jdj74

My girlfriend and I are considering a first-time trip to Maine over Memorial Day weekend. We're looking for as quintessential Maine experience as possible in such a short window. We'll likely fly or train into Portland. Looking for good B&Bs or Inns and restaurants. A one-day sailboat cruise and/or a hike would be great. Which town offers all this?

Ackislander

It is pretty early for a sailboat cruise, tho they may be running by that weekend. Be sure to bring jackets, raingear, sweaters, in addition to shorts because the weather in NE much less ME at that time of year is highly unpredictable.

Portland is great: restaurants, bars, a nice museum, and you can take the mailboat to visit the islands for very little money.

Brunswick is a great college town that gives access to picturesque Harpswell and Bailey Island, places that are quintessentially Maine. Between Portland and Brunswick is Freeport, home to LL Bean and about a million high end outlets.

I'm not sure it would be worth going on to Boothbay or Rockland and Camden in the time you have.

isabel

I assume you are going to rent a car. If not, then you'll have to stick to Portland and that will not be a quintessential Maine experience. Portland is a nice little city, and worth a stop, perhaps even staying there but to get the Maine experience you need a car and to drive somewhere. Basing in Portland then a day trip up to Camden would give you a nice taste. There's a hill (they call it a mountain) above the city where you can hike and get great views. A straight drive from Portland to Camden is under two hours but there are lots of detours you can take, and Boothbay is one. So if you have two nights and one full day I'd base in Portland (better restaurants, some shopping, etc) and do a day trip to Camden. If you have three nights and two full days I'd probably still do what I suggested but on the second full day go south for a day trip to Kennebunkport, Ogunquit and that area. There are great lighthouses that you can visit all along these routes. http://www.lighthouse.cc/me.html

dfrostnh

The hill in Camden is Mt Battie. We like to picnic at the top while we enjoy the wonderful view overlooking Camden harbor. Portland is a fun city. We took the mailboat cruise last June and enjoyed it. There isn't a lot of narration but enough. Since it's a working boat, DH enjoyed watching them unload things at each stop.

Both Camden and Boothbay cater to tourists and have upscale shops but I would vote for The Harpswell area suggested by Ackislander. You may prefer to stay in the Brunswick area but travel out to Harpswell for lunch. Dolphin Bay Marina has a popular casual restaurant on the water. If you did make it as far as Rockland, check to see if Waterman's Beach lobster shack is open. There's nothing else around except nice scenery. Enjoy the short hike out to Owls Head light.

If you do decide on Boothbay, the Maine Coastal Gardens has lovely trails.