment rooms. LaPlaya Beach & Golf Resort, just down the street, is another luxurious alternative, having undergone $8 million in renovations to update its balcony-adorned suites with bold flora and fauna decor that celebrates the region’s always-in-bloom landscape.

For a more metropolitan vibe, head downtown to Inn on Fifth, which perches above the city’s most popular shops and restaurants on a strip called Fifth Avenue. It’s also a shell’s throw away from the Pier—a 1,000-foot, Brazilian hardwood pathway into the ocean that is arguably Naples’ most iconic landmark, especially during sunsets.

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Joey Skladany is a contributor for Thrillist.