You Have: Paddled long distances through mellow water.
You Want: To lead a burly multi-day trip.
The Trip: The North Shore of Lake Superior, in Ontario, is chock-full of mossy forests, Ojibwe Indian ruins, and empty sandy beaches. It’s also plenty rugged. Before tackling it, make sure you can self-rescue (climb back in your boat and bail it out). Then try this 25-mile island-hopping excursion from Gargantua Harbor to Old Woman Bay recommended by David Wells, kayak guide and owner of Wawa, Ontario–based Naturally Superior Adventures. Arrange a shuttle with Twilight Resort (US$120; 705-882-2183) in Montreal River Harbor; they’ll pick you up and drop you at Gargantua Harbor. From there, paddle past Agawa Rock and make for Grindstone Point, an area where erosion has formed smooth rock pools along the shore—perfect for lounging. Along the way, you can pick from beach campsites on several islands. On your last day, hit Still Creek Falls, where a 300-yard hike accesses a series of cascades. Then jump back in your boat and paddle past the soaring 400-foot cliffs of Old Woman Bay, the site of your take-out.
Essential Gear: Superior is rocky and cold, so go with a plastic sea kayak in the 15-to-17-foot range, a Farmer John wetsuit like NRS’s Ultra ($105), and neoprene booties like L.L.Bean’s Vortex ($39). The Canadian coast guard mandates that each boat have a signal device (whistle or flare) and 50 feet of floating rope and a bailer. You can rent everything but the booties from Naturally Superior (from $80 per day).