My husband and I are flying into Boston (have bought airfare) on a Saturday in June-rent a car and go North on Route 1, up the coastline of Maine. We love Diners Drive Ins and Dive's type places and look forward to some AMAZING LOBSTER ROLLS!! We are thinking of doing a kind of VRBO in one location and make that our anchor, so to speak. We will be there 5 nights, unless we head back to Boston for the last night, hence 4 nights. We are searching for help with:
#1 Where we should rent and stay all 4 or 5 nights (Portland? - KENNEBUNKPORT?)
#2 Names of restaurants that are Amazing food, but not tourist places.
#3 Are there any wineries in that area?
This is basically, a chill get away - 55 years old couple - sight see, eat, drink, a little shopping - possibly a day of fishing
Thanks so much!!!!!

Just a heads --up if your trip is in early June.
My favorite Mount Desert Island lobster pound doesn't open till mid-june:
Fresh Maine Lobsters, Clams, Sea Scallops and Crabmeat - Order Online - Trenton Bridge Lobster Pound

I have no knowledge if this might be typical.

Thanks! I'll check it out. Appreciate it.

Kennebunkport or Ogunquit would both be great places to stay. As you are going before the height of the season you should be Ok with accommodation. I love Ogunquit but not in the middle of the summer. Walking on the Marginal Way is gorgeous. From either location you could drive north or south on the coast and explore. Going up to Bar Harbor is not long enough for 4 days as you would spend most of it driving. The southern Maine coast is gorgeous.

Tough call on where to stay. Last summer we stayed in Scarborough south of Portland in an air b&b next to the Rachel Carson marsh (which is very extensive). We had a Portland activity planned but ended up eating in Scarborough at a local family type place and ruined our appetites the next morning going to Holy Donut so did not go to the Portland restaurant I had earmarked. The current issue of DownEast magazine has revealed some of our favorites. Southern Maine is a day trip for us so we prefer to go to mid-coast Maine when we want to enjoy the best of Maine. Rt 1 is a good route but you are going to have to go off Rt 1 for some of the best eating places. Last year for 4th of July week we stayed in a VRBO cottage out on the peninsula from Damariscotta. It was too far out with no cell or internet connection and meant long drives to most places. But in sweet little downtown Damariscotta Crissy's Breakfast & Coffee is wonderful. I think it appeals to both locals and tourists.

Boothbay was on our explore list because I wanted to go to the gardens. It's fun to wander the farmers market so get a list of Maine's farmers markets. Brunswick is one of my favorites. In June you might be able to get local yogurt and fresh strawberries except it might be a little early for strawberries. Never too early for some local pastries and cheeses. There are wineries in quite a few places including Rockland (nice view) and our favorite because it was our first Cellar Door Winery (but go to the original location in Lincolnville just north of Camden). While hunting down some wineries we ran into Morse's Sauerkraut and Deli. It might be on a bus tour stop but it's in the middle of nowhere, well away from the coast.in Waldoboro.
Morse's Sauerkraut & European Deli

Boothbay won't be too congested in June if it's not a weekend but we stayed in East Boothbay (check out the East Boothbay General Store). Happened on the right day for the farmers market, visited the Coastal Gardens, found a great spot for a picnic (little park on tiny island accessed by footbridge) and went to Karen's Hideaway for lobster rolls etc. https://www.facebook.com/Karens-Hide...5048375954704/ You'll have to find a picnic spot because I can't quite remember where the park was but think it was somewhere near the Coastal Gardens. Good spot to watch kayaks put in. Only one other couple around. Karen's seemed to be locals' choice for lunch based on pickups and guys we saw.

I always rave about McLoon's Lobster shack which will require a drive out past Rockland to So. Thomaston. One of our previous favorites - Waterman's, should you find it on any list, retired. McLoon's is also family operated and a place where you might also see bald eagles. Pretty little working harbor. Nice older teens running the shack but it's now on a lot of "best of Maine" lists so it will be getting crowded if people are willing to get off route 1. Tip: order the lobster roll with a side of hot butter. They put very little mayo on the lobster but what you do is take the pieces which are about to fall off the over stuffed roll and dip them into warm butter. Opens for the season Memorial Day weekend.

In Rockland and actually on Rt 1 is Claws. Take-out kind of place with a covered porch offering a view of the busy harbor kind of industrial looking side of it. Website seems to be under construction but according to facebook they are having a hiring fair this weekend. We went there twice. If you stay someplace in the Rockland area you can go north to Camden and south to Brunswick. You might like Fat Boy's Drive in but we preferred Cameron's Lobster House (I think it's on Rt 1). https://www.tripadvisor.com/ShowUser...ick_Maine.html And the best part about Brunswick is the Harpswell area to the east has several places to explore. On one trip we visited Gurnet Trading Company but it's not on the water.

One of the things about location is the further north, the less tourists (except for places like Bar Harbor) and smaller population results in places that aren't so big. We went to Two Lights on Cape Elizabeth on a rainy day. The place is large and it was mobbed. Due to weather, nobody was sitting outside at picnic tables. I think we ate in our car. McLoon's is a tiny cook shack with a single order window. If you stay north of Portland, you also have a better chance of finding a public lobster supper fundraiser. Mostly you have to watch for signs advertising the supper in front of churches and grange halls. It might not be anything special unless they have homemade pies for dessert and in June there's the likelihood of getting rhubarb pie!

You best go I95 until you get to Maine. You can research Portland in chowhound/northern new England thread. There's plenty just in Portland but you'll have to go further north for a good lobster shack experience.

Any thoughts on where to stay for one night in Kennebunkport? Then going to head North the 2nd day.