If you're planning to circumnavigate Iceland—or cover any distance on the island, really—you'll first need to decide which way to travel. The internet seems to lean in favor of cycling clockwise, from Reykjavik to Akuryri and continuing on, citing prevailing winds. Thankfully, we ignored this advice during our ride, for a few good reasons.
First, Iceland is a circle. With the exception of cyclones, winds generally don't travel in circles around large areas of land. That means you're going to get headwinds (and tailwinds!) regardless of your direction of travel. I read somewhere that a bike tourist paid an Icelandic meteorologist to look into this issue a few years back, and the meteorologist found that one traveling clockwise would have favorable winds about 55% of the time, while one traveling counter-clockwise would have favorable winds only 45% of the time—so a little advantage for clockwise travelers, maybe, but you're still dealing with lots of bad winds either way.
If you were to head north from Reykjavik to take advantage of those slightly-more-favorable winds, you'd spend your first week or two in Iceland slogging clockwise along the least enjoyable section of the Ring Road at the very start of your trip. The busy (by Icelandic standards, anyway) highway to Akureyri doesn't really offer a whole lot of sights—at least compared to the absolutely beautiful south—and it's a lot of hills and a lot of long stretches and, still, a lot of headwinds to deal with. By contrast, the southern edge of Iceland is really flat, really beautiful, and littered with gorgeous waterfalls and adorable towns and interesting formations every ten or twenty kilometers.
We met a wonderful solo cyclist about halfway into our journey—right as we were venturing into the north and she was entering the south. We were headed counter-clockwise and feeling great; she was headed clockwise and seemed to be having a rougher time of it. The north is simply more challenging, and while one may be inclined to save the best for last—getting the upper half out of the way first before enjoying the leisurely southern stretch—this approach has its risks. For one, things can go wrong: frames can crack and parts can break, and with virtually no bike shops outside Reykjavik, a repair is likely going to involve a timely and expensive trek back to the capital. If time is limited, this can mean an end to one's trip altogether, and it'd be a terrible shame to not have experienced southern Iceland before heading home. Likewise, mental and physical stamina have limits, and the last thing you want on your Icelandic adventure is to enter southern Iceland in bad spirits, with cycling fatigue or overuse injuries bogging you down.
And even if nothing goes wrong, it's just tough to predict how much time you'll want for the falls and fjords of the south and southeast. You're going to want to stop—for pictures, for picnics, for frequent hot cups of tea at the foot of a glacier or long hikes up in the mountains or soothing baths in geothermal pools, and while it's easy to rush through the north without missing much (or catch a bus if you're really short on time), you might find yourself stressed and skipping a whole lot if you're traveling clockwise and have a return flight awaiting you at Keflavik.
Finally, you can get around the whole headwind headache with one simple trick: bike at night. While not always the case—and definitely not possible in colder and darker months—we found that the winds died down dramatically past 9PM, and the sky stayed absurdly bright in July: bright enough to cycle comfortably until midnight or 1AM. Less wind is made all the better by less traffic and seemingly endless sunsets.
Of course, there's no wrong way to cycle. We headed counter-clockwise and had an amazing time; many others have gone clockwise and had just as much fun, maybe more; and some rode through the highlands and largely avoided the decision altogether. Thoughts, questions, or impassioned defenses of the clockwise route? Let us know in the comments below—and whichever way you choose, may the winds be forever in your favor.