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AllenI've sailed the Mid-Coast Maine area a few times on a variety of boats. Most recently, last year we sailed up from Marblehead to Casco Bay on my C320. I'd be glad to share my route & waypoint data with you (send me an email at: rdoesche@rcn.com).Casco Bay is very nice -- many islands and varied conditions, ship traffic, etc. Casco should be at least a one-week excursion in itself. Portland at the southern end is basically an overnight sail from Boston, and has the full range of marinas & yard services. The city itself is quite nice, too. We used Spring Point Marina for an overnight stop point. At the northern end, we anchored up in Quahog Bay; it's a beautiful spot tucked inside of Sebascodegan Island. We've also stayed at South Freeport (Brewer Marine); the entry channel from the Bay requires careful attention to avoid the shoals, but isn't a big problem.Penobscot Bay & the interconnecting waterways out through Mt Desert Island are fabulous. Many beautiful islands, lots of scenic boating (the Maine Windjammer fleet) plus fairly protected waters. We chartered there years ago doing a Rockland - Camden - Belfast - Castene - Brooklin - Stonington - Rockland loop (would have done more except for Hurricane Floyd interrupting our plans).The area inbetween Casco Bay & Penobscot Bay (e.g., the "outer islands" -- Seguin, Monhegan, etc., the rivers, Robinhood, Boothbay Harbor, etc.) represents much interesting and challenging sailing too. Challenging in terms of currents, shoal bottoms, weather, etc. There are a couple of photos of these areas posted at the C320 International Website.I've never sailed into the lower Maine coastal ports, but have visited many by land. My general impression was that there isn't much to offer between Portsmouth & Portland (I'm sure many with more local knowledge would dispute that observation, though!). The harbors are faily small, and the access to the Gulf of Maine can be constricted. Transient services is limited in some, too.For a two-week window, I'd suggest sailing directly up to the Penobscot Bay area and spending most of the time there. Going north is generally a broad reach with the SE prevailing winds in summer. Watch out when they start clocking to the west -- generally will bring storms. Going south you may do a lot of motoring into dead-on winds and seas, so watch fuel consumption carefully. You'll probably have to hop your way south -- e.g., Portland, Portsmouth, Gloucester -- for refueling & rest points.Getting up to Nova Scotia would most likely exceed your two-week limit. Friends who have sailed there liked the area a lot. Just remember, if sailing into Canadian waters you'll need an FCC station license for any VHF, HF/SSB/SATCOM, and RADAR emitters on-board, plus any applicable operator's permits/licenses to use them. Also, you can't legally land on any Canadian territory without first clearing customs.--Ron