As Dirty Harry said, " A man's got to know his limitations."
Or rather the limitations of boat and crew, and you will have a spring and summer to learn. Get her on the water and sail often and early, and in progressively more challenging conditions. Include a few over-nights on the hook, to practice anchoring and to understand the rhythm and your needs. Sail a few hours at night, even if you do not intend to - it is a skill you should have.
Clearly you need charts and a simple GPS - you only need a chart plotter if you fell like it.
Limitations include pushing limits only as far as the entire crew agrees, though it is important to have a crew that will sail with focus when the weather turns unexpectedly, rather than complain and second guess.
I took our 27' Stiletto catamaran, only 1300 pounds and not a real cruising boat, around the Delmarva in 9 sailing days (the trip took about 2 weeks each time, including some time spent visiting her grandparents each time) with my 8-year old daughter for crew. We had a great time and repeated the trip 2 more times in following years. However, we holed-up a few bad days and I often chose our route and departure times with respect to the weather.
I expect you may spend a lot of time on the inner passage, and that is OK. Remember, you can stay in when it is too rough outside, but you can't always run for cover when it get's bad. Many of the entrances are a bit tricky in on-shore conditions.
(when asked how he reached the starting holds on a difficult rock climbing problem that clearly favored taller climbers - he was perhaps 5'5")
"Well, I just climb up to them."
by Joe Brown, English rock climber
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