Summr 2017: Boston-Maine-Martha's Vineyard
 

Hi!

I am looking for New England experts to critique my preliminary itinerary for a New England road trip my mom and I are taking in July 2017. FYI- I am in my mid-20's and this trip is for my mom's 60th birthday. She is very active and in great shape, so I know she will not have a problem keeping up with some of the more active things I have planned. We are going to fly in to Boston from Chicago and rent a car for our trip. We will spend time in Boston at the end of our trip when my dad will join us for the last few days. Any changes/advice is appreciated! Please let me know if I am overlooking something important. I would also welcome any recommendations for Martha's Vineyard- I haven't spent much time planning that part yet.

Day 1: Arrival >> Portland (2 nights)
Early flight into Boston
Rent car and drive to Portland w/stop in Salem along the way
Salem, ~1hr for Hocus Pocus walking tour
Arrive in Portland, check-in to B&B or air bnb

Day 2: Portland
5 Lighthouse Bike Tour
Explore town/shops on Congress St.
Walk East Prom trail and Back Cove trail

Day 3: Bar Harbor (3 nights)
Drive to Bar Harbor (~3 hrs)
Walk the Shore Path
Explore shops

Day 4: Bar Harbor
Rent bikes and ride on Acadia carriage roads via Bicycle Express from Village Green
Tour Atlantic Brewing Company

Day 5: Bar Harbor
Take Island explorer to Sand Beach- Hike Ocean Path, passing Thunder Hole & Otter Cliff, then to Jordan Pond area
Sunset whale watching cruise

Day 6: Martha’s Vineyard (2 nights)
Drive from Bar Harbor to Woods Hole ferry station (~6hrs)
Ferry to Martha’s Vineyard
Check into air bnb

Day 7: Martha’s Vineyard
Ride bikes from Vineyard Haven to Oak Bluffs to Edgartown
Ferry to Chappy Island?

Day 8: Boston (3 nights)
Ferry back to Woods Hole
Drive to Boston
Stop in Plymouth on the way, Plymouth Rock, Mayflower
Return rental car
Check into hotel

Day 9: Boston
Brunch at Paramount in Beacon Hill
Explore Beacon Hill neighborhood (Visit Cheers, shops on Charles St.)
Freedom Trail tour
Explore North End area & have Italian dinner

Day 10: Boston >> Home
Boston Public Garden
Explore Newbury Street
Fly home

excuse my poor proofreading!

The best of Salem (IM local O) is the PEM and the town's architecture, not the tacky witch stuff.

Plymouth Rock is disappointing, not worth even the time finding a parking space. Plimouth Plantation is a must see if in the area. They even know of it in Sweden at a similar historic recreation village there.

I agree with SambaChula on the Salem and Plymouth visits. In Plymouth, the replica of the Mayflower should be back after some restoration at Mystic Seaport. We were at breakfast on the Mystic river and saw it being towed from the seaport on its way back.

You also need to be aware that lots of things can affect your driving times. Depending on the time of day, weather, bridges over the canal, phase of the moon, etc. getting from Bar Harbor to the ferry in Woods Hole can take much more than 6 hours. Also if you do not have a reservation for your car, parking is away from the ferry landing and there is a shuttle that takes you to the boat, so add at least 15 minutes for that.

In Bar Harbor be flexible if the weather does not cooperate, have a plan B.

I generally like your itinerary. I'd skip Cheers in Boston, but I suppose if you're walking by anyway, you can stop in. It's a tourist trap. Consider the free tour of the State House, since you're going to be in the area. It's not too long and is interesting.

Plimouth Plantation might interest you as a stop from the Cape to Boston.

Try to time your driving to avoid rush hours and rush time back and forth from the Cape. Friday nights, Saturday mornings and Sundays are bad.

As others have mentioned, it's important to know what days of the week you are traveling, especially day 6. 6 hours from Bar Harbor to the ferry is optimistic. (Once we get into July, check driving time on the same day as next year.)

Are you planning to take your car to MV or rely on bikes and public transportation while there.

If you are bringing your car, I'd reserve a spot way in advance, but for only two days you probably don't even need a car.

We are not planning on bringing a car. We're big bikers so we'd rely on biking and public transport.

Nthing travel times: your travel time from Bar Harbor to Woods Hole is very close to impossible on Friday because of traffic south of Boston and very difficult on Sundays because of traffic returning to Boston from Maine. The tolls can take forever, and all you need is one accident ahead of you.

I also agree on Salem. The Peabody Essex Museum is full of artifacts, not just pictures, they own a real Chinese compound, and they own at least three early American houses that you can visit with a guide. The witch stuff is either looney or tatty.

The drive from Bar Harbor to Woods Hole will most likely be on a Wednesday, so hopefully it won't be too much of a problem. We are prepared for it to take longer than 6 hours. We will view that day as not much more than a travel/getting settled in day. Any other suggestions?

I would try to get through the Boston area before 4 p.m. on day 6, ideally before 3 p.m. to give you less traffic going South to the Cape.

When you return to Boston, Cheers on Beacon St. is a photo op from the outside. They did build a replica of the TV set at the Cheers Bar in Quincy Market. The Public Garden is across the street.

Do you know already where you are staying? The Paramount does get pretty crowded on weekends--go early.

I recommend michelle topor's north end food tour. Very interesting and visiting shops for samples is fun.

Agree with visiting pem or skipping Salem.
I would substitute Portsmouth NH. Time lunch on drive to Portland to stop someplace good like waterman's for lobster. Moght be too far out of the way but do go thru camden and drive to tje top of mt Battie.

I would skip Salem and Plymouth. Plymouth is a nice town to visit but not worth the trip. Plymouth Rock is small and caged and takes up all of 5 minutes. The mayflower tour is not my cup of tea and I wouldn't recommend it. As for Salem, the tour I would consider is a bit cheesy. Again, if these really interest you go right ahead but I think it isn't quite worth the extra time. If you have extra time I recommend Newport, RI and doing the cliff walk and touring some historic mansions. Too cool!

Thanks for the feedback! We will skip Plymouth for sure but will likely still do Salem (I am ok with cheesy from time to time). :)

We would love to fit Newport in but not sure where. Would we have to add another day? My mom really wants to do Martha's vineyard and I don't want to cut bar harbor short.

The basic framework, with tweaks for traffic realities sounds fine. Salem is not on the way to Portland - it will take at least 30-45 minutes off I95 to get into Salem with traffic, which is always. And there is zero chance you can make it from Bar Harbor to Woods Hole in 6 hours. I seriously might allow 10.

Plymouth Rock is funny. It is a boulder in a mesh cage on the coast. There is a plaque signifying that it is Plymouth Rock. I seriously think some contractors found any old rock and put it on display. Mayflower II feels like a middle school class trip. But it is not much of a detour off your route, so your choice.

Enjoy your trip - all your destinations are among my favorites in New England.

Newport would probably take another day just because there is a lot to see. If you are able to do that though I thin it would be a great addition to your vacation! You can spend all day touring mansions (look into that ahead of time) and walking the cliff walk and when you are done there are plenty of oceanside restaurants and cute shops! If you can I recommend Castle Hill Inn. It is a bit pricey but you could just go for drinks if you want. They have a huge lawn overlooking the water and boats

Two days on Martha's Vineyard? You won't want to leave.