We base our
boat out of Bucks Harbor in South Brooksville and IMHO it would be a great place for you to start your
cruise. It lies on the east side of Penobscot Bay, which is where you should focus on. You could spend a lifetime sailing between western Pen Bay and Mount Desert Island and never visit all the great
anchorages or see all there is to see. Most of the Maine coast south/west of Pen Bay is made up of peninsulas so you are either
offshore sailing along the tips of the peninsulas or sailing up and down between 2 peninsulas. Casco Bay near
Portland is an exception to that but Penobscot Bay to Mount Desert Island is easily the better and more interesting cruising grounds. If you take a look at a chart of the area, you'll note that there are literally more islands than you can count, some populated by
fishing villages and some oriented more towards "summer people" and some unpopulated and available for you to visit and explore on your own. You'll be charting your own course between islands and will see a wide variety of other vessels daily, from modern superyachts to lobster boats to 100 year old schooners to traditional wooden sailing vessels to the more commonplace
fiberglass cruising sailboats. One really nice thing about sailing here is that it's almost always your choice whether you want to get out in the
wind or "hide" behind the lee of the many islands. So depending on you and your crews preference and the strength of the
wind that day, you can either have a mellow, slow
cruise, or a windy romp out in the open.
There aren't any large
charter fleets in the area but I can without reservation recommend Bucks Harbor
Marine as a place to charter from but I wouldn't delay long because that's a popular time of year and the number of boats he has available is limited. The business changed
ownership last year and the new owner is absolutely top notch in the way he's running the business and is making many improvements as well. I can't imagine anyone better to deal with. Call John at Bucks Harbor
Marine and see what he has available during your preferred time frame.
From Bucks, it's just a few hours sail to Camden, which is a busy tourist town with lots of great restaurants and all the usual stuff that tourist towns usually have. But unless you really want to go there I would recommend you skip it. The harbor is very rolly so unless it's perfectly calm at night you won't get much sleep unless you manage to snag an inner harbor float to tie up to. Directly out in front of Bucks is Deer Isle and dozens of smaller islands such as North Haven and Vinalhaven and Isle Au Haut and so many more. Or you can
head east towards Mount Desert Island (MDI)and spend time there, or circle out around Deer Isle and then
head towards MDI. Lots to do and see in the MDI area, from Acadia National Park to Bar Harbor, to touring Hinckley Yachts main yard. That choice will depend on the
weather and what's going on locally during the dates you are here. If your schedule allows, the last week of July is when the wooden boat
regatta is held and if you are around to see that, you'll never forget it. From 75-100 wooden sailboats of all ages and sizes in a series of races in the area. The biggest
race begins/ends out on the east end of Eggemoggin Reach, about 10 miles from Bucks Harbor. But even if you miss the
race, you might enjoy visiting the wooden boat
school there in Brooklin, which is also the home of Woodenboat Magazine.
Weather and sailing conditions: Weather is usually mild with calm winds at night and an onshore breeze of 10-15 knots building in just after noon and going down with the sun. You've probably heard about the
fog and it can be there, although usually it burns off by mid morning. But at some point you'll probably want to fire up the
radar to help with your situation awareness, but it might be clear all week? Tides are about 10' twice a day and there are ledges(!) down there, so you'll need to pay attention to where you are and not rely on how it looks on the surface, especially when it's calm with no breaking waves to give them away. Just because you cut through there or you saw another boat do it yesterday afternoon, it doesn't mean you won't go aground in that same spot this morning. No big deal but you do need to pay attention to the
chartplotter or paper chart more than you might in a place like the BVI's. But in the coves and harbors where you'll want to
anchor, almost without exception the bottom is covered with thick gooey mud. So that, combined with the wind almost always dying at nightfall, makes for very easy sleeping.
I hope this info helps, and if you do arrange a charter out of Bucks or plan to visit this area, PM me and I'd be happy to give you much more detailed info about various anchorages and harbors, depending on exactly when you'll be here and what sort of things you are most interested in seeing. Good luck and welcome to downeast Maine!