It definitely can be an adventure!!
I know you will get lot's of great advice here. You'll probably be able to fill a book.
We attended the Annapolis Safety at Sea seminar before my trip, and received a lot of great tips. It has taken place already for 2011.
I'll list a few items that I think are important:
SSB radio and weather fax...or equivalent.
Jennifer Clark does weather routing you might check her website and see if it's worth having her do a plan for you.
I think Herb is still broadcasting...check in with him to get up to date information
Pay attention to your progress while in the stream..you want to avoid going sideways in the wrong direction
Jenifer Clark's Gulfstream
South Bound II VAX498 - Ship routing and weather forecasting
Keep spare clothes in waterproof package
Have plenty of quick and easy energy foods and easy to prepare meals available in case you hit some bad weather..keep dry foods dry! ( watertight)
Have a big thermos so you can make coffee, soup etc and keep them hot for night watches.
Jack lines..( flat webbing), harnesses etc..I'm sure you know this.
Good first aid kit,
strong Lee cloths or lee boards
A way to secure the companion hatch boards from flying out
A way to secure bilge boards from popping out. ( hooks and bungy cords)
Strobes and whistles at minimum attached to life jackets..
Storm sails...Storm jib, and maybe a storm tri....deploy them early if needed
Make sure the bow anchor is very secure.
I don't like glass bottles on board...at sea!
For Fun! Bring a fishing rod..
Stop the boat and take a swim..if the weather is good!
I'm sure I missed a bunch..