Sbhill895

My Husband and I and two teenage sons are planning a trip to New England area August 7-August 17
flying in and out of Boston. We based the trip on getting Red Sox tickets so we will be spending the 14th-17th in Boston. That leaves us from August 7-14 to explore outside of Boston. We have a friend in the area that suggested some "must see's" in the area but my question is what is the best way to do all of this? These are some spots he suggested....

"You would definitely enjoy Maine (particularly Kennebunk and Portland which are in Southern Maine). In Kennebunk there are some nice B&Bs. I don't suggest going deep into Maine but Bar Harbor/Camden is very nice along the coast, but the inner part of Maine is just hundreds of miles of the same thing over and over.
If you stay in Portland, the Hampton Inn is your best bet. Nice hotel and in the middle of everything. You can take a ferry and bounce around all of the islands just off the coast of Maine. Lots of good restaurants near the hotel.

Nantucket/Martha’s Vineyard
Likewise, I would think Nantucket and/or Martha's Vineyard is a must see. You can do that as a series of day trips, or spend a few days out there. Martha's Vineyard is the easier to get to of the two spots, and better for a day trip. There are ferries that leave from New Bedford, Falmouth, or Hyannis depending upon where you are coming from. We love the Edgartown section of Martha’s Vineyard. Great striper fishing off the island!

Newport RI
Newport RI is also really cool. You can charter a sailboat (and crew) and tour around http://www.sightsailing.com/ and tour the famous mansions on Bellevue St. http://www.newportmansions.org/

Cape Cod
You will get a lot of beaches/sand in Martha’s Vineyard/Nantucket/Mattapoisett/Maine/Newport, but Cape Cod has the traditional shore feel. There are a ton of beaches and quaint towns. Chatham has cool beaches, shopping, restaurants, and good fishing too. There is an island (right off the coast of Chatham)."

Okay so those were his suggestions and this all sounds wonderful, but I am overwhelmed as to the best way to do it all ( by car, ferry, staying a couple days in each spot? ) I would love some suggestions and input! Thank You!!

NewbE

We just did exactly this kind of survey trip, staying a couple of days each in Boston, Newport, Portland and Chatham, but it involved quite a bit of backtracking by car (for various boring reasons), so I wouldn't offer my itinerary as a model.

The two main problems are:
--having to return to Boston for your flight out. Since your flights are booked, what's done is done.
--wanting to see Newport, which is south of Boston and therefore not on the way to anything. I would reluctantly suggest dropping it from your itinerary, unless the Gilded Age mansions and colonial town appeal to you particularly. (We enjoyed it very much and are glad we went, backtracking and all.)

Others here offered better itineraries for me, and I'm sure they will for you, too. So I'll just offer a few notes.

Chatham makes a great base for exploring the Cape, because it's in the middle, and is a very nice little town. I would recommend spending a few days on the Cape, if you decide to do it, because the pleasure is just to walk the trails, enjoy the beaches, eat the food, poke around the towns, etc. (Accommodation may be tough to find anywhere on the Cape at this late date, though, as your trip is during high season.)

Portland is a gem of a city and out favorite "find" of the trip: it's compact, atmospheric, a wee bit gritty, foodie, artsy, and well located for exploring. Definitely take a ferry to one of the islands while you are here. I can suggest restaurants if you end up staying in Portland.

I think Bar Harbor is too far to go on a trip of this length.

So perhaps three nights in Portland, the rest on the Cape, then to Boston for the final few?

Rent a car at the airport on arrival and drop it off in Boston on your way in. You won't need it for the last few days of your trip, and paying to park it would be silly.

Sbhill895

Oh thank you so much NewbE!! That helps a lot! We are using points for our flights...We definitely need to return from Boston, but if we could change where we fly to upon arriving, would that make more sense or would that help us in getting to see a bit more?

Sbhill895

Oh and where did you stay in Portland? A house or hotel?

NewbE

We stayed at a hotel in Portland, the Press Hotel, which we loved! It's brand new, for one thing, and very well located. Its design is very cool, as it's a former newspaper building.

Others here recommended an open jaw itinerary in order to avoid driving to and from Boston--it's not far, really, just tedious. So it might make sense for you to fly into Portland and out of Boston.

Nikki

You could fly into Providence, stay in the Newport area for a couple of days and then drive to the Cape for a few days before driving to Boston and returning the car. This way you wouldn't get to Maine, but you would get to Newport.

Fra_Diavolo

With the amount of time you have, I would recommend picking either Maine or the Cape. While you could visit all these places in a week, you would be very rushed.

I think Maine has the most beautiful coastline in the east (if, like me, you love granite, pines and the sea). On the other hand, the water is very cold, and sandy beaches are in short supply except in the southern region. A few days in Camden, a few days in Portland, and it's time to head for Boston. What to do? Well there's hiking, small museums, scenic villages, boat tours and course, lobster.

