Where should I vacation this August? Charleston, Chicago, or Boston... Please help!

[TexanMinnie]

Hi Everyone,

So, my boyfriend and I want to take a trip in mid-August and have narrowed it down to 3 places. We are trying to decide between Charleston, Chicago, and Boston. We love good food, history, live music, breweries, distilleries, bars, and also being outside. We have not been to either of those cities and am hoping that y'all can help us to narrow it down to one place. Can you tell me your favorite attractions, favorite places to stay, safe sides of town to stay, and also any favorite bars or restaurants with great food?

Thanks so much!

 

[TexanMinnie]

Oh, I should add... I have already looked up the main attractions in each city. I just want to hear from those who have been or live there as I wouldn't want to add something that isn't worth visiting to the list of "Must Do's". Thanks!!!

 

[mrs. magoo]

We have done both Boston and Chicago in the past 5 years. I vote for Chicago. We loved it and we were only there 3 days. We drove from Western NY to Cleveland for a ball game and then stopped at Notre Dame on our way to Chicago. In Chicago we did so many things. We loved and I mean loved the architectural boat tour. We used the hop on hop off bus to get to so many attractions. We ate deep dish pizza and Genos and overall had an incredible 2 days. We also liked Boston and there is more history there. We did the freedom trail and a duck boat tour. We also went to the aquarium. We loved Salem as well. They are both great choices. Both will be hot in the summer. I was to Charleston as a little girl so I have no real memories but it will be extremely hot and humid in the summer. I want to go in the fall when I revisit it.

 

[Kitty 34]

Chicago

 

[mjkacmom]

I would eliminate Charleston due to weather, moving dd into college in NC in August and dreading it). I’d go with Chicago.

 

[a1tinkfans]

Boston! Awesome

 

[Skippyboo]

I would say Boston or Chicago.Charleston is nice but it’s going to be super hot and humid in August. Weather that you don’t want to spend a lot of time outdoors in. Never been to Chicago but have been to Boston. Lots of colonial history there, JFK Presidential Library nearby Salem is cool

 

[izzy]

As much as I like Charleston, it will be miserable there in August given the high temps and oppressive humidity.

I would do Boston or Chicago. If you go to Boston, be sure to eat at one of the great Italian restaurants in the North end. And visit Mike’s Pastry. Yum!

 

[JimMIA]

I'd go with Boston as well, and also with all of the recommendations by @mrs. magoo above. Freedom Trail takes you to Paul Revere's house, Old North Church (don't miss the gift shop there), and lots more. Depending on the weather and conditions, you can also do whaling tours from Boston. I would add MIT and Harvard, a ballgame at Fenway.

For dining in Boston, we usually go to the Union Oyster House, which is right near Faneuil Hall. It's the oldest continuously-operating restaurant in the US. They've been in business for almost 200 years (est. 1826), and they've only had 4-5 owners.

From the Faneuil Hall/Aquarium area, you can also walk up to North End for some great Italian food. And I would add Boston Common, and while you are there, the obligatory visit to the real Cheers. Gotta have a set of Cheers beer mugs -- but get them from the real cheers, not their satellite place in Faneuil Hall.

The on/off bus tours are not cheap, but they are a great way to see most of Boston is a relatively short time. I got off one time to see Old Ironsides, and to my delight, the US Air Force Academy Choir was part of my tour group. They did two short concerts during the tour, and it really added a nice flavor. Another interesting stop we did was the Boston Tea Party museum.

You can do some deadly shopping on Newbury Street.

And in addition to the mandatory beer at Cheers, you also MUST have some lobsta and multiple bowls of chowdah.

SO much to see and do in Boston. We liked Chicago too, but we love Boston. We have relatives there, and also on the Cape, but we never get tired of Boston.

If you have enough days, you might consider a trip down to Cape Cod. If you go to the Cape, I'd stop at Plimoth Plantation. It's a restoration of a colonial village, and an interesting couple of hours.

