Naples is located far enough south for the city to enjoy a warm and sunny climate even during the winter months. The waves are usually small and manageable, and the water tends to be shallow at a considerable distance from the coast. The main break in Naples is the most consistent and the most surfed of all area jumps.
The north side tends to launch at the dock, while the south side tends to be a longer, but softer wave; however, on large cold fronts, the north side is blown, but the south side has the bowl. The beaches south of Tampa Bay tend to have larger and better waves than those in the north of the bay. To be able to travel with a surfboard, you'll need waves of at least 2 or 3 feet in height. The most consistent waves for surfing occur in the colder months, from December to March, so you'll need a wetsuit.
So, while beaches aren't what make the Keys special, there are still some pretty special beaches in the Keys. Although Florida doesn't have a landscape as diverse as the Golden State, it has miles of incredible beaches and life is very focused on the coast. The best reported conditions for surfing at Naples Pier occur when a south-southwest swell is combined with a direction of the sea wind from the east-northeast. Very warm air temperatures and very hot water (30.4°C) also at the Naples pier, warm enough to wear shorts and an anti-eruption vest in the waves.
