Re: 1000 Islands
Hmmm... Where to start? I see you're from Toronto, so you will need your Passport, etc. if you want to zig zag across the border (assuming you are actually stopping on the U.S. side somewhere). You can cruise U.S. waters for up to 24 hours as long as you don't anchor or dock anywhere.
As for sights... Kingston is a great city to spend some time in. They have a great marina downtown at the Confederation Basin. Old Fort Henry, great restaurants, access to the Rideau, etc. Plenty to do!
Downriver in Gananoque, you have lots of touristy type things going on. Tour boats, gift shops, summer concerts, etc. A little further down you have Rockport, which has a playhouse theatre, tour boat excursions, etc.
Across from Rockport is Alexandria Bay, NY. Home of Boldt Castle, with requisite tour boats, etc. Lots of nightlife, several resorts, marinas, etc.
Upriver from A-Bay is Fishers Landing, home of Chalk's Marina, Foxy's Restaurant and Bill & Jack's Bait Shop. There's also a winery nearby if you're into those.
A little further upriver is Clayton, NY, home of the world's largest freshwater boats and boating museum, the Antique Boat Museum. Lots of neat little shops, restaurants and galleries downtown, plus a museum of the 1000 Islands. Their town dock has overnight dockage, plus there are a couple of marinas offering the same.
Check out
http://www.1000islands-clayton.com/ for more info on the area, accomodations, activities, etc. Lots of NY State Parks and Ontario Provincial Parks to check out, too, if you're planning on camping anywhere along the way.
As for cruising, pick a direction and go! I've been here my whole life and I make it a practice to get lost several times a summer!
And get a chart!! You'll need it!
- Scott