When is the best time of year for riding on Naxos?
On the road to Potamia, December 17, 2015, about 14°C according to my GPS.
Short answer: Avoid coming to Naxos in July and August if you have a choice. Riding is best in spring and autumn.
July/August is the tourist main season, everybody is here. Which means a lot of cars, buses, scooters, 4-wheel-bikes on the road. Which also means accommodation is going to be more expensive. And it's hot. You can ride in the heat, but it's less pleasant and you better take it easy, take precautions, and do a bit of acclimatization. Why bother? Come in spring or autumn. Even our "winter" is pretty much rideable.
But let's look at it in detail!
The climate
Let's talk about the weather then. Wikipedia says: "Climate is Mediterranean, with relatively mild winters and very warm summers." Wikipedia also has a nice climate chart for Naxos. According to the chart, at the peak of the rainy season, it rains on average 8.6 days in December and 8.4 days in January. That is not very good for agriculture (they are ever hoping for enough rain), but for cycling it is pretty decent. My own anecdotal evidence says that in many of those rainy "days", the rain is coming down over night, so I can get a ride in on some of those days too.
The peak of winter
A few years ago I was playing the hard man and going out in rain too sometimes. The last winter I didn't bother any more, on the rare occasion when I can't get in a ride for a couple of days, I call it recovery. My records say that I did 2 (two) rides on the trainer all winter.
Now if you would be here for only a week and chanced on a few rainy days, I guess you could be tempted to don some rain gear and go out anyway. When I still did that, I found it nice enough, as it isn't so cold anyway, with a mean temperature of 13.7°C (56.7°F) in December and 12°C (53.6°F) in January (numbers according to the chart).
Below Moni, December 19, 2015, about 11°C according to my GPS.
The good months
The best months to come to Naxos are really a function of how warm you like it, and how much you fear any chance of rain.
- June, September:
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Perfect if you prefer it warmer.
Warmer, summer temperatures, some hot days, with pretty much no chance of rain. There are already / still some tourists left on the island, so a bit more traffic.
- March, April, May, October, November:
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Perfect if you don't like it so warm.
Not as warm, but still very mild (and the closer to summer you go, the more chance of warm days thrown in). Best temperatures to ride, according to my taste! There are some rainy days here and there. Not much traffic.
- December, January, February:
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Only perfect if it's just not rideable in your place, but you want to get that riding in.
This is what's called "winter" here (Scandinavians, Canadians, and other folks with real winters are allowed to laugh). The last 2 winters we had 3 and 2 snow days each (per year, not per month). Sometimes it rains for 3 or 4 days in a row. I ride all through winter, but it's a matter of taste, flexibility, and preparation. Not much traffic.
- July, August:
- If you really have to, yes, you can ride in those months too. Take precautions for the higher temperatures. Lots of traffic.
Church at Agios Trifonas pass, September 8, 2016, my GPS is showing 37°C around noon - I need some rest in what little shade there is!
Food and accomodation
The availability of accommodation and food (how many hotels and restaurants are open) is directly related to the coming and going of the main tourist season. So in January there are much less choices. Naxos has a life besides tourism too, so you can find a place to stay and something to eat all year round, promise!
In winter things concentrate more around Hora, the port and main town of the island. If you are based somewhere else "out of season", you might want to get a rental car to facilitate transport (car rental is also much cheaper "out of season").
Transport
During the tourism off-season the flight and ferry boat schedules are less dense than in summer. At least ferry boats run every day all year round. If you come to the island by ferry boat, you might also want to plan ahead for the occasion that the ferry boat cannot run due to too much wind. It doesn't happen very often, but it happens. Especially for leaving the island, check the weather forecast some days ahead, and inquire at the local travel offices (e.g. Zas travel). If in doubt and you have to catch a connecting flight in Athens, leave a day earlier and stop over longer in Athens (you can use the day to ride to Cape Sounion).
Beach near Agios Prokopios, May 28, 2016, ca. 25°C according to my GPS.
Note about temperatures shown
The temperature sensor in GPS devices is usually not very accurate. The device is exposed too much to the sun, so they put in some delays and "optimizations". They also differ from device to device, mine shows always a few degrees more than what a friend of mine gets. So use with caution and don't compare to "official" measurements!