 

[JimMIA]

For lodging, we can stay with relatives, but we prefer to be in the Faneuil Hall/waterfront area. Last time, we stayed at the Hilton Faneuil Hall, which was good. The Marriott Long Wharf is also very nice. Both are very centrally-located to the things we want to do.

If you want to be in Back Bay, as opposed to the more historic area, there are a number of hotels in the Prudential Center area.

The other dining that we really enjoyed last trip was Ruth's Chris. I know it's a chain, but this one is in the old Boston City Hall and it was exceptionally good. Best meal we had, actually, including Union Oyster House.

 

[Cindy's Mom]

Chicago is an amazing city, especially in the summer. If you're coming in August, just be mindful of the Lollapalooza dates, downtown is INSANE that week.

 

[unrequited23]

Are you driving or flying? How do you feel about public transportation? If you are flying and public transportation/walking is a bonus for you, Boston hands down. We like to stay in the Back Bay area, just because it seems centrally located. Duck Tours are top notch. The tour of Fenway is fun, even if you aren't a baseball fan. Even though it's a chain, I love Legal's clam chowder and have even had it shipped with dry ice.

 

[JimMIA]

Even though it's a chain, I love Legal's clam chowder and have even had it shipped with dry ice.

We don't eat at Legal Seafood in Boston, but everywhere else we've ever dined with them it's been excellent.

The best "chowdah" I've ever had was on the "Cape Cahd," at Land Ho in the little town of Orleans. Best evah!

 

[NotUrsula]

Boston is more focused on history, and Chicago is more about art and architecture -- and maybe food (not that Boston doesn't have plenty of good food, but I'm not aware of as many major summer food events as in Chicago.) Depends on which you are more in the mood for. Downtown Chicago normally has major conventions nearly every weekend that drive prices up in summer, but most of the ones I'm aware of are sticking with virtual this summer. Both cities will require you to walk and/or use public transit because parking is quite scarce.

Charleston is great, and I love the place dearly, but August isn't a time of year when it really shines, although the nearby beaches are certainly popular in summer. Best time for Charleston is spring, when the flowers are blooming EVERYWHERE. (Fall is nice too, but really expensive; there are a couple of major conventions that are there in fall that drive prices WAY up.)

 

[disneyseniors]

I have only ever been to Charleston on a girls trip. It was in June or July. We rented a huge beach house on Isle of Palms Island. It was a beautiful place on the ocean. It didnt' seem too hot to me and I'm from way up North in Mn. We were close enough to cross the bridge and visit all the sites in Charleston. There's so much to see and do there. I would recommend the carriage ride guided tour through old Charleston with it's history and wonderful houses and churches. We even went on a haunted tour - didn't see any ghosts though, LOL. We toured Middleton Mansion and the only tea plantation in the US. There is much more, and I would definitely go back there anytime.

 

[TexanMinnie]

Are you driving or flying? How do you feel about public transportation? If you are flying and public transportation/walking is a bonus for you, Boston hands down. We like to stay in the Back Bay area, just because it seems centrally located. Duck Tours are top notch. The tour of Fenway is fun, even if you aren't a baseball fan. Even though it's a chain, I love Legal's clam chowder and have even had it shipped with dry ice.

We are flying. We would definitely walk and take advantage of public transportation in any of the cities.

 

[3boymthr]

Lots and lots of history in Boston. We live locally but did a couple’s escape weekend at The Revere Hotel on Stuart street. Very nice. Our room had a balcony and views of downtown. Their room service and restaurant have very good food. There is a garage in the basement if driving but it’s also centrally located if you want to walk to the common or to Faneuil Hall.

If you are into brewery’s then the Samuel Adams Brewery is in Boston. You can do a tour. If you like Italian Pastry hit Mikes bakery in the North End. For handy take out Faneuil Hall. If you have specific types of food you are interested in check out the Phantomgourmet.com. It