Much depends on your level of experience and your stamina. If you have done long offshore
passages, just go for it. If you are new to the boat, i.e. just bought it, I would say do the coastal route
. Your time of year and time frame seem reasonable, and much will depend on if the boat has radar
or not. You can leave an anchorage early in the morning with almost o/o visibility with radar
but with only GPS
you know where you are but you dont know where anyone else is. The other advantage of the coastal route is if the crew or significant other burns out you can give them the Amtrack up wind
method. It is much easier to get your mate to love sailing downwind than it is up wind
. Only my opinion!____Grant.