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August Vacation in Boston: Any Suggestions?

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In a few weeks, I will be traveling to Boston to take a short break from everyday life. A. and I will be driving up to Boston by way of Newport, Rhode Island to do some sight seeing, relaxing, and enjoying a bit of New England.

So far, we have plans to tour a few of Newport’s mansions, walk the Freedom Trail, see Blue Man Group, and hang out in the hotel’s pool. A. says we must visit the Public Garden to paddle on the Swan Boats. I’m sure we’ll make our way to Faneuil Hall and Quincy Market at some point; we’ll have five days to make the most of the vacation.

As far as the hotel goes, I did some shopping around to find something not more than just a few miles out of the city for a reasonable price. The best deals were 30 miles outside of the city, a little bit farther than we would have liked for going into the city four days. We settled for paying a little bit more to stay at a hotel less than 6 miles from downtown. After comparing the prices offered by a number of websites, I called the hotel reservation line to get a better rate than what I could find online. The magic words in this case were, “Triple A.”

Any Bostonites have some suggestions for more things to do?

Updated October 9, 2016 and originally published July 21, 2007.

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About the author

Luke Landes is the founder of Consumerism Commentary. He has been blogging and writing for the internet since 1995 and has been building online communities since 1991. Find out more about Luke Landes and follow him on Twitter. View all articles by .

{ 20 comments… read them below or add one }

avatar 1 Anonymous

You may want to go to the “Top of The Hub” restaurant, at the top of the Prudential building. The restaurant give’s you a bird’s eye view of Boston from all vantage points (at 55 stories up). The place ain’t cheap, and there’s better food to be had. But, stop in for a drink and enjoy the scene.

Afterwards, enoy the Newbury Street scene – pricey, but worthwhile. Of course, strolling around doesn’t cost anything.

Also, if you’re a Jazz fan, the best place to go is: Wally’s – on Mass. Ave. Not exactly the best part of town (go by cab, and get out by cab), but the place is hot!

Bleacher seats at Fenway Park can’t be beat. And they’re fairly cheap (for a major league stadium).

Go to the North End for some of the best Italian fare around.

Lastly, The Isabella Stewart-Gardner Museum (in the Fens section) is a very unique experience.

Have fun, and don’t forget to Pahk ya Cah in Hahvahd Yahd.


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avatar 2 Anonymous

before or after walking around the public garden, or as a pit stop on the freedom trail, walk around Beacon Hill for some quaint, European-esque charm – and some of the most expensive property in boston!
I’m also partial to the JFK library & museum just south of the city via the red line train and then a shuttle bus – right on the water with pretty views of the skyline.
On the opposite end of the red line is Cambridge & Harvard Square, always interesting to explore.

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avatar 3 Anonymous

Just came back from Boston. Park your car take the T to where ever. The walking Freedom Trail tour was worth the $12. The Trolley tours were only as good as the driver. In one tour we had 3 drivers. First was OK he lasted 10 minutes the next had an Israeli accent hard to understand and the last was a true Bostonian. He was good.


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avatar 4 Anonymous

I’d definitely suggest leaving your car at the hotel and use the MBTA to get around. If you like authenticItalian food, make sure to visit the North End. Abruzzo’s is great –

If you want to escape for a day, check out George’s Island

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avatar 5 Anonymous

The Duck tours are fun — they drive around on land, then head into the water. Boston Common, Fenway Park … there’s a lot to see.

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avatar 6 Anonymous

One more vote for eating in the North End. Our favorites are Monica’s Trattoria on Prince Street and Marco’s on Hanover St. Marco is a bit more expensive but they are both great.

I would also suggest getting a nice map that fits comfortably in your pocket. It is easy to get lost in Boston and you’re going to be walking everywhere.

In the spirit of your blog, here are some cheap suggestions: When walking around the public garden, there is a great little grocery store called Deluca’s on Charles Street. You can get a very nice lunch for little money. They have great sandwiches. Next to the park is Beacon Hill which is very nice, I would suggest walking up Acorn Street. It is bit of a hidden gem.

Walking along the Charles River is quite nice as well. There are free movies on Fridays at the Hatch Shell by the river – you should bring a blanket to sit on.

I’m not sure when you’ll be here, but there is Shakespeare in the Park in August.

Okay, one last thing… you will be using the T (the subway) quite a bit. I would highly suggest getting a Charlie Card. You can order them online from the MBTA website preloaded with money. ( The Charlie Card will make you look like a true Bostonian and you will be saving money as well.

Okay. That’s enough for now. Have fun!

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avatar 7 Anonymous

I am not giving you any advice but feeling jealous about your trip :)

I liked your idea of getting some help from the people who already visited or living in that area.

Music will be a plus in site seeing.

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avatar 8 Anonymous

I’ll second the recommendation of the duck boat tours–it’s an amphibious vehicle that tours Boston and the harbor. The drivers wear costumes, and are always engaging. With these you’ll much MUCH better tour of Boston than you’ll get through the trolleys, IMO.

You will probably want to book reservations in advance, though–there’s usually quite a line.

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avatar 9 Anonymous

Like everyone else said, don’t bother driving in the city. Parking is expensive and driving around is a hassle with the terrible streets signs and the names of the some streets sometimes changing every few blocks. You can get a weekly T pass that will allow you unlimited rides on the buses and all subway routes. And if you don’t want to do that, I agree with the above and say get the Charliecard, it’ll save you $.30 on entrance.

Mike’s Pastries in the North End is good for dessert, plus you can walk around the waterfront which is nice.

the new Institute of Contemporary Art is supposed to be nice, and the Museum of Science is pretty good.

