Osoyoos is 400 kilometres east of Vancouver by road (about four and a half hours via the Coquihalla Highway and Highway 3) and 60 kilometres south of Penticton. There is no passenger rail or commercial air service to Osoyoos itself — almost everyone arrives by car.
From Kelowna Airport (the nearest airport with direct flights from major Canadian cities), the drive south takes about two hours through the Okanagan Valley. Penticton Airport, closer but with fewer connections, is the other option.
The Oroville–Osoyoos border crossing connects to Oroville, Washington, about 3 kilometres south of town. If you are coming from Seattle or the American northwest, this is a straightforward crossing. The crossing is open 24 hours.
Within the Okanagan, renting a car is the only practical way to visit the wineries, most of which are not walkable from town.