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Sailing is a super gear intensive sport, and certainly not cheap! I'm doing my best to find quality equipment and the best prices and I want to share my finds. Click on the products or pictures to purchase.

Foul Weather Gear: I can't say enough good about my foulies!! I've now put them through the serious test of sailing in San Francisco in the middle of winter. I found them through a ton of Google searching on an excellent site called Marisafe. Click on the pictures for the links.
Handheld VHF (Midland Nautico): Also after much Google searching, I found this little beauty. It's super light-weight and surprisingly powerful! HIGHLY recommended over anything West Marine has to offer, and at half the price. The battery pack lasted much longer than I expected and I was able to raise a boat over 5 miles away. THe value pack is a nice treat.
I just bought this LED flashlight (Photon Freedom Fusion) and LOVE it. It's got both white and red LEDs so you can save your night vision. It's also a headlamp and SOS beacon.
Safety Harness Tether: Boy oh boy has this thing come in handy in the rough stuff...a must-have if you're going offshore...but you knew that already ;-) (From West Marine)
Offshore Inflatable PFD Type III: This was a great West Marine purchase; surprisingly comfortable and super durable. Of course get the one with the built-in harness.
Handheld GPS (Garmin 76C): Wow, the screen and interface is fantastic...easy to use when you first get it, then lots of cool features once you get more advanced. A big thumbs up.

Given that sailing stuff is so expensive, I'm a firm believer that sailing gear doesn't always have to come from a sailing store. General outdoor stores are great for warm, comfortable, breathable, and/or waterproof clothing. My favorite online store is Backcountry.com (free shipping!)
These gloves are fantastic!   And of course, long underwear!