January - April
If you want to experience California beach weather at Florida prices, this is the time to go. The humidity is low and, while there can be cold snaps that last a couple of days, normal temperatures start at the 50s in the morning before topping out in the 70s to 80s by mid-afternoon. The monsoons that clobber the area frequently during the summer aren’t an issue, so planning outdoor activities is more certain. Don’t forget to pack sweaters (light and medium), a light jacket and long pants, along with the shorts and T-shirts. Book your flight and hotel accommodations as far in advance as you can to get the best rates and ensure that you don’t get locked out of the dates you want—this is a very popular spot in peak season.
May - September
We said this was “Old Florida,” right? Unlike Miami and Orlando, which hit a different up tempo gear in the summer, Naples gears down with a number of stores, restaurants and museums closed until well after Labor Day. It’s also rainy season—and from June through November, hurricane season. Southwest Florida isn’t especially prone to tropical storms (unlike areas farther north in the Panhandle) but it also isn’t immune. Lightweight, breathable fabrics, swimwear, flip-flops, a beach tote and an extra-large tube of SPF 50 sunscreen will serve you well, as temps are blazing—average highs range from 87 in May to 91 in September—when the sun is shining. With the humidity, it’ll feel like the backside of a skillet. If you forget any of these necessities, don’t worry, there are plenty of places to pick up everything once you arrive, in most cases right inside your hotel.
October - December
October remains sizzling and, in recent years, so has November (those are the last two months of hurricane season), with average temperatures hitting 87 by day and nighttime lows of 68. November sees a drop of a few degrees; then December becomes pleasant, with highs in the mid- to high-70s and evening lows in the mid-50s. The holidays are very festive, particularly downtown, with its decorations and the annual Christmas Walk through Old Naples.