itinerary suggestions from maine to massachusetts to cape cod
 

We (husband and I) are arriving early morning of oct 14th (thursday) and planning to rent a car at the airport and driving straight to maine. Where should we stop to visit and then to stay? We heard about portsmouth for lunch and then an inn at York Beach. What do you think? We also heard about freeport, NH to see. The next day (friday) head to boston for the day and night (mainly to do freedom trail and north end for italian food!). Saturday head off to Chatham cape cod for the day and night and most of sunday. Hopefully traffic at this time of year will not be too bad driving to the cape. Any lodging suggestions for any of these places or additional thoughts? A lot to do but we are game!

Commodore Inn/Motel-West Harwich, Cape Cod

I'd just stick with north and take in York, Ogunquit and Kennebunkport and skip Chatham. It's a lot of driving and you have so much to take in. I've been going to that area for 40 years and never stopped in Portsmouth - curious what i might be missing as far as lunch.

Thank you for the replies. I guess portsmouth is a nice town to just stop in for a bite and a rest and then continue north.

Would cambridge be worthwhile to stay in since it wouldn't be as $$$$ as boston? Easy to get into the city of boston?

Surprised that anyone would miss Portsmouth. Strawbery Banke is a major historic area, great boat trips, fun area to walk around/window shop, couple of theaters, Prescott Park for relaxing, Rt 1B is great drive thru Newcastle, (I did not enjoy visiting the sub, Albacore, but it's an unusual piece of Navy history many probably enjoy, yikes, it's small), Water Country for kids, etc. Probably best to check out chowhound for latest restaurant recommendations. When we do a day trip we usually have a lobster roll at the Ice House (actually in Newcastle) or sandwich and beer at the brewery place near Market Square. Friends recommend the Friendly Toast for breakfast.

Cambridge is fine for a place to stay. I like a hotel with view of the Charles. Nice to watch people rowing. Cab to the city or long walk to the T.

Portsmouth has tons of great restaurants and a very cute, walkable downtown on the harbor. It's a great place to stop for lunch or a longer stay.

If you're interested in Maine, I'd probably stay in Kennebunkport or Ogunquit.

What is the length of your trip? Where are you coming from? It sounds like you are arriving on a Thursday, driving to Maine for one night, then to Boston for one night, then to Cape Cod for one night. I agree with LittleWing - just stick to one area, either Boston and Maine, OR Boston & Cape Cod.

I would drive to Portland, maybe with a stop in Portsmouth for lunch, and then head straight to Portland & spend 2 nights there. It's a great city with a nice old port area, art museum & lighthouse. Then you could slowly drive back to Boston & stop at Kennebunkport, Oqunquit and/or York & spend your last night in Boston. Sounds like you are returning home on Sunday? With this itinerary you see the southern Maine coastline, Portland & a little of Boston.

Or you could head to the Cape when you arrive in Boston, spend 2 nights in Chatham, visit the National Seashore beaches, take easy hikes, rent bikes, etc. We like to stay at Inn at Duck Creek in Wellfleet. Then drive back to Boston & stay overnight for one night.

Grumpeon,

That weekend will be the Wellfleet Oyster Fest in Wellfleet on Cape Cod. It's a popular event on a nice weekend so you may either want to go or, if not, avoid downtown Wellfleet that weekend. It also means that hotels/inns in that area may book up early.

Also, you may not save money by staying in Cambridge, it's not necessarily cheaper than Boston for a good location. If you do stay there, try to be near a red line train stop for easy access into Boston.

Great responses! So helpful. We are in california and have never been to the new england area. Yes, I am understanding that maine,boston and cape cod is too much to see and drive. We are out for some R&R but driving along the coast and without children sounds nice to us. Looking forward to maine seafood!!! Leaning toward maine and boston. Any other thoughts are welocomed and appreciated!!!

