There are places you visit and places that stay with you. Naples, Florida is firmly in the second category for our family, and I don’t think that will ever change.
When Ollie was four months old, Ben took paternity leave, and we packed up our little family and spent an entire month in Naples. A full month — long enough to stop feeling like tourists and start feeling like people who actually lived there, at least for a little while. We found our coffee shops and our favorite beach spots and the restaurants we returned to again and again. We watched the sun set over the Gulf more evenings than I can count. We fell completely in love with a city that I genuinely believe is one of the most beautiful places.
If you’re planning a trip to Naples, Florida, I want to share everything we loved. Not a list of the most obvious things to do, but a genuine, personal guide from a family who actually spent time there and would go back in a heartbeat.
Why May Is One of the Best Times to Visit Naples
May sits in a genuinely sweet spot for Naples. The snowbird season has wound down, the summer heat and humidity haven’t fully arrived yet, and the city has a wonderfully relaxed, unhurried energy. The Gulf water is warm and calm and that almost impossible shade of clear green that makes Southwest Florida so distinctive. The crowds are manageable, the beaches are beautiful, and the restaurants — which can get very booked during peak season — are a little more accessible.
A word of preparation: May afternoons in Naples can bring brief passing showers. They’re usually short, warm, and followed by the most beautiful fresh air you’ve ever experienced. They’re part of the rhythm of Florida spring, and once you get used to them, they feel more like a feature than an inconvenience. Plan your outdoor activities for mornings and early afternoons, and save your longer dinners and downtown evenings for when the air is cool and golden.
The Beaches
The beaches in Naples are genuinely extraordinary — white sand, clear water, and a Gulf Coast quality of light that photographers and painters have been chasing for generations. Here are the ones worth knowing about.
Delnor-Wiggins Pass State Park is our personal favorite and the one I recommend most enthusiastically. It’s the least developed beach in Naples, which means it’s the most naturally beautiful — wide, unspoiled, and surrounded by the kind of coastal ecosystem that reminds you why Southwest Florida is so special. The water clarity here is extraordinary. Go early, bring a cooler, and plan to stay a while.
Vanderbilt Beach in North Naples is wider and more open, with a wonderful family-friendly energy. It’s well-maintained, easy to access, and has a beautiful stretch of sand that’s perfect for a long morning walk.
Clam Pass Park requires a short tram ride through the mangroves to reach the beach, which keeps the crowds naturally lower and the experience more peaceful. The boardwalk through the mangroves alone is worth the trip — lush, quiet, and full of wildlife. The water on the other side is some of the clearest you’ll find in Naples.
Lowdermilk Park is the most family-oriented beach in Naples — restrooms, a playground, covered pavilions, and a warm and welcoming atmosphere that’s perfect if you’re traveling with young children.
Naples Beach itself is the iconic central strip, and while the historic Naples Pier is currently undergoing reconstruction as of 2026, the beach remains fully open and as beautiful as ever. Sunset from this stretch of beach is one of those experiences that genuinely stops you in your tracks.
Downtown Naples — Where We Spent Most of Our Time
Downtown Naples was where we found ourselves returning again and again during our month there, and for good reason. It’s one of the most genuinely lovely walkable downtowns in Florida — beautiful, considered, and full of wonderful places to eat and explore.
Fifth Avenue South is the heart of downtown Naples — a walkable strip of upscale restaurants, art galleries, boutique shops… Evening on Fifth Avenue is a particular joy — the light is golden, the restaurants are full, and the whole street has an energy that makes you want to slow down and stay.
Third Street South is our personal favorite of the two — a little quieter, a little more residential in feel, with independent shops, excellent restaurants, and a wonderful Saturday morning farmers market that we made a weekly ritual during our time there. Fresh flowers, local produce, good coffee — everything you want from a Saturday morning in a beautiful place. (This is my personal favorite place — a place where I told Ben at a coffee shop, “I could see myself living here!”)
Tin City is the casual, beachy waterfront alternative — historic fish houses on the Gordon River turned into a collection of seafood restaurants, boutique shops, and local finds. It has a relaxed, unhurried atmosphere that feels completely different from Fifth Avenue.
Mercato in North Naples functions as a town center — restaurants, a movie theater, regular live music on the plaza, and a great energy for an evening out.
Things to Do in Naples, Florida in May
Naples Botanical Garden
The Naples Botanical Garden is one of those places that genuinely exceeds expectations — 170 acres of world-class gardens that feel more like a destination than a local attraction. In May, everything is lush and green and vibrantly alive after the spring rains. The tropical plantings are extraordinary, the pathways are beautiful, and there’s a quality of peace and beauty here that makes a few hours feel genuinely restorative.
On May 23rd and 24th, the garden hosts Family Wonder Days — a wonderful event for families with young children that includes games, activities, and scavenger hunts throughout the gardens. If you’re visiting that weekend, it’s absolutely worth planning around.
Naples Botanical Garden: 4820 Bayshore Drive, Naples, FL 34112 — naplesgarden.org
Naples Zoo at Caribbean Gardens
Situated within the historic Caribbean Gardens, the Naples Zoo is a genuinely wonderful family destination — home to exotic animals including giraffes and tigers, with immersive habitat areas, educational keeper talks, and interactive programming that’s engaging for all ages. We took Ollie during our month there, and while she was quite young, we simply loved being together.
Naples Zoo: 1590 Goodlette-Frank Road, Naples, FL 34102 — napleszoo.org
Corkscrew Swamp Sanctuary
Corkscrew Swamp Sanctuary is one of the most extraordinary natural places I have ever visited. An Audubon-managed old-growth cypress forest less than an hour from the beach — the boardwalk winds through ancient cypress trees draped in Spanish moss, past wildlife and wetlands that feel completely untouched by time. If you have any love for nature or simply beautiful, otherworldly landscapes, this is unmissable. The birding in May is exceptional. (I bring my trusted bird guide for every visit to Southwest Florida! 🐦)
Corkscrew Swamp Sanctuary: 375 Sanctuary Road West, Naples, FL 34120 — corkscrew.audubon.org
Get Out on the Water
Naples’ waterways are genuinely extraordinary and getting out on them is one of the highlights of any visit. Pure Florida runs the largest fleet in Naples — daily dolphin watches, shelling trips, eco-tours, sunset cruises, and fishing charters all departing from Tin City. A sunset cruise in May, with the Gulf water calm and golden and the sky doing something completely impossible, is one of the most beautiful experiences Southwest Florida has to offer.
Get Up and Go Kayaking offers clear kayak tours through the back-bay mangroves — a genuinely magical experience that gives you access to parts of Naples’ natural ecosystem you simply can’t see any other way. (Book in advance as these tours fill up.)
The Gordon River Greenway
Eight miles of trail through preserve land minutes from downtown Naples — the Gordon River Greenway is a wonderful option for a morning walk or bike ride that feels completely immersed in nature while being right in the middle of the city. In May the preserve is beautifully green and the wildlife activity along the trail is wonderful. It’s one of those free, simple, genuinely restorative experiences that Naples does so well.
Where to Eat in Naples, Florida
Naples has an extraordinary dining scene with more than 700 restaurants ranging from casual waterfront seafood to genuinely world-class fine dining. Here are the experiences worth knowing about.
For dinner, Fifth Avenue South is where you’ll find the most celebrated options. Third Street South has a wonderful collection of independent restaurants with a neighborhood warmth that’s hard not to love. For a weekend brunch, Taberna at Mercato serves brunch every Saturday and Sunday until 3 PM.
If you want a fun way to discover multiple restaurants at once, Paradise Food Tours turns Fifth Avenue and Third Street South into a two-hour progressive dinner — genuinely one of the most enjoyable ways to get oriented in downtown Naples and find the spots you’ll want to return to.
Where to Stay in Naples, Florida
Naples leans upscale in its accommodation options, though there are genuinely wonderful options across price points. The Naples Beach Club — a Four Seasons Resort — is one of the most anticipated hotel openings in recent Naples history and worth checking availability for a May visit. Naples Grande Beach Resort and LaPlaya Beach & Golf Resort are both well-regarded beachfront options. For a wonderful waterfront boutique experience, The Perry Hotel Naples on Naples Bay is consistently beloved.
For families or anyone wanting more space and a home-away-from-home feeling, vacation rental condos and homes throughout Naples offer excellent value and the kind of space that makes a longer stay genuinely comfortable. During our month there with a four-month-old, having a full kitchen and living space made everything so much more relaxed and manageable, and I’d recommend that approach for any family traveling with a baby or toddler.
A Few Tips for Your May Visit
Go to the beach in the morning. May mornings in Naples are genuinely perfect — warm, clear, and peaceful. Plan your beach time before noon and your downtown exploring for late afternoon and evening.
Spend at least one evening on Fifth Avenue South. The energy of downtown Naples at dinner on a warm May evening is something worth experiencing. Walk slowly, look around, take your time.
Book boat tours in advance. The best tours fill up in May, particularly sunset cruises and dolphin watches from Pure Florida. Book before you arrive.
Make Saturday morning at Third Street South a ritual. The farmers market, the coffee, the beautiful neighborhood energy — it’s one of the loveliest things Naples has to offer and something I hope you get to experience exactly the way we did. (I can’t wait to go back again in the future for spices!)
Naples is one of those places that changes something in you. The quality of the light, the beauty of the water, the way the city manages to feel both elegant and completely relaxed all at once… it’s genuinely unlike anywhere else. We fell in love with it when Ollie was four months old, and we haven’t stopped thinking about Naples since. I hope you love it just as much as we do.
