Hi there

My fiance' and I will be heading to the USA in June 2018 for three weeks (flying in and out of JFK) for our honeymoon!

Half of our time will be spent in NYC as my fiancé's has never been, but we thought it might be a good idea to spend the other half doing a road trip to (and around) MA.

We have about 10 days for the road trip.

I was thinking:

8 June 2018 - commence road trip from NYC

So far we are thinking to visit (in no particular order)

• Newport (activities include: Cliff Walk, mansior tour)
• Martha's Vineyard (activities include: whale watching)
• Cape Cod
• Nantucket
• Maine
• Mystic
• Salem
• Boston
• Yale or Harvard?
• some sort of shopping outlet (happy to dedict a whole day doing this, as I want to confine shopping to one day)

We are still very early in our planning. Does anyone have any input or suggestions?Also, any recommended routes we should be taking?

Any suggestions on places we 'must' visit. We love architecture, museums and food. We are very much go go go people and like to take in as much as possible while we are on holidays.

Thank you all so very much
Cat

We have driven twice from Boston to Maine. Cape Ann is our favorite area to drive. Rockport reminded us of The 17 Mile Drive along our Monterey Peninsula in CA. We mentioned that to the inn-keeper and she said they were just there (in CA at Monterey) and said it reminded them of Rockport!

We enjoyed an overnight in Concord and visited Orchard House, Walden Pond, and Sleepy Hollow.

The Italian district in Boston is a fun neighborhood with some great Italian restaurants. If we go again, we would drive Cape Ann again.

A week and a half in NYC is a great amount of time to spend. There's a ton of worthy stuff to do, and loads of top quality restaurants to patronize.

If you're looking for serious outlet shopping, a good option is southern Maine, either Kittery (right on the border with New Hampshire) or Freeport (further up). You would have to drive to Kittery, but Freeport can be reached by the Amtrak train.

There are loads of great easy day trips from Boston. Salem, Concord, New Bedford, and Plymouth are arguably the pick of the litter depending on your interests, but Lexington, Gloucester, Rockport, Marblehead, Ipswich, Lowell, and Newburyport are all well worth considering.

Yale vs. Harvard? Both are well worth visiting, sporting excellent quality museums and interesting architecture. Cambridge is a notably more attractive city than New Haven, though pizza in the latter city is justifiably famous (Frank Pepe's, Modern Apizza, and Sally's being the major options). Either will be well worthwhile, and both would be a reasonable choice.

Newport is ground central for huge, gorgeous historic mansions and you could spend several days there touring them if you wanted; the Cliff Walk is also well worth doing. Good food choices also. Mystic is well worth the day also between the Mystic Seaport Museum and Mystic Aquarium.

Boston requires ideally at least three days, one for the Freedom Trail, one for the Gardner Museum and Museum of Fine Arts (the latter is a large place), and one split between the Kennedy Presidential Library and Cambridge (Harvard). But you can find other good attractions as well. Agreed that the North End (bear900's reference to the Italian district) is a good place for Italian eats, but do your homework to separate the excellent places from the tourist traps -- it conveniently lies right along the Freedom Trail. Will happily suggest some good Italian places on request.

With ca. 10 days in eastern Massachusetts, you should have no trouble finding a few days to devote to Cape Cod, Nantucket, and Martha's Vineyard. Choosing a day at a couple Cape Cod towns makes sense: good options would include Provincetown (reachable as a day trip via ferry from Boston in season), Sandwich, and Chatham. If you drive and are here during summer, however, it's a good idea to avoid traveling over the weekend, as traffic can be really tough. One or two days each is about right for either Nantucket or Martha's Vineyard.

Besides Kittery and Freeport, Maine is well worth some time if you can spare it. Portland, southern Maine towns like Ogunquit and Kennebunkport, the Camden/Rockland/Wiscasset region, and Acadia National Park are all fine options.

