4 days in Boston, MA...what to do? UPDATE

Immadismom

DIS Veteran
Joined
Sep 7, 2014
Messages
601
Hubby’s company is sending him to a conference in Boston in October, and I get to tag along. We will arrive early on Sunday, and leave late on Thursday. We will have a rental car. Neither of us have ever been there. What are the must-do items you would recommend? He will have most afternoons free, since he only has to attend morning seminars for Mon- Wed, and we will have Thursday morning free until we have to be at the airport by 3.

Update...we will be staying in Bedford Glen/Burlington area, hence the rental car.

Lots of great suggestions...thank you! We currently want to see the aquarium, Quincy Market, Freedom Trail, and possibly Fenway Park. On Wednesday, DH will be done by 10:30 am, so we’re going to drive to the Cape, just to see it and take in what we can. Sunday, after our arrival, we may head to the Concord area and see the Orchard House.

Any other suggestions are much appreciated!
 
Last edited:
Depends on what you like. We like history, so over the years we have walked the Freedom Trail, which is a listing of historic sights and buildings, toured the old state house, and made side trips to Salem and Plimouth Plantation. When I was there this year we visited the science museum and fine arts museum and saw the symphony. You could look into a whale watching cruise. Take a walk down Newbury Street and check out the shops.
 
Walk the Freedom Trail, it hits a lot of the historical sites. Or take one of the bus tours which hits other historical sites. Or take in a baseball game. Walk thru the Boston Common which is a very pretty park, and it’s near “Cheers” bar.

Where are you standing?
 
Last edited:

Since you have a rental car you could take a ride to Cape Cod. It's beautiful there. You could stop at Chatham Lighthouse, and drive all the way to Provincetown. There's plenty of beaches & golf, some great restaurants too.

In Boston I would go to Mooo (not a typo, 3 o's) Restaurant on Beacon Hill & you could walk to the Statehouse before dinner and visit Boston Common & the Flower Garden.
I also like the North End, lot's of history there and some great restaurants & Bakeries. My favorites are Modern Bakery, or Mikes Pastries, an Regina's Pizza. It's not your typical pizza place, I knew Ragina when I was a little girl growing up there. She used to pinch my cheeks.

Newbury Street is also a great shopping, restaurant street to visit and the Prudential Center Mall is the next street over.

Charles Street has some great shops and restaurants too.
There's History all over the city!

It's a very walkable city! Have fun
 
I would skip the Cape. Not enough time. In fact, I'd plan all activities right in Boston, except Sunday. Traffic!!!!!!!!!!
 
/
I'd keep the car in the hotel's garage for much of the time since Boston's a great walking place like many NE cities. I'd utilise the car to visit Cape Cod. Have a bit of time? Travel to the lower cape (P-Town, Wellfleet, the Truros) Less available time? Visit the upper cape which is wider and closer to Boston via a car.
 
From what you have told us of your schedule you will not have time to visit the Cape for half a day, the traffic is horrendous. Stick to seeing things in the city. The Aquarium, Faneuil Hall, walk the Freedom Trail, browse the shops on Newbury Street, take a whale watch cruise from the harbour. I probably wouldn't bother with a rental car. Parking is very expensive in Boston and you can walk or take the subway easily. Boston is a great city.
 
We did the Freedom Trail, Aqauarium and went to Quincy Market the last time we were there.
I would definitely go to the Cape Wednesday after his meeting, spend the night there and make it back to airport in time.
Since you are going in Oct, traffic shouldn't be horrendous like in the summer months.
 
Freedom Trail. Quincy Market. Faneuil Hall. Aquarium. USS Constitution. Take a Duck Tour. Eat in the north end (Italian section). Boston Commin. Shop Newbury Street. Tour Beacon Hill. Tour Fenway Park.

All of these! On our last visit, we stayed in Copley Square which was walking distance to Newbury Street, the Duck Tours, and the T stop which was easy to use. We loved the Duck Tours and we also did a stadium tour at Fenway, which I believe they do most of the year. The Aquarium was just ok for us. Did enjoy Faneuil Hall and Quincy Market. Also loved the public gardens which was close the famous Cheers sign.
 
