Hi,
I'm considering undertaking a trip soon, and I wanted to see what
people's opinions are before I set out. If you'd prefer not to read my
whole post, here it is in a nutshell. I'm 26, in good shape, with
modest sailing ability. I plan to purchase a boat, between 22-27 feet
and sail along the coast of New England for about 1-2 months, hopping
from harbor to harbor. Is this sensible? Now to flesh it out a bit.

I consider myself of "modest" sailing ability. When I was in middle
school I sailed on a river in a day program for youths. It was not the
most intensive thing, but I did pass a test or two, and learn the
basics. Last summer I joined the Community Boating Program (CBI) in
Boston. I've sailed last summer, with a good amount of dedication, but
then this year, I've been going a great deal since April. The boats
I've been on have mostly been 15' centerboard Mercury's. There are
three basic ratings one can get for these boats, and I've gotten the
highest, which I'm pleased with. - Since then I've gone on to the
Rhodes 19, which I really like. I've since been rated for that boat as
well, and can now take other beginners out to teach them. Ratings
involve tacking/jibing, mooring, and man-overboard drills, while under
15-20kt winds.

In addition to that, I've read several books on sailing over the
winter, to which I owe my fast progress on the Charles. I realize the
Charles is NOT the ocean, however, experienced sailers do comment on
how frequent the wind shifts can be there, and how it's good practice.
I have never sailed on real, ocean water.

As for my plan itself, I intend to purchase a boat large enough
to live on, and store food/water, but no bigger than necessary. I put
that cap at 27 foot, assuming it's rigged for single handing. My plan
is to travel at first in very small hops. One harbor to the next
harbor, then moor/anchor for the night. After I build up more
experience I could take longer hops along the coast. I never intend to
be more than a few miles off the coast 1-3, perhaps 5 for carefully
planned spurts.

I've read about coastal navigation. I've also purchased a great
book of charts, which has maps of most every harbor in New England.
Supplementing that, I'd get a basic GPS, and plan out the next day's
trip each evening. I expect to stay each night in a harbor at either a
transient mooring, or anchorage.

So that's the gist of it. I don't want to go too long in this
post, but I've put a good amount of thought into safety systems, first
aid etc. A radio to keep watch on the weather, etc, etc.

Please look this over and get back to me. I don't know how crazy my
idea is. In some ways it seems sedate, but in others, I realize I
could be one simple mis-judgment away from death. Thanks again, your
response is very appreciated.

Thanks,
Dave