• Newport (activities include: Cliff Walk, mansior tour) - last fall we did two mansion tours: Beneath the Breakers and Servants Life, both of which were on other aspects of the building and life and less about elaborate furnishings. Beneath the Breakers included structural details that were fascinating as well as info about plumbing and how they brought coal into the mansion without bothering the family.
• Martha's Vineyard (activities include: whale watching) - make sure to see the Camp Meeting gingerbread houses. Ferry goes to different places at different times so choose accordingly as well as do an island tour.
• Cape Cod
• Nantucket
• Maine - you have to go thru NH to get to ME so I recommend Portsmouth NH, Strawbery Banke Historic Area and a boat trip either the harbor or inland rivers. A drive from Strawbery Banke using Rt 1B goes through lovely New Castle and the beautifully restored historic Wentworth Hotel. Private mansions are on coastal 1A. Portland ME is great for restaurants and fun Old Port area. Kittery outlet shopping is on the other side of the bridge from Portsmouth. Since southern ME is fun to explore you might want to base in this area for a couple of nights. But Camden further north is gorgeous and home to windjammers. I don't think you have enough time to include Acadia.
• Mystic - I think you can include the Native American Museum at Foxwoods between Mystic and Newport. You do not have to go to the casino. It's in a separate area. Will take at least a half day.
• Salem
• Boston

A few things to keep in mind. To take your car on the ferry to Nantucket and Martha's Vineyard in high season requires reservations that sell out months in advance. You can leave your car and take the ferry as a passenger but for Martha's Vineyard then you would need a way to get around as it's quite large. Nantucket you can see a lot without a car. Also traffic going onto or back off of Cape Cod is horrible, especially on weekends. You could spend your whole time just on the Cape, Nantucket and the Vineyard but there is so much else to see in New England that I personally would probably skip those places. You can take a whale watch from the mainland, you don't need to go to the Vineyard for that.

Starting from NYC you could drive up through Connecticut and stop at Mystic Seaport, then on to Newport. Then Boston. Most guide books have numerous walking tours you can take in addition to the Freedom Trail. Definitely check out the neighborhoods including the North End. From one hotel in Boston (or you could stay in Cambridge) you can do both Boston and Cambridge (Harvard).

Then stop in Salem on your way to Cape Ann - Rockport and Gloucester.

On your way to Maine you can then stop in Kittery just over the boarder from New Hampshire, for outlet shopping if that's what you want. A stop in Portsmouth NH is also worthwhile.

Then I'd continue up the coast stopping in York, Ogunquit, and Kennebunkport before Portland. There are several lighthouses you can visit along this stretch. Depending on your speed of travel (how long you want to spend in each place) you could continue up as far as Camden and Rockport. I don't think you have time no matter what you do to go all the way to Bar Harbor/Acadia National Park unless that was a 'must see' for you, in which case you would need to drop some other things.

All of this is assuming you don't go to the Cape and Vineyard. If you do that you won't have time for much, if any, of Maine. You can take a whale watch out of Boston (or Cape Ann).

You still need to get back to NYC. The direct route would be diagonal across Massachusetts, in which case I'd break up the trip by stopping in Sturbridge for Old Sturbridge Village, a living history museum. The other route would be to cut across NH (the White Mountains) and into Vermont and then south from there.

As you can see, there is a lot to do and you'll have to pick and choose to fit it all in 10 days.

Here are my photos - Zenfolio | Isabel's_View | New England, Boston

This is too much for 10 days. You probably have time for Cape Cod or Maine but not both. You'd have time for a day-trip to either Nantucket or Martha's Vineyard but not both, but if you skip Maine, you definitely have time to spend one night on either island (note that it will have to be a weeknight because most of the hotels on both islands have minimum-stay requirements on weekends).

