Florida’s beautiful southwest coast is always ready to welcome visitors looking to avoid the winter chill (not to mention the crowds in Orlando and Miami). Naples and neighboring Marco Island provide a perfect blend of city attractions and natural retreats. Here’s our insider’s guide to the best things to do, see and eat.

Editor's note: Please check the latest travel restrictions before planning any trip and always follow government advice.

Christmas lights decorate a palm tree outside a luxury hotel in Naples, Florida in Winter
Why ski when you can go to the Florida Keys © Vladone / Lonely Planet

Take a trip downtown

While much of Naples has a sprawling, suburban feel, its historic downtown is a whole different animal. This beautiful, European-flavored and highly walkable district is jam-packed with high-end luxury shops (Naples is one of the wealthiest cities in America) and a thriving bar and restaurant scene.

Fifth Avenue South is where most of the action takes place, although Third Street South is another lively sector buzzing with nightlife on the weekends. After drinks and dinner on Third, stroll a couple blocks over to the Naples Pier and listen to the waves crash along the shore.

Oceanside eats

In Naples and Marco Island, sometimes the patio views are as much of a draw as the food. But that doesn’t mean you can’t also enjoy a delicious meal at waterside institutions like Snook Inn. The grouper sandwich is the call here and all meals come with free salad bar, where the pickles are must-have, and live music seven nights a week will put you in the mood to party.

Local favorite Dolphin Tiki Bar has a laid-back vibe and a refreshed look after a Hurricane Irma-driven renovation. Meanwhile, CJs on the Bay is another can’t-miss spot for lobster fries and margaritas on a friendly outdoor gazebo.

A bright pink flamingo's head stands out on a brilliant green background
From gardens to wildlife, the natural beauty of southwestern Florida is a warm winter wonderland © Vicki Jauron, Babylon and Beyond Photography / Getty Images

Find a garden paradise

When visiting a seaside paradise like Naples, it can be hard to pull yourself away from the ocean. But Naples Botanical Gardens makes the journey inland more than worth your while, with 170 acres of beautifully manicured gardens perfect for a romantic stroll with your significant other, or some alone time to reflect.

Time your visit to take in special events like live music (with bands setting up on a small boardwalk over a lagoon), art exhibitions or yoga classes. Or if you just want to spread out a blanket and relax in the sun, no one’s going to blame you. (Click here, for the latest COVID-19 safety protocols The Garden has put in place).  

Get out on the water

Dolphin tours, shelling excursions, sunset tours and fishing charters are all popular with visitors, as are private boat rentals. You can select your own watercraft from places like Rose Marina in Marco Island or Dreamlander Tours in nearby Goodland (where delightfully divey bar/restaurant/live music venue Stan’s Idle Hour is the stuff of local legend). There’s also parasailing, wakeboarding, waterskiing and tubing. Surfers take note: wake surfing, a wakeboarding/surfing hybrid popular here, is about the most fun you can have on the water.

Looking down from above on a small motorboat exploring several rocky islands in southwest Florida
Marco Island and the other offshore shelters offer plenty of exciting explorations in southwest Florida © Pola Damonte / Getty Images

Go island-hopping

Marco Island is the region’s most well-known island, but there are hundreds of small islands in the area to explore. Take a local water taxi like Hemingway Water Shuttle to Keewaydin Island, a lesser-known spot off the coast of Marco where you can choose your own adventure via two diametrically opposed experiences.

The river side of the island (where all the boats dock) is a spring-break styled party strip of sand with boats selling booze and booming dance parties, while the ocean side just a short walk away offers the chance for long walks on the beach in complete solitude. Give both a try.

Trippy dome homes

Sure, you could go on a home tour. But for a real taste of local flavor, take a boat ride to the otherworldly Cape Romano Dome House located off the coast of a picturesque island south of Marco. This eerily domed, Star Wars-style igloo structure may have been abandoned as a vacation home in 1992, but it’s still a great place for snorkeling, walking along the nearby beach, and snapping extremely Instagram-worthy photos – although two of the original six domes collapsed during Hurricane Irma.

The pier of Naples, Florida is seen at sunset on a calm sea
Fiery sunsets over the Florida waterscapes are just the right antidote to colder temperatures in winter © Vladone / Getty Images

Cocktails, sunsets, repeat

The west coast of Florida is famous for some of the most eye-popping sunsets in the country, and the Naples area offers plenty of placid locales to take in the spectacular end-of-day color the way it was meant to be experienced: with drink in hand. And while there are plenty of great local bars in the area, for fiery sunsets on the beach your best bets are the hotel bars. 

Sunset Beach Bar at the Naples Beach Hotel & Golf Club is hard to beat, with a happening cocktail scene around sunset and some of the best blackened grouper in all of the land. Quinn’s on the Beach at the Marriott is another spectacular sunset oasis for mojitos and amazing fish tacos, while Sand Bar at the Ritz-Carlton Naples has got the whole tiki bar thing down to a science.

Golf capital of the world

Calling itself “The Golf Capital of the World”, the Naples area is brimming with approximately 90 golf courses, around one-third of which are open to the public.

While it is most well-known for some of the most exclusive private clubs in the world, quality rounds can be played at public courses like the Greg Norman-designed Tiburon Golf Club and Lely Resort, where the course’s Sam Snead’s Tavern is the perfect place to unwind on the patio after a long (but relaxing) day on the links.

Downtown Naples Florida features sail-up boat docks and a quaint historic downtown
The small towns around Naples, Florida are as cool as the main event © Sean Pavone / Getty Images

Small-town charm

Most visitors to the area see the sign along the main road from Naples to Marco Island, but few actually make the turn off onto the side road to the small hamlet of Isles of Capri just north of Marco. Yet this slight diversion yields extremely high rewards with a cozy collection of playful waterside bars and restaurants including the Island Gypsy Café and Capri Fish House. Island Gypsy is the place to take in live music around the fire pits and before you grab dinner next door at Capri Fish House, bring your drink onto their small beach patio and toast to your good fortune.

You might also like: 

Best US destinations for winter sun
First-time Florida Keys: island hopping along the Overseas Highway
Eco-friendly adventures in the Florida Keys 

This article was originally published in December 2017 and updated November 2020.

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This article was first published Dec 7, 2017 and updated Nov 13, 2020.

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