Naples, Florida · A local guide
Written by people who are on this water six days a week. The beaches, the islands, the rainy-day answers and three itineraries you can copy verbatim — plus the honest note that the best of Naples has no road to it.
On the water
Naples is a boating town first. Every item here is unreachable by car, which is exactly why they stay uncrowded on a Tuesday in March.
The one thing on this list you cannot do from shore. A surf boat shapes a rope-free wave you can ride for as long as your legs last, and the same boat covers wakeboarding, foiling and tubing in the same afternoon.
Eight miles of barrier island with no road to it, no concessions and no crowds on a weekday. Anchor in the shallows off the bay side, wade ashore, and you get a Gulf beach that feels private. Bring everything you plan to eat and drink.
South of Marco the coast dissolves into hundreds of mangrove keys. The outer bars hold fighting conchs, olives and the occasional junonia on a low tide, and the runs between islands are usually dead flat.
Naples sunsets are famous from the pier, but the pier is crowded and faces the wrong way for the last ten minutes. Idling just outside Gordon Pass with the engine off is the version people remember.
Resident bottlenose dolphins work the passes and the bay year-round and routinely surf boat wakes. Rookery Bay Reserve protects 110,000 acres just south of the city — slow down, keep your distance, and they come to you.
On land
Six things worth your time between boat days — including the two that save a hot afternoon and the one that saves a rainy one.
The two walkable blocks that anchor Old Naples. Courtyard restaurants, galleries, live music spilling onto the sidewalk, and the best place to eat after a day on the boat when nobody wants to cook.
The classic Naples beach afternoon. Sugar sand, gentle Gulf surf and a pier that has been rebuilt more than once by hurricanes. Lowdermilk has the restrooms, showers and shade that the pier does not.
The best public beach in North Naples, and the park sits right at the pass our Cocohatchee boats run through. Park at the north lot, walk to the pass, and watch the boat traffic go by.
170 acres of cultivated and restored habitat organized by world region. It is the reliable hot-afternoon or rainy-day answer, and the boardwalk through the preserve is genuinely worth the walk.
A two-and-a-quarter-mile boardwalk through the largest old-growth bald cypress forest left in North America, out toward Immokalee. Alligators, wood storks, and in winter the painted buntings. Go at opening.
Tin City is the old clam-shelling and fishing waterfront turned into a tin-roofed row of shops and seafood joints on Naples Bay. The Depot museum across town covers how the railroad made the town in the first place.
Copy these
Actual plans, with actual times, built around the tide and the wind rather than a brochure. Steal them.
Saturday, our busiest day — book early
Glass in the morning, sandbar at noon, Fifth Avenue at night
Monday through Thursday
Same water, none of the boat traffic
Saturday through Monday
The only way to get a Sunday on the water with us
Planning questions
When to come, what it costs, what to do when it rains, and how far everything is.
Getting on the water
For water sports, March through May and October through November are the sweet spot: warm water, calmer afternoons and far less rain than midsummer. December through February brings the best air temperatures and the biggest crowds, with the occasional cold front that kicks up wind. June through September is hot, humid and marked by fast afternoon thunderstorms that usually pass within the hour.
Very. The Gulf beaches are shallow and gentle, the water sits in the low 80s from May through October, and a boat day covers tubing for the little ones and wakeboarding for the teenagers on the same trip. Keewaydin Island and the sandbars near Wiggins Pass are the standard family destinations because you can wade ashore straight off the boat.
Naples rain is usually a fast-moving afternoon cell rather than an all-day event. If it does settle in, the Naples Botanical Garden, the Baker Museum at Artis-Naples, the Naples Depot museum and the shops at Tin City and Waterside all work indoors. On a boat day, the normal move is to duck into the mangrove backwaters and wait the cell out.
Marco Island is about 20 minutes south, Bonita Springs 20 minutes north, Fort Myers roughly 45 minutes, Fort Myers airport about 40 minutes, and Miami around two hours east across Alligator Alley. Southwest Florida International Airport in Fort Myers is the practical airport for a Naples trip.
No, but the water is what separates a good Naples trip from a great one. The barrier islands, sandbars and mangrove backwaters that define this coast have no road access, so a boat is the only way to reach them — and it is the single activity that a mixed-age group will all remember.