For the trendier areas, go to Newbury Street and the South End. The South End has some sketchy areas, but also nice ones. And if you want a nice dinner, I’d suggest Sibling Rivalry. ( two brother chefs that compete with their dishes. really good, a bit pricey, but worth it.

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avatar 10 Anonymous

Okay, a couple more things:

West of Boston is the DeCordova Art Sculpture park and musuem. It is a very nice place and would be a great break if you get tired of the city.

The Institute of Contemporary Art (ICA) in the last year or so has relocated to a brand new building on Boston Harbor. It is a very interesting building and the museum is quite nice.

Also, don’t forget about Cambridge. Harvard Square is quite lively. And if you’re into folk/acoustic music, I would highly suggest seeing something at Club Passim in Cambridge. It is a very small place and they have music every night.

Another great neighborhood to check out is the South End. There are a ton of great restaurants. Do not confuse the South End with South Boston.

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avatar 11 Anonymous

Spend some time at the Gardner Museum – and absolute gem!

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avatar 12 Anonymous

Hi Flexo,

If you are going to try your luck getting Fenway Tickets or just want to take a tour of Fenway be sure to stop in at Boston Beer Works and try the Blueberry Beer.

As others have said, taking a tour is a great way to get oriented in the city and see most of the historic highlights and landmarks in a short period of time. I agree that Duck Tours are the best option (although also the most expensive). However, if you prefer discovering the city yourself and at your own pace download these Freedom Trail Audio Tours and pack your iPods and comfortable walking shoes.

Two of my favorite local attractions that tend to get skipped or overlooked by visitors are:

USS Constitution – Many folks skip the Charlestown section of the Freedom Trail because it requires a long walk from the North End on a fairly desolate bridge to reach the Navy Yard. However, the tour of Old Ironsides (USS Constitution) is free and the tourguies are great – and it is the real deal old warship – something not to be missed in my opinion.

Isabella Stewart Gardner Museum is the other often overlooked attraction. With the amazing Boston Museum of Fine Art steps away, the Isabella tends to get overshadowed. However, it will be a nice compliment to the Newport Mansions you plan to tour – here you will see a city mansion adorned with art (and get to see the place of the now most famous unsolved art theft).

Hope these tips help. Enjoy your visit to Boston. It is a small and walkable city – but it is so packed with places to see and things to do your four days will fly by!

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avatar 13 Anonymous

I ditto the comments on the Gardner Museum and the Museum of Fine Arts they are right around the corner from one another – The Trolley Tours or the The Duck Tours are a fun way to see the city (1 if by land 2 if by sea – ha ha :) . Harvard Square in Cambridge is worth checking out as well – lots to see and do! – Hope you have a great trip. I enjoy your blog a lot!


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avatar 14 Anonymous

Visited Boston in June and enjoyed the Adams historical site in Quincy. Try lunch or dinner at the irish pub “The Holy Ground” on Hancock Street in Quincy.

Also the T operates a ferry from downtown Boston to Charlestown. Great views of the harbor and docks next to the USS Constitution. Get that Charlie Card!

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avatar 15 Luke Landes

Wow. Thanks for all the suggestions, everyone. Keep them coming! We looked into the Red Sox already — they’ll be on the west coast. We would have liked to see a game.

The museums sound great to me.

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avatar 16 Anonymous

If you are looking to get some exercise, you should check out the Bunker Hill monument. Lots of stairs to go up and down. The Duck Tour was fun and you can’t go to Boston and not see the USS Constitution. I agree with the other people about the North End, lots of good Italian there, I can’t remember the name of the place I went to a few years ago. I think Newbury street has some good places to eat outdoors if you want that kind of vibe too. Hope this helps.

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avatar 17 Anonymous

I second the Top of the Hub. There’s an observation deck if you want to skip the restaurant.
I used to find the Prudential Center a useful landmark for getting around. I could locate it from most neighborhoods and know where the Back Bay was.

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avatar 18 Anonymous

Isabella Stewart Gardner Museum rocks.

More suggestions:

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avatar 19 Anonymous

If the Sox are on the West Coast, you can still take a tour of Fenway some days. Worth it if all you’ve seen is on TV.

Giacomo’s in the North End (or South End) is good Italian with an emphasis on seafood. Huge portions, good prices, both for food and wine. There will be a line in the N.E., but it moves fairly quickly and is worth the wait.

Mike’s Pastry is usually jammed, you might try Modern up the street. Just as good.

I second most of the rest of the list: If you have a car the Peabody Museum in Salem is nice and Salem is the typical New England coastal town.

The MIT museum is small, but quirky and worth the trip if you’re on that side of the river.

The South End and Beacon Hill (Charles St.) have lots of quaint, quirky shops.

I’d suggest picking up a Boston Phoenix or Improper Bostonian when you get to town (both free) to check out any other special events in town.

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avatar 20 Anonymous

I second the duck tour…I took a ten day trip to Boston a couple of years ago and it was recommended as a good touristy thing to do. It was well worth the money spent. I saw a lot of things I wouldn’t have otherwise seen, and it gave me ideas of areas I wanted to go back and explore later on my own.

Definitely a good time! We bought our tickets right away at the start of our trip as we’d been told they sell out. Apparently you can’t just typically walk up and buy a ticket for the next tour. You may be able to get them online, too.

We also ran across the street the morning of our tour to Dunkin’ Donuts and got a box of donut holes to eat and share with our tourmates. Good way to make friends! :)

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