Cozumel is thirty miles long and roughly ten wide, and almost everything built on it sits on the western, leeward third. One paved loop takes in the rest. You run south out of San Miguel on the Costera Sur past the hotel zone, Chankanaab and the beach clubs, round the southern tip at the Punta Sur park entrance, then turn north onto a road with the open Caribbean on your right and nothing at all on your left for the best part of twenty kilometres. At the Mezcalitos junction you cut back west across the island on the Transversal, past the San Gervasio turning, and you are back in town. Sixty-odd kilometres. About two hours of actual driving. A whole day if you use it properly.
That east-coast stretch is the reason this category exists. The windward side of Cozumel has no hotels, no shops, no fuel and patchy phone signal. What it has is limestone shelf, blowholes, a series of beach bars with hand-painted signs — Coconuts up on the bluff, Rasta Bar, Mezcalitos at the junction — and surf that comes in with nothing between it and Cuba. It is also, with a couple of pocket exceptions, not safe to swim. The currents and undertow on that shore are the real thing, there are no lifeguards, and the local advice is consistent: wade, do not swim. Read the signs and believe them.
There are two ways to do the loop. A guided jeep tour puts you behind the wheel of your own vehicle in a convoy behind a lead guide, usually with a snorkel stop, lunch at a beach club and either Punta Sur, El Cedral or San Gervasio folded in. Five to six hours, everything arranged, and someone else worrying about fuel and the route. Or you rent a jeep for the day and go alone, which costs less, takes as long as you want, and lands you squarely in Mexico's rental-insurance system.
That second option needs a plain warning before anything else. Mexican law requires third-party liability cover on every vehicle on the road, and the collision waiver bundled with your credit card does not satisfy it. You will be asked to buy liability at the counter whatever your booking says, and the cheap online rate you clicked is not the rate you pay. Budget for it and it is still worth doing. Turn up expecting to argue and you will lose an hour of your holiday at a rental desk on Avenida Melgar.
One more structural fact worth knowing before you plan: north of the Mezcalitos junction the east-coast road stops being maintained. The track that carries on toward Castillo Real and Punta Molas is unpaved, rough, and off-limits under almost every rental contract on the island. If you break something up there, you are uninsured, unreachable and a long way from a tow.
