Maine late May or Sept
 

Hello. I'm planning a 7 day vacation in Maine. We plan to fly into Boston and spend a 1-2 days in the Boston area at the end of our trip. May looks more affordable and I'm eager to go sooner than later. Sept seems to be better for weather and everything to be opened. I have a long list of towns to visit and I'm trying to figure out best ones to stay in. My kids will be 14, 11 and almost 3 in May. I was thinking of first staying 2 nights in the York, Wells, Ogunquit area. Ending our stay in Acadia National Park. Some of the other towns I have listed are Kennebunkport, Old Orchard Beach, Boothbay Harbor, Rockport, Camden, Bar Harbor. We mostly want to look at the scenery, eat at lobster shacks, light houses, and maybe some kind of boat ride. If it's nice we will check out a beach. Any tips on what towns to stay in? Should we do 2 nights in 3 different areas? Or maybe two different areas and drive to the remaining towns we want to visit?

Here are some ideas:

Stonington, Maine. An authentic fishing village barely touched by tourism. Eat fresh broiled lobster, fried haddock and clam chowder. Take a boat ride along the Down East coast. There are very few authentic fishing villages remaining in America, but this is one of them.

Castine, Maine. This picturesque Down East fishing village features Wilson Museum, a scientific and historical museum campus. A footpath will take you to the historic Dyce Head Lighthouse. Downtown Castine’s Main Street is lined with federal style and Victorian houses. Kayak or take a boat cruise of glittering Penobscot Bay. May be too touristy for some visitors during the high season.

Belfast, ME is a hippy town with a natural foods co-op and community radio station. Walk or bike on the Passy Rail Trail. It was listed by Frommer’s Budget Travel as one of the “10 Coolest Small Towns” in the September 2008 issue. Lots of art galleries.

What great info from PrairieHikerl!
You can’t go in Summer?
If it must be May or September, I would choose September and try to go early in the month. If you choose May, go as late in the month as you can.

We can go in the summer. I was trying to make it more affordable and not as busy by going in the off season.

I would go later in May rather than earlier but keep in mind that it will not be beach weather. You can take coastal walks for sure, but no swimming.

I have included a link for a road trip from Boston to Acadia National Park.
​​​​​​https://lazytrips.com/trip/road-trip...and-bar-harbor

If you stay in or near Boothbay Harbor, be sure to visit the Maine Coastal Gardens. There is a special Giant Troll exhibit that my young grandchildren love!
https://www.mainegardens.org/events-...lls/visit-faq/

Do you have 7 nights for Maine? And then 2 or 3 nights extra for Boston?

The drive from Boston to Acadia is 4.5 hours without any stops. I think Boothbar Harbor would make a good half-way point to stop and spend 2 or 3 nights.

Look at places on vrbo and Airbnb. Costs are not as high as hotels, plus you could make some meals.
Find some places you like and compare costs. With Air BnB or Vrbo, the difference might not be quite as much.

I think May may be too early. Casco Bay Mailboat is always running but other boat trips are probably weekends only IF they habe started for the season. A final activity could be Portsmouth Harbor or Inland River cruise on way back to Boston. Portsmouth to Boston is an easy drive via I95.

there is so much to see and do that I would suggest finding best air b&b type accomodations and then build your itinerary around that location. Double check lobster shacks since some will be weekends only before Memorial Day and after labor day since help goes back to school. We have frequently vacationed 4th of July week because Bath Heritage Days and parade are so much fun. Southern Maine will be very busy in summer as will places like Boothbay but you should have trouble parking at Maine Coastal Gardens whereas you would in downtown Boothbay. I have yet to find lodging in the Harpswell area but it's great for lobster and scenic drives plus conservation areas for short hikes. It's a peninsula area between Bath and Brunswick.

Generally we make our own breakfast, eat a great lunch someplace and go light on dinner. We carry basic picnic supplies so it's possible to buy fresh strawberries and local yogurt at a farmers market to enjoy. A favorite picnic spot is top of Mt Battie in Camden to watch boats in the harbor and coming along the coast. Consider bringing bag chairs with you.

Sept 2021 we rented an air b&b that was a small house in Wells for a long weekend. We liked it better than air b&b condos in the same area but you might want something with a pool.

May = bugs and mud and cold water, and bugs.
September = bugs gone, trails dry, and water less cold...

Did I mention bugs in May?