Originally Posted by woolswtr
Thank you all very much for all the advice... I really appreciate it. It's good to hear a range of opinions and a lot of you bring up good points. I especially respect CruisingDad comments about putting USCG in possible harms way when someone does something obviously stupid and gets in trouble.
I will mull it all over... and be getting my boat ready. Regardless of Bermuda, I've got a lot of sailing to do this summer!
If I do head to Bermuda, I'll post on here how it ends up going.
Fair winds. Please do consider sailing on crewed, well-found boats first around 200 miles out, in preferably harsh weather. It's 100% of the experience at 10% of the risk of doing it alone in a boat possibly not up to the task.
In the meantime, the U.S. East Coast isn't often a lee shore, so get out there and shake some stuff loose. You have from Boston to Nova Scotia some beautiful and technically challenging (tides, lobster pots, nav hazards, fog) sailing that is also well-served with "outs" should you get in over your head...so to speak!