New England Trip

Would appreciate any feedback on a rough itinerary outline. I have no idea how much time some of these activities would potentially take and if more than one could be done in a day. I’m not married to any of the sequence below.


Arrive Tue Sept 27th
- Stay at Nastucket Beach resort

Wed Sept 28 - Boston
- Freedom Walk
- USS Constitution
- North End Italian meal
- Trillium or Sam Adams
- Other
-
Thur Sept 28th
- Day trip to Salem via Ferry

Friday Sept 29th
- Cape Cod
- Martha’s Vineyard or Nantucket or Block Island
- Go back stay at Nastucket beach hotel or find hotel here or RI?

Saturday Sept 30
- Newport Mansions
- Block Island - maybe?

Sunday Oct 1
- Ogunquit Maine
- Stay overnight or return?

Monday Oct 2
- Possible New Hampshire visit/ driving OR
- Kakumagus Hwy NH OR
- More Time in Maine OR
- Gloucester/Rockport OR
- More Boston

Tuesday Oct 3rd
- Return flight (late afternoon)
 
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We have done the trip a few times, some just Boston and nearby and some on up to Bar Harbor. We enjoyed the Kennedy Presidential Library. We also did a night in Rockport MA and thought that was worth it along with stops in some of the towns along the way such as Marblehead to see the Spirit of 76 painting at the town hall. A visit to Plymouth Rock on the way to Cape Cod is a nice ride with interesting stops like the Cape Cod Baseball League and their museum.
 
I'm jealous. I had a nice trip to New England planned with many reservations in place for Fall of 2020.

I can't add much more other than I hope you have a good time and am anxious to read your trip report if you choose to write one.
 
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That seems to be a very ambitious itinerary to me... probaby a little busier than I would want to be. I would probably include Faneuil Hall Merketplace on Wednesday.... interesting place to stroll through and perhaps have lunch.

Many of the classic Boston area restaurants from when I lived in Boston in the early 80s have closed... Durgin Park, No Name, Anthony's Pier 4, Jimmy's Harborside, Hilltop Steak House, etc. I recently heard that the Kowloon on Rte 1N is still open.

Your wrote Nastucket... did you mean Nantasket? If so, I think you will find Nantucket as a very inconenvient base camp... it is a ways out there... 43 min drive to downtown Boston.

Newport mansions was a good addition.
 
I would not try for Block Island. It is far away from Boston, with a relatively long ferry ride, and you would want to spend some time on the island. In my opinion you certainly could not do that and see Newport and the mansions on the same day.
 
When we stayed in Cambridge in 2019 we took a train to Salem for the day and it was quick and easy.
 
Just to follow up below is a round 2 proposal. It is still probably too jam packed but theoretically doable. Would probably better to do Boston and then either go or go south but not both.

Arrive Tue Sept 27th
- Check in Nantasket Beach Resort (edit: perhaps this isn’t optimal given new plan, maybe something closer to Boston or between Boston and Salem? I had liked the Nantasket suggestion from someone being on the beach by Restaurants and park and ride take train into Boston)

Wed Sept 28 - Boston
- Freedom Walk
- USS Constitution
- North End Italian meal
- Stay night 2 Nantasket (or elsewhere )
-

Thur Sept 29
- To Salem from Nantasket
- Possibly swing by Rockport/ Gloucester if time permit
- Head to stay overnight at Ogunquit

Friday Sept 30th
- visit Ogunquit
- stay 2nd night at Ogunquit

Saturday Oct 1
- Head to Newport RI (3 hrs)
- Stay overnight at Newport
-
Sunday Oct 2
- Mansions at Newport
- Head to/ Stay overnight at Hyannis port

Monday Oct 3
- Cape Cod
- Stay 2nd night Hyannis port

Tuesday Oct 4
- Head to Boston airport after Rush Hr 1.5 hrs
- Flight leaves late afternoon



Edit: a probably more relaxed schedule would be to do Boston and Salem, then either choose
- North up the coast OR
- South Cape Cod area and Newport Mansions

But not both
 
Many of the classic Boston area restaurants from when I lived in Boston in the early 80s have closed... Durgin Park, No Name, Anthony's Pier 4, Jimmy's Harborside, Hilltop Steak House, etc. I recently heard that the Kowloon on Rte 1N is still open.

Sorry to hijack the thread, but are these really all closed? This is a list of my favorite restaurants when I grew up there. Last I heard Hilltop had bought Valle's in Braintree. Is that gone too?

At least it looks like the original Regina Pizzeria is still there. The REAL one, not the "outlet" in Faneuil Hall market (and all the others I now see when I Google it).
 
I enjoyed the Custom House in Boston. It is steeped in Nathaniel Hawthorne lore. Also the waterfront.