If you enjoy whale watching, I would suggest a tour through the aquarium. We saw many whales and learned a lot. Much more of an educational outing than the Mexican tours.
 
I would skip the Cape. Not enough time. In fact, I'd plan all activities right in Boston, except Sunday. Traffic!!!!!!!!!!
Yes your probably right about this unless they go right after her husband gets out in the afternoon. It's only 1 1/2 hour drive, might be worth the trip just to go relax at the beach.
 
Sunday, when the traffic is lighter, I would go to Concord and Lexington for the tours others have recommended. There is a small museum in Concord that has a lot of Revolutionary War artifacts we enjoyed. Other afternoons you could do the Aquarium, the bus tour (hits most of the sites, you can get off and on at any site too, but I think they quit around 7).
 
Wow, lots of great suggestions here! Thank you all! I’ve been scouring Trip Advisor for ideas, and have seen many of these mentioned, but it’s hard to decide without input from folks who have been there.

I’m thinking I’d like to do the aquarium, freedom trail, ride the ducks, and Quincy market for sure. I’d love to do whale watching, but not sure if we’ll be able to fit it in.

Restaurant recommendations are also greatly appreciated! :D
 
The seaport district has tons of restaurants that are fabulous and many are right one the water with beautiful views. Temescal, Legal Seafood, Del Friscos, Strega. The north end is full of fabulous Italian restaurants...best is to wander until you find one that strikes your fancy.

Personally I would skip the cape unless you really want to go there. Head inland to concord/lexington if you are history fans. Enjoy the beautiful fall colors. Concord especially is lovely to walk around. Go to the north bridge, Walden pond, orchard house, the town center. The colonial inn is a quintessential New England spot for a bite to eat.
 
I hate to hijack the thread, but my husband and I will also be visiting Boston for the first time this year (July). I see a couple of people have mentioned Newbury Street for the shops - can you tell me a little about them? Is it mostly upscale stuff, crafty stuff, or a little of everything? Thanks!
 
I hate to hijack the thread, but my husband and I will also be visiting Boston for the first time this year (July). I see a couple of people have mentioned Newbury Street for the shops - can you tell me a little about them? Is it mostly upscale stuff, crafty stuff, or a little of everything? Thanks!
Upscale shops with a few restaurants and coffee shops
 
I work in Boston every day. My suggestion, unless you're actually planning on going somewhere outside of Boston, skip the car. You'll save yourself time, money and a whole lot of aggravation. Just about everything that has been mentioned (Freedom Trail, NE Aquarium, Boston Common, Public Gardens, Fenway Park, etc.) is accessible using public transportation (MBTA) or even just walking. Aside from the traffic in and around Boston, it's not the easiest place to drive. Streets will literally end or a one way will turn the other direction without much warning. Other than the Back Bay portion of Boston, it's not a planned city and streets sometimes seem to meander whichever way. Parking is also limited and can be quite expensive.

Personally, I don't think a drive to Cape Cod would really be worthwhile. October is far from beach weather so you wouldn't really be able to do more than walk on the beach.

I hate to hijack the thread, but my husband and I will also be visiting Boston for the first time this year (July). I see a couple of people have mentioned Newbury Street for the shops - can you tell me a little about them? Is it mostly upscale stuff, crafty stuff, or a little of everything? Thanks!
The end of Newbury Street by the Public Garden has most high-end shops and boutiques. As the street numbers go up and you get closer to Massachusetts Avenue, the shops become somewhat less expensive and a bit more eclectic.
 
Last edited:





New Posts









Receive up to $1,000 in Onboard Credit and a Gift Basket!
That’s right — when you book your Disney Cruise with Dreams Unlimited Travel, you’ll receive incredible shipboard credits to spend during your vacation!
CLICK HERE







New Posts







DIS Facebook DIS youtube DIS Instagram DIS Pinterest

Back
Top