Choose the Cape if you'd rather be swimming, although all the above activities are also available. I do think Chatham is a good base. You're near the National Seashore, can easily get to Provincetown and should easily fit in a day trip to Nantucket or MV. There is a permanent gray seal population in Chatham, which might sound appealing, but they bring in Great White sharks, so the beaches may sometimes be closed.

You could also add a side trip to Newport without going to far out of your way, either coming or going.

You may find lodging availability very tight at this late date. Once you decide, make your reservations immediately.

Sbhill895

Thank you all so much for your replies and input! It helps a lot��

travelgourmet

With the amount of time you have, I would recommend picking either Maine or the Cape. While you could visit all these places in a week, you would be very rushed.

Agreed. I view the Southern Maine Coast and the Cape as similar types of destinations.

clarkgriswold

Maine needs to be booked a.s.a.p. for August and the cancellation policies are quite strict, ie 30 days in advance. I would also book a car sooner rather than later if you're planning a road-trippy vacation for the 1st 7 days (probably won't want the car while you're IN Boston).

Do you have a budget per night per room, and do you need 2 rooms or are u looking for 1 room/2 queen beds?

cw

What do you want to do during the 7 days? Hike, sit on the beach, shop, see sights, etc.? Knowing that might help in advising you.

I agree with comments above. Choose either the Cape (side trip to Newport) or Maine.

Make reservations as soon as possible for the weekend. During the week, you'll have more flexibility on where to stay.

NewbE

Given that we did we did Boston, Newport, Portland and Cape Cod in 8 days, I think 7 is plenty for just Portland and the Cape. I did not find the areas very similar, nor the coastline. But of course it all depends on how much just-hanging-out time is wanted.

dfrostnh

What would your teenage boys like to do? You could also include a stop in Portsmouth NH - educational visit to Odiorne Point science center, visit the Albacore sub, music/theater event in Prescott Park, Strawbery Banke Historic Area. We enjoyed the mailboat cruise of islands in Casco Bay mentioned above. You can park in the parking garage next to dock and then leave car there after you get back while you explore Old Port Area (ice cream lovers should make sure to visit MDI ice cream). Duckfat for French fries.
But, you can also do harbor or inland river cruises from Portsmouth NH. These have narration (not a lot of narration on mailboat, it is a working boat, but enough). We have not been on a gundalow cruise but they look interesting http://www.gundalow.org/

If your family is interested in classic cars and planes, Owls Head Transportation Museum near Rockland ME could be a day trip from Portland. Special events on weekends make the visit even more interesting. I really didn't think those antique airplanes could still fly!

If you want some rocky hiking without going all the way to Bar Harbor, you might try Monhegan Island. We took the boat from Boothbay Harbor. I strongly suggest taking a picnic lunch.

Also, check Portland info for baseball games.

If your family wants beach time, southern Maine beaches should be fine. Our family used to like York Beach and walking to Nubble Light and the arcade area.

Ackislander

You can easily do a day trip from Hyannis to Nantucket, either on the Steamship (SSA) fast ferry or the Hy-Line fast ferry. The Steamship is a bit cheaper and almost always on time or early. The Hy-Line is a bit more casual. Both get you there in about an hour, and both drop you off downtown. The Steamship drops you near the Whaling Museum, the Hy-Line drops you off at the foot of Main Street.

You absolutely positively do not need a car on Nantucket, and a good thing, too, since it would cost you north of $500 to bring one with your family.

If your boys are interested in the beach and find history and architecture deadly, there is a beach bus that leaves from right in front of the Whaling Museum. Food and toilets are available at both Jetties Beach and Surfside Beach.

I hope you will walk around more of the historic town and spend less time looking in shops than many visitors do. Walk up Main Street beyond the Pacific Bank to see the houses that wealthy shipowners built in the 1830's and 1840's. Turn left on Pleasant St at the Three Bricks, identical mansions built for his sons by a wealthy merchant, identical so they wouldn't argue. Take the second left off Pleasant and wander around a maze of tiny streets and charming houses. Find your way back to the center of Town and have lunch. After lunch, go to the Whaling Museum and the Atheneum. You can shop or you can sit on the edge of the harbor on Easy Street and watch the boats come and go.

Or you can call Gail's Tours and see a lot more of the island in her Mercedes Sprinter.

Meet the boys, head for Hyannis, and stop at Cooke's Seafood on Iyanough Road (Rte 28) for fried seafood before returning to your hotel.

Your week is Race Week in Nantucket, and the harbor will be packed with incredible sailing boats and the giant yachts of those who come to follow the races. It is a great time to come.

Sbhill895

Thank you again for all the amazing replies and input!! This helps us out so much. This is my first time to use Fodor's forum so this has been very helpful!!

HappyTrvlr

With teenage sons, I rhink you need to drop the idea of Newport. I doibt they would be theilled touring Gilded Age Mansions. I enjoy foing there but not with kids.

Inakauaidavidababy

Hey HappyTrvlr --- are you suggesting it was the woman folk that built the Guilded Age Mansions? And the manfolk were not interested?

clarkgriswold

Yeah that's exactly what she was suggesting eyeroll