Hi There,
We did this trip 2 years ago and now planning a second. Loved every minute. Here was our route..Flew into Manchester drove to Cape Cod. We stayed at Anchor Inn (lovely) and went to Martha's Vineyard. (Disappointed a little in MV but glad we went there to see it)Next to Boston.
We did Boston in two days, the Freedom Trail and plenty of Italian places to eat. We stayed downtown very easy to get around. We did the city tour, hop on, off great way to see the city and then use for transportation. Next to Portsmouth. It is a cute litte town with a nice little shops. We ate at a very quaint seafood place and it was a perfect lunch stop. We stayed the night in Kennebunkport. Ate at Mable's seafood. Wonderful. Drove through Franconia Notch State Park in New Hampshire. We also went to Vermont stayed in Stowe. We moved around every night but had a ball. Have fun.

I am so glad you have chosen to stick with Boston and one area.

Be aware that the "coastal rt", Rt 1 in ME, isn't really on the ocean although there are a few small sections of Rt 1A NH and southern ME that are beautiful. Because the NE coast is so jagged, you have to go down dead end peninsulas off Rt 1 to get to the ocean. It isn't like 101 along the CA coast. Rt 1 itself is mostly very "strippy" and not scenic at all. Factor this in to your schedule.

Thank you all so much! Good to know that the east coast drive is not really along the ocean. People keep mentioning oqunquit,ME and kennebunkport. Should we skip York and go for these stops instead? When we go to Boston, can someone tell us some cities to stay outside of boston but convenient to the "red" T so we can get into boston?

Dreamtravelers your itinerary sounded great!

What's your hotel budget for Boston?

The Red line served Cambridge and the Green line's various branches serves Brookline and Newton. At the end of the Riverside (green) line is the Hotel Indigo, which is right off Rt. 95 (128), but about an hour's commute into Boston.

Brookline has a Courtyard Marriott and a Holiday Inn. The commute from there is much shorter and both hotels are in/near Coolidge Corner, which has lots of shops and restaurants.

Check out the Midtown Hotel in Boston--they often have reasonable rates and are located near the Prudential Center.

I think Ogunquit and Kennebunkport are more charming than York, which is why they are mentioned more as stops. But if you're heading up Rt. 1 in Maine you'll go through or near all of them and can take get off the main road and explore.

Start checking hotel rates around Boston as you might be hitting some college "parents weekends" or fall fests clogging up hotels along with tour buses full of leaf-peepers.
For comparison, your idea as I understand it is basically like flying into LAX, driving up to Santa Barbara for a night, then driving back down to LA for a night, then off to see San Diego for a night, then back up to Los Angeles for your flight home. Not a lot of time to experience much except the traveling.

It sounds like you'll be in Boston over the Columbus Day weekend? It's the peak of tourist season for all the leaf-peepers, just so you know.

Why the Red Line of the T? Why do you want to stay outside of the city? I assume you'll return your car when you first return to Boston? There's no need to keep a car IN Boston.

I don't see any reason why you would want to stay outside of the city, unless budget is a concern. If you tell us what your hotel budget is for Boston, we can make more recommendations.

We were shooting for $150-200.00 a night for a hotel. We really aren't going to be lounging at the hotel so we didn't want to pay much for it. Rather pay more in Maine since we will be there longer. Any lodging ideas in or around the boston area to fit our budget? I read about the John Hancock Hotel which had a reasonable rate. It seems to be in a good location. Thoughts.....

I'd at least look to see if you can find something that fits your budget IN the city, before staying way out in the suburbs.

Other budget options are:
Park Plaza Hotel
Hotel 140
Harborside Inn
Constitution Inn
Residence Inn Tudor Wharf
Hampton Inn in Cambridge
Holiday Inn Express & Suites on Friend Street
John Jeffries guest house

Or, you can always try Hotwire, though it may be a little too soon to get a good rate.

The John Hancock Hotel is a good reasonably priced hotel. It is used often for conferences. The rooms are not large but they are fine. There is no restaurant or bar but you're located next to Copley Square so there's no problem finding places to eat. If you can get it for a good price, I'd go for it.

Thank you so very much to everybody!! Last question, is it feasible to go to Newport,RI to see vanderbuilt's mansion for 1/2 a day and then back to Boston? Is it worth the effort?