In Historic Salem, there are a number of sights to see including the House of the Seven Gables.

Old North Church (one if by land, two if by sea, etc.)
 
Sorry to hijack the thread, but are these really all closed? This is a list of my favorite restaurants when I grew up there. Last I heard Hilltop had bought Valle's in Braintree. Is that gone too?

At least it looks like the original Regina Pizzeria is still there. The REAL one, not the "outlet" in Faneuil Hall market (and all the others I now see when I Google it).


Yes. Hilltop in Braintree has been gone for some time. There is a Toyota Dealership there now. :mad:
 
Yes. Hilltop in Braintree has been gone for some time. There is a Toyota Dealership there now. :mad:
The Hilltop was in Saugus off of Rte 1 South not Braintree.

uv
 
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The Hilltop was in Saugus off of Rte 1 South not Braintree.

But still closed. Now a shopping mall.

Our favorite, Loch Obers is closed as well...sigh.
 
Just to follow up below is a round 2 proposal. It is still probably too jam packed but theoretically doable. Would probably better to do Boston and then either go or go south but not both.

Edit: a probably more relaxed schedule would be to do Boston and Salem, then either choose
- North up the coast OR
- South Cape Cod area and Newport Mansions

But not both

I live in Boston. I would pick the relaxed schedule - probably the south one. I know you must be used to driving distances but a : traffic is horrible in Boston and on the routes in and out and b: I suspect as Bill Bryson said of the UK ( and I found true) the same distance is further here 😀. There will be plenty to do - you won’t be bored and probably will be better friends with less time sitting in traffic jams.
 
Edit: a probably more relaxed schedule would be to do Boston and Salem, then either choose
- North up the coast OR
- South Cape Cod area and Newport Mansions

But not both

Probably a good idea. Have more time to enjoy the places vs rush through them.
Please note that weekend traffic to and from Cape is horrendous. There’s only two bridges and six mile backups are very common.
 
We didn’t drive to the Newport mansions but took a bus tour. They also gave us a few hours of free time in the little town. It took most of the day. When we walked around the historic part of Boston we ran into lots of interesting things to do. For instance the Paul Revere house had people in costumes acting out that time in history.
 
Ah... learn something new every day... I never heard of the one in Braintree but ate at the Saugus location many times over the years.

Now I know why... the Braintree location opened in 1990 and we moved away from Boston in 1986.
 
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...
Saturday Sept 30
- Newport Mansions
- Block Island - maybe?
...

+1 on Newport Mansions

There were a few that offered a guided tour. We just picked one. It was the Marble House owned by the Vanderbilt.

It was good to learn how the rich people lived in the old days. I would not trade my home with its modern comfort for these mansions. Also would not trade my car for how they traveled by boat or by horse carriage to go to/from their summer home.
 
+1 on Newport Mansions
I would not trade my home with its modern comfort for these mansions. Also would not trade my car for how they traveled by boat or by horse carriage to go to/from their summer home.

Mmmmmmm. I have to think about that one! Summers in a Newport mansion, winters in Palm Beach, lots of people to handle the details while you go yachting. A slower pace of life. The Gilded Age before the 16th amendment.
 
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Here are some ideas, I live right by Salem Ma and while lovely, if your not into witch stuff I wouldn’t devote a whole day.

Depending on flight times I might try this.

Arrive on Tuesday and drive to Newport. Eat dinner in town
Wednesday see mansions, tennis hall of fame walk some of the cliff walk. Stay in Newport
Thursday, head to Boston. (~1.5 hours after rush hour). Some of freedom trail, dinner in North End or at legal seafood in the Seaport

Friday, take the high speed ferry to Provincetown at the end of cape cod. (~1.5 hours each way). Used to be town shuttle you could take out to Race point beach, assume still running. Town is interesting, lots of restaurants and art galleries. Head back to Boston on afternoon or evening ferry. As an alternative, if you are big history buffs, skip beach head to Lexington and Concord

Saturday, more Boston

Sunday head north ending up in Ogunquit (depending on weather beach traffic might be issue). It’s about 1.5 drive time, but you could make a day of it hitting a few of these (Salem, Rockport, Gloucester, Newburyport, Portsmouth)

Monday Oqunquit

Tuesday - back to airport

This way you are heading mostly in one direction

Have a wonderful trip
 
We didn’t drive to the Newport mansions but took a bus tour. They also gave us a few hours of free time in the little town. It took most of the day. When we walked around the historic part of Boston we ran into lots of interesting things to do. For instance the Paul Revere house had people in costumes acting out that time in history.

That's why I like to have plenty of 'free time' built into my schedule.

I have only been in Boston once and all I remember is the streets downtown looked like they were built for two guys - one on his horse and the other walking next to the horse.
 
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