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Please note these landmarks and their descriptions are accurate as of July 2007, and may change over time.

Adriatic Sea [visit this location]
Adriatic Sea Thumbnail Adriatic Sea Map Thumbnail The launching point for 28 sims of open, sailable water. This is a massive Linden lake located in the heart of the old mainland. Please note that as of this writing, Adriatic is the only sim on the lake itself where you can rez boats. The rezzable area is on the north side of the start line. The start line has a race wind setter. Alternatively, you can launch from Caddo, which has a friendly marina (SZ Designs) with a race wind setter.
Hollywood Thumbnail Hollywood Map Thumbnail Sailing and golf themed private sim community sims with 21 sailable sims connected to Nantucket. This is a beautful area free of ban lines and has a lot of open, rezzable water. The start line has a race wind setter.
Nantucket Thumbnail Nantucket Map Thumbnail New England themed private sim sailing community with approximately 16 sims as of this writing. The covenant for this area prohibits banlines. This area is very beautiful and sports a large, realistic central harbor. The Nantucket sailing community sims are connected to the Hollywood sailing community sims. Much of the water is directly rezzable.
Fishers Island [visit this location]
Fishers Island Thumbnail Fishers Island Map Thumbnail New Sailing community with beautiful scenery.
Sailing Across the Mainland
Long Haul Map Thumbnail This is an incredible challenge and requires a lot of patience. I wouldn't really recommend this unless you're a veteran to SL vehicle travel, and an incredibly patient (or masochistic) one at that. With property lines turned on, you can sail down Linden straits, which are free of ban fences. The danger lies in guessing where the Linden straits continue in the next sim and trying not to run into the periodic ban fences which line the oftentimes thin path. At any one point in time several mainland sims may be experiencing so much lag as to disconnect you if you cross into them. Some points along the path may contain race wind setters. Some straits are so tight and perilous it's almost impossible to traverse them without switching to the inboard motor. If you're in for a challenge, this is one way to do it, but you've been warned!