If you’re trying to figure out the best things to do in Naples, Florida, let me save you a lot of time scrolling through generic listicles. Naples is unlike anywhere else in Florida. It’s not Orlando with its theme parks, it’s not Miami with its nightlife chaos, and it’s not even Tampa Bay with its wide-ranging metro energy — though if you’re curious about any of those, I’ve covered things to do in Tampa Bay, things to do in Miami, and things to do in Orlando in full detail.
Naples is its own thing entirely. It’s refined, unhurried, and genuinely beautiful in a way that feels almost too good to be real. People call it “Paradise on the Coast” and after spending real time here, I get it. There’s a reason it consistently ranks as one of the best places to live in America.
Here are 15 things to do in Naples, Florida that will actually make your trip.
Spend a Morning (or an Entire Day) on Fifth Avenue South
If Naples has a heartbeat, it pulses right down Fifth Avenue South. This is the crown jewel of downtown Naples — a beautifully tree-lined street with around 40 dining options and 40 different shops and boutiques, many of them genuinely high-end without being stuffy about it.
What makes Fifth Avenue work so well is the atmosphere. Most restaurants offer outdoor dining, and since Naples doesn’t allow buildings taller than four stories downtown (there’s a city ordinance), the whole street feels open and airy rather than canyon-like. You can spend breakfast at a café, browse boutiques through the afternoon, have a long lunch somewhere with a patio, and come back for dinner and still feel like you haven’t rushed anything.
Thursday evenings bring live music to the street, which adds a completely different energy — locals come out, the lighting is beautiful, and it turns into one of those spontaneous evenings that you remember for a long time.
Catch Cars on Fifth — Naples’ Biggest Annual Event
If your trip overlaps with Cars on Fifth, rearrange your entire itinerary around it. Seriously.
Organized by the Naples chapter of the Ferrari Club of North America, this is the largest single-day annual event in all of Naples. It transforms Fifth Avenue South into a showcase for hundreds of historic and exotic supercars, drawing car enthusiasts from across the entire state of Florida. The event has been running for over 100 years, which tells you everything about how embedded it is in the local culture.
Even if you’re not a car person, the energy is electric. It’s one of those events where the spectacle is the point.
Explore Third Street South
Just a few blocks from Fifth Avenue, Third Street South is the historic birthplace of Naples. This is old Naples — the original spot for glamour and good times — and it still has that unhurried, charming quality that modern developments struggle to replicate.
The streets here are lined with chic shops, beautiful courtyards, and a variety of restaurants with plenty of outdoor dining. It feels distinctly more residential and intimate than Fifth Avenue, which is exactly the point. Wandering Third Street South on a quiet afternoon with no agenda is one of the most enjoyable things you can do in Naples.
Think of it the way you’d think of a neighborhood in London that doesn’t need to announce itself — it just is.
Walk to the Naples Pier
From Third Street South, the Naples Pier is within easy walking distance, which makes it a natural next stop on any downtown stroll.
The pier is historic and iconic, though it’s currently being rebuilt after sustaining storm damage a couple of years ago. Even during reconstruction, the beach access around it is beautiful and the views out over the Gulf of Mexico are the kind that make you stop walking and just stand there for a while.
Sunset from the Naples Pier is one of those experiences that people specifically travel here for — and it earns every bit of the reputation.
Discover Aqualane Shores and Port Royal
South of the pier begins one of the most remarkable stretches of real estate in the entire United States. Aqualane Shores and Port Royal are consistently ranked among the top 10 most expensive neighborhoods in the country, with average home prices exceeding $3,000 per square foot.
Most homes here sit on deep-water canals with direct access to Gordon’s Pass and Naples Bay. The architecture is extraordinary — less flashy than you might expect and more quietly magnificent, the kind of homes that look like they were designed to be lived in rather than photographed. Walking or driving through these neighborhoods is genuinely worthwhile just as a visual experience.
Eligible properties in Port Royal gain access to the Port Royal Club, an exclusive private club with a beach, dining, pool, spa, fitness facilities, and tennis. It’s a world unto itself.
Spend Time at Naples Bay and the City Dock
Naples Bay is where the boating culture of the city comes alive. The Naples City Dock, the Naples Yacht Club and Sailing Club, and several other marinas line the bay, and there are waterfront restaurants scattered throughout where you can eat with a view of the boats coming and going.
Several condominium communities on the bay have their own boating amenities, and the whole area has a relaxed, nautical energy that’s very different from the shopping and dining of Fifth Avenue. If you can get out on the water — whether it’s a charter, a sailing trip, or even a kayak — Naples Bay is stunning from the water looking back toward the shore.
Visit Baker Park
Not everything in Naples needs to be a splurge. Baker Park is a free 15-acre park that’s genuinely well-loved by locals and worth your time.
There’s a large dog park, a multi-use trail, open green space, and access to the Gordon River Greenway. It’s a good spot to decompress, get some exercise, or just watch Naples residents actually living their lives rather than posing for Instagram. Sometimes that’s the most interesting thing you can do in any destination.
8. Shop and Dine at the Village on Venetian Bay
The Village on Venetian Bay is one of those places that makes you feel like you’ve been transported somewhere in Europe — specifically the kind of waterfront shopping village you’d stumble into while exploring the coast of some Italian or French city. The comparison to a European town is genuinely apt here.
There are over 45 luxury shops and several waterfront restaurants and cafés. The setting along Venetian Bay is beautiful, and this is a popular local hangout that doesn’t feel touristy even though it absolutely caters to visitors. Spend a few hours here and you’ll understand why Naples attracts the clientele it does.
Explore the Waterside Shops
Just north of the Village on Venetian Bay, the Waterside Shops is a high-end outdoor mall with over 60 stores and restaurants. It’s beautifully landscaped with water features and mature tropical plantings, which makes it feel more like a garden walk than a typical mall experience.
This is where you’ll find designer brands alongside good restaurants for a mid-shopping lunch. Even if you’re not a heavy shopper, it’s a genuinely pleasant place to wander — the landscaping alone sets it apart from most retail environments.
Head to Lowdermilk Beach and Park
If you want a beach day without the Ritz Carlton prices, Lowdermilk Beach and Park is the answer. This public beach has good parking (relative to Naples, where parking can be tight), solid facilities, and a beach that can comfortably handle a good number of visitors without feeling overcrowded.
It’s a local favorite for families especially — there’s a playground, picnic areas, and easy beach access. It’s the kind of beach that reminds you why people move to Southwest Florida in the first place. I’ve had equally relaxed beach days here as I’ve had on some of the more celebrated Gulf Coast beaches covered in my guide to things to do in Destin.
Vanderbilt Beach and the Ritz Carlton
For the more elevated beach experience, Vanderbilt Beach is one of the most popular in all of Naples. The Ritz Carlton has been anchoring this beach for years, offering five-star beach service that is exactly as indulgent as it sounds. Even if you’re not staying there, the beach itself is public and the vibe around it is great.
There’s a parking garage nearby which helps significantly, and the stretch of beach here is gorgeous — wide, white, and backed by the kind of clear Gulf water that photographs too perfectly to look real.
Pelican Bay — The Active Community by the Gulf
Pelican Bay is one of Naples’ most celebrated communities, and even if you’re not a resident, it’s worth understanding what makes it special. It’s a large gated community stretching about 3 miles along the bay with 27 holes of championship golf, racket sports, and — most remarkably — a mangrove forest that separates the residential area from the shore.
Through that forest run boardwalks that lead to 3 miles of private beach, with two restaurants on the water — one on the north beach, one on the south. It’s one of the most thoughtfully designed communities in Florida, and the natural preservation of the mangroves is something you rarely see in heavily developed coastal areas.
Mercato — Live Music, Food, and Events Daily
Mercato on Vanderbilt Beach Road is a modern shopping and dining complex that brings a more casual, social energy to North Naples. There’s live music daily, regular “Movies on the Lawn” events, Cars and Coffee meetups, and a rotating calendar of activities that keeps the place buzzing throughout the week.
It’s a comfortable contrast to the more formal dining of Fifth Avenue — still good quality but with a livelier, more spontaneous atmosphere. This is where Naples comes to be social without ceremony.
Celebration Park in East Naples
East Naples is going through a real transformation right now, with new developments moving in because of its proximity to downtown. In the middle of all this, Celebration Park stands out as one of the most fun, unpretentious spots in all of Naples.
It’s essentially a food court with an industrial aesthetic — food trucks, a bar overlooking the waterway, communal seating, and a come-as-you-are attitude that feels refreshing in a city as polished as Naples. It’s the kind of place that reminds you that great food and good company don’t require white tablecloths.
Honestly, it reminds me a bit of the kind of laid-back waterfront food scenes you’d find in Puerto Rico — casual, community-driven, and genuinely enjoyable.
Play Golf — Because Naples Is a Golf Town
Let’s not dance around it. Golf is a major part of life in Naples, and if you play, this is legitimately one of the best places in the country to do it.
Between the gated communities along US-41 and the interior, there are dozens of courses, many of them private but several with public or resort access. The Moorings Golf and Country Club is a member-owned club with an 18-hole course nestled in one of Naples’ quieter neighborhoods. Pelican Bay has its 27-hole championship setup. And there are numerous others throughout the area.
Even if you’ve played great courses — and if you’ve explored destinations like Tauranga, New Zealand or the courses around Harrogate, England — the combination of the Southwest Florida climate, the course quality, and the sheer density of options makes Naples a genuinely special golf destination.