On day one you could pick up a car in NYC (or more likely at one of the airports) and drive to Mystic (about 2 hours with traffic). Spend a few hours there and continue on to Newport, where you'd spend the first night.
Spend Day two in Newport and see the cottages. You can either continue on to Boston late in the afternoon of Day 2 or spend a second night in Newport.
Day 3 is in Boston. Since you have a car, you will have to decide if you stay in a cheaper suburban hotel or perhaps something in Cambridge with cheap or free parking, or stay in Boston itself and pay up to $40 a night for parking. That's a hard choice, but if you can find a hotel on a transit line, it's definitely doable to stay on the outskirts. I'd spend both Day 3 and Day 4 in Boston itself.
On Day 5 visit Harvard. To me, it's no contest. Yale is in New Haven and could be a very short detour on the way to Mystic, but I'd skip it. Cambridge is also more than Harvard and worth exploring on its own.
On Day 6 head north, stopping briefly in Salem before continuing to Portland. Frankly, that's as far as I'd want to go. You can do whale watching in Boston or Portland just as easily as on the Cape. Then you spend the night in Portland, continuing on either Day 7 or 8 up to Freeport, where you'll spend another night. Do some exploring, spending 2 nights up there, and then drive back to JFK on Day 10 unless you are flying back from Boston. It's a serious drive from Freeport back to NYC, and you'll have to budget your full day for that and then (likely) jump on a night flight back to Europe.
The alternative is to spend Days 6 through 9 in the Cape with one night on either Martha's Vineyard or Nantucket. You'd have time to stop by Plymouth on the way out to the Cape. If you really truly want to see Salem, do it as a Day-trip on Day 6 and then head down to the Cape in the late afternoon so you arrive before dark. Or you could continue from Salem up to Portland, spend one night there, and then cut your trip to the Cape by one night, doing one island as a day-trip.

I think you'd enjoy either alternative to trying to fit in both the Cape and Maine, but that's me. I don't like driving or long days even in the summer.

There are two outlet malls between New Haven and Mystic (Clinton Crossing and Tanger a few miles further down the road); both are immediately off the road, and Clinton Crossing is the larger. Still I don't think either is as good as Wrentham, which is between Providence and Boston, so you could stop there for a few hours on your way into Boston on Day 2. There are also outlets in Freeport, and they didn't impress me all that much (unless you want to visit the very impressive LL Bean store). There are several others in Maine between Boston and Freeport, but I haven't visited them.

I'm going to sound like tomfuller, but if driving in traffic is not your thing, since you won't want or need a car in either New York City or Boston, you could take the train from NYC to Boston. When you are ready to leave Boston, rent a car to do your exploring.

Another option would be to use public transportation for some of the other sites on your list, train or ferry Boston to Salem, ferry to Provincetown then pick up the car for exploring the Cape. Do a cost/stress/time analysis and see what works best for you. In season you can also fly from Boston to Martha's Vineyard or Nantucket fairly inexpensively.

If you do take the train between NYC and Boston, note that Mystic is a stop along the route. For a public transport option to Newport, take the train to Providence and then a local bus.

For sure take a Northeast Regional Amtrak train at least as far as Mystic if not Boston. Check on renting a car in Mystic CT. Depending on how long you stay in Boston, you could take the train to Boston South Station or Back Bay and
take an Uber to your hotel and rent the car to go to all your other destinations except Mystic.
If you wanted to take the train up to Maine, you leave from Boston North station on the Downeaster train to Portland or one of the smaller stations.

Wrentham Outlet Mall for sure if your traveling the 95 corridor. It is contained whereas the Maine outlets are more a neighborhood of discount stores in mini malls.

See if your eligible for the savings passport or VIP shopper club for additional discounts. They are located adjacent to the food court.

I've driven by Clinton Crossing and Tanger but have never visited to compare.

I'd head north to Cape Anne or south to Cape Cod but not both. I'd choose Nantucket over the Vineyard as it is more manageable. Rent Scooters or bikes. Whalewatching can be from Provincetown or Gloucester in Cape Anne. Ive never heard much about whale watching on the vineyard.

Yes there is a train to Mystic, but they aren't very frequent. Many of my summer neighbors from NY take the train to New Haven or New London and drive from there. You can take metro north to New Haven from NYC, which might be less expensive.

I should also mention that there is a high speed ferry from Quanset Point RI to Martha's Vineyard. If you wanted a day trip this might work if you are staying in the Newport area.