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Romantic mini vacation in Maine or Massachusetts

Pensacola, Florida
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Romantic mini vacation in Maine or Massachusetts

My husband wants to take me to Massachusetts or Maine for our 25 wedding anniversary in August 2015. I want to be able to stay in a nice place and have a lot of walking distances to places to visit in a quaint town. But, I have no idea of where to go. Any suggestions? We will be flying in from Florida.

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Massachusetts
Massachusetts
United States
Maine
Maine
United States
Florida
Florida
United States
Boston, MA
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for Cape Cod, Massachusetts, Martha's Vineyard
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1. Re: Romantic mini vacation in Maine or Massachusetts

Congratulations on your upcoming anniversary. Towns in Mass that come to mind are Stockbridge and Lenox, both in the Berkshires which are wonderful to visit in the summer (that is "season"). Here is a good link to get a sense of what is available.

www.berkshires.org

There are lots of really special B&Bs and inns perfect for this kind of trip.

Other places to consider are Edgartown on Martha's Vineyard, or Nantucket town on Nantucket Island - both of these are are charming, upscale, walkable towns. One thing to keep in mind for these as potential destinations is that August is the most crowded time and expensive time to visit.

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Stockbridge
Stockbridge
Berkshires, MA
Lenox
Lenox
Berkshires, MA
Berkshires
Berkshires
Massachusetts
Edgartown
Edgartown
Martha's Vineyard, MA
Martha's Vineyard
Martha's Vineyard
Massachusetts
Nantucket
Nantucket
Massachusetts
Boston, MA
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2. Re: Romantic mini vacation in Maine or Massachusetts

If you are interested in Maine, I personally love both Boothbay Harbor & Bar Harbor. Portland is also quite lovely with lots of great restaurants & shops.

I love Ann's Point Inn in Bar Harbor (technically Bass Harbor). When in Boothbay we typically stay with friends on Squirrel Island, but I know there are many cute B&Bs in the harbor.

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Maine
Maine
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Boothbay Harbor
Boothbay Harbor
Mid Coast Maine, ME
Portland Harbor Hotel
Portland Harbor Hotel
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Portland, ME
Ann's Point Inn
Ann's Point Inn
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Mount Desert Island, ME
Bar Harbor
Bar Harbor
Mount Desert Island, ME
MA
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for New England
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3. Re: Romantic mini vacation in Maine or Massachusetts

I second the suggestion of Portland, Maine. Stay in one of the hotels or B&Bs/inns in the Old Port. The Old Port is very quaint, with a number of shops and a wide variety of great restaurants, cafes and bakeries. Also, a nice art museum. You can take a ferry out to the harbor.

Another suggestion is Portsmouth, NH. Also a quaint port town, with cobblestone streets, shops and lots of restaurants in the downtown area. Portsmouth has a wonderful outdoor historical museum called Strawbery Banke with a number of restored early American homes with costumed guides.

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Old Port
Old Port
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Portland, ME
Portsmouth
Portsmouth
New Hampshire
Boston...
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4. Re: Romantic mini vacation in Maine or Massachusetts

Another vote for Portsmouth, NH. There is so much to do and see. There are terrific restaurants and summer concerts at Prescott Park, which is beautiful even without music.

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Portsmouth
Portsmouth
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Prescott Park
Prescott Park
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Portsmouth, NH
Cambridge...
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5. Re: Romantic mini vacation in Maine or Massachusetts

Portland, ME, Portsmouth, NH and the Berkshires are all excellent suggestions. If you don't have a car, the first two might be better as they offer a lot in walkable distances.

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Portsmouth
New Hampshire
Berkshires
Berkshires
Massachusetts
Lincoln, NH
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6. Re: Romantic mini vacation in Maine or Massachusetts

Just to add to the fun and confusion, I would consider both Chatham on Cape Cod and Camden, Maine. Both have "quaint" covered, and are very nice towns for walking around. Kendrick's suggestion of Martha's Vineyard and Nantucket are both great as well.

If I had to pick one, I'd lean toward Camden. I'm not much of a beach-goer. If you are, though, I'd think about any of the other spots.

LMM

Oh, and nothing against Portsmouth and Portland -- both GREAT small towns!

Edited: 20 February 2014, 16:58
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Chatham
Chatham
Cape Cod, MA
Cape Cod
Cape Cod
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Camden
Camden
Mid Coast Maine, ME
Martha's Vineyard
Martha's Vineyard
Massachusetts
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Nantucket
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Portsmouth
Portsmouth
New Hampshire
Pensacola, Florida
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7. Re: Romantic mini vacation in Maine or Massachusetts

Wow - such great suggestions! Now I need to work on my vacation with the family and this one! I think I will be busy for a while, but this is the fun type of busy! Ha! Thanks again.

Miami Beach, Florida
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8. Re: Romantic mini vacation in Maine or Massachusetts

From one Mimi to Another:

My favorites would be either Nantucket or Boothbay Harbor and it would be a hard choice to make. Congratulations on your upcoming anniversary and have a lovely trip..

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Nantucket
Massachusetts
Boothbay Harbor
Boothbay Harbor
Mid Coast Maine, ME
9. Re: Romantic mini vacation in Maine or Massachusetts

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