Aerial view of the Naples coastline with the Gulf on one side and bay on the other

Planning a Trip to Naples, Florida

Naples has a season, a shoulder, and a summer, and they are almost different cities. Get the timing right and everything else about the trip gets easier.

Plan the water first

Season runs January to April, and the calm mornings book out before the restaurants do. Reserve a Naples boat day early and build the rest of the itinerary around it.

Linen shirt, straw hat, sunglasses and boat shoes laid out on teak boat decking in warm light

Seasons & Planning

What to Wear on a Naples Boat Trip (and What to Leave in the Car)

Soft soles, real sunscreen, a layer for the ride home — and the one item that ends up overboard every single week.

5 min read

Child collecting shells in shallow calm water on a Naples beach

Seasons & Planning

Naples With Kids

Naples has a reputation as a retirement town. It is also unusually easy with small children.

5 min read

Aerial view of the Naples coastline with beach, bay and downtown visible

Seasons & Planning

Three Days in Naples: A Plan That Works

Two things a day, a long lunch, and the late afternoon left open. That is the whole method.

6 min read

Calm Gulf water and empty white sand beach in Naples on a clear spring morning

Seasons & Planning

The Best Time to Visit Naples, Florida

Naples has three distinct personalities across the year, and the price difference between them is enormous.

6 min read

27 guides to Naples in total — browse everything.