Hello, Bert. Welcome to Cruisers Forum!
I've not done that entire
passage, but most that I'm aware of make two legs of it--Chesapeake to
Bermuda, and then wait for favorable winds before shoving off for the
Azores. June is a good month for the trip, weatherwise. We had some very rough
weather from the Bay to
Bermuda in June, but nonetheless, your chances for fair winds are greatest then.
Consider linking up with Herb Hilgenberg,
Southbound II VAX498, for weather routing
advice. You can listen to Herb on 12359.0 kHz at 2000 GMT daily. Those wanting custom routing services sign in to his net from 1930 to 2000 with their
boat name and location. Herb listens but doesn't acknowledge the sign-ins, but then will hail each
boat in turn to offer
advice and a local weather
forecast during the session. This is a hobby for Herb, and he charges no fee, but I do know that some cruisers will send him a voluntary contribution to help offset his costs.
Here's a link with a lot of info on sailing into Bermuda -
Yachts Sailing to Bermuda . If a gentleman named Bernie greets you at the Customshouse
dock, take his advice. He's a private citizen who's been welcoming sailors for years, if not decades. The St. George's
Dinghy and Sports Club is a great place to stay while in Bermuda.
Again, a warm welcome--hope you enjoy the Forum.