First Time to Maine - Itinerary Help!
 

Planning an early/late summer trip to Maine with our family of 7, most likely either May or September. Our group includes our two adult children and spouses, plus one baby (less than a year old). My husband and I will have a more extended trip than the others, as we plan on making this a two week trip from New Jersey, one couple may stay a week with us, but the other couple and baby will mostly likely only be there for a long weekend. Places to stay would likely include the areas of: Kennebunkport, Rockland, and Bar Harbor, and wondering which area would be better for the few days the one couple and baby will be with us. Our initial thoughts are to spend 2 or 3 nights in each place. Thinking of starting in Bar Harbor and working our way down to Portland, where hubby and I may take the ferry to Nova Scotia; then possibly ending the trip at the south end around Kennebunkport or Ogonquit before heading home. Would love to be where there are activities - maybe kayaking, hiking, golfing, etc. for those who are interested. Would love to visit some charming towns/fishing villages with gift shops, lobster, and restaurants (think Cabot Cove from Murder She Wrote!). It would be great to be near the water/on a beach for one of our stays, although we won't be sunbathing. Obviously, we will want to visit LL Bean! So, with all of that in mind, do you have any suggestions on where to go/where to stay? I was thinking for the few days when the whole family was together, I'd like to either stay at a nice resort or rent a cottage, house, or large suite, as long as a crib could be provided. For the rest of the trip, when it would be only one or two couples, we would consider a nice B&B or a resort or nice hotel. Looking for scenic Maine and hoping to spend time in each of the different areas - southern coast, mid-coast, and downeast. Thank you in advance for any suggestions you can provide!

Choose September

If you're big on shopping, you'll want to include a day in Freeport and/or Kittery. Portland is the largest city in Maine, but not huge by any means -- still has good restaurants, a good art museum, good historic houses. I'd spend 2-3 days in the York/Ogunquit/Kennebunkport area. Camden/Rockland/Wiscasset are also well worth a couple days. Bar Harbor and Acadia National Park definitely merit at least 2 days.

I second September--always my favorite time in Maine.

I love Bar Harbor/Acadia, but stayed here for a couple of nights a few years ago, and it struck me as a perfect place for a large family group:
http://www.glenmoorbythesea.com

Definitely September. You don't want to be in Maine in May during black fly season.

Go right after Labor Day.

It is going to be complicated moving around a group of shifting size. Mom, Dad for a week, mom Dad plus 2 for a week, all four plus 3 more, for a long weekend (4 days?) plus Activities, land-based and sea-based. Sounds like a job for an Excel spread sheet. Houses and resorts will go by the week, and inns and B&B's can't accommodate a group your size.

If you pick Camden-Rockland as the large group base, there is golf to play at the Samoset resort, a very good art museum and a car museum to visit, windjammer cruises, a day trip to Bar Harbor and/or one of the islands, antiques, cute shops, a Cabot Cove in Rockport, etc. Move to Portland for the rest of the trip. Easy access to Freeport and the coastal places like Kennebunk and Ogunquit. Or not. You can be in the White Mountains in an hour for Something Completely Different.

If the family with baby could stretch to more than a long weekend, it gets easier: parents do Bar Harbor etc for four days, family does Mid-Coast (Camden-Rockland-Rockport) for a week from a resort, everyone accompanies Mom and Da to Portland with a stop in Freeport before everyone goes his separate way.

What you can't much do is go to the beach to swim or wade, though it is warmer in September than earlier. Maybe south of Prout's Neck, but there are other issues down there.

We don't usually go to Maine in May but mid-June could be decent. I agree that September is the best choice of the two BUT the really good lobster shacks on the water are usually only open weekends after Labor Day. You'd have to check each website. We have two favorites near Rockland: McLoon's and Waterman's. Both are outdoors but Waterman's has a covered porch. Of course, there are plenty of restaurants that are open year round but we like the picnic tables by the water atmosphere.

Glenmoor by the Sea in Lincolnville just north of Camden is a great suggestion.

Actually, I did do a weekend in Wells last May. You can park by the beach and it's not as crowded as summer. You might look into The Dunes of Ogunquit for lodging. They have a variety of accommodations but not as nice as Glenmoore. About the only thing I really like about southern Maine is the Ogunquit Playhouse and I thought a cooking "class" (it's really a demo) at Stonewall Kitchen was fun.

I think the Rockland area is a great suggestion due to the museums and shopping. There is also a winery. Somehow we kept missing nearby Rockport which has a wonderful park/marina. A great hiking opportunity that would require a day trip would be Monhegan Island. We took a boat out of Boothbay Harbor but there are other locations with boats to Monhegan. We saw short windjammer cruise out of Rockland in June. May might be too early for cruises. Check schedules.

If the couple with baby have a backpack for the baby, there are some easy, short hikes in the Harpswells area east of Brunswick. Of course, if I recall correctly, the Marginal Way in Ogunquit is paved so could handle a stroller. There are condos you can rent in the Wells area. We aren't hikers so we haven't hiked Mt. Battie in Camden but the auto road is great and we like to picnic at the top because the view is great. This might be a good activity with the little one but you would need to bring blanket. We just take bag chairs in the car. Camden also has some nice shops. Cellar Door winery tastings are fun but I like the original location in Lincolnville best.

You might have difficulty with reservations for the third weekend in September in the Lincolnville area because that's about the weekend of the Common Ground Fair in Unity. There's hardly any lodging in Unity so we have had to stay in Lincolnville to go to the fair. It's an amazing event if you are interested in organic gardening and living. Great food and lots of workshops and great children's play area (but no midway).

Keep in mind that southern Maine is a popular weekend getaway place so I would make lodging reservations soon for that area.

If the parents actually want to have some beach time with the baby, Ogunquit would be a good choice. As the tide goes out, shallow pools are left behind in the river there, and as they warm in the sun, become a great place for little ones to play, quite unique in cold-water Maine.

Fabulous suggestions from everyone ...thank you! I will sort through all of your responses and make a plan. The one thing I can say for sure is that we will plan on September ... I have no interest in meeting up with the black flies of early summer! A few people have mentioned Glenmoore by the Sea, so I will look into that, although some posts have said the accommodations were very dated, but what the heck. I am not necessarily holding out for a 5-star resort! Interesting that the great lobster shacks are only open weekends in September ... thank you dfrostnh! Also, Ackislander, thanks for your great suggestions!

Look at Caravan Tours which has a one-way tour ending in Los Angeles, and at least includes an overnight at Yosemite.

Caravan seems to have very good reviews and has been in business for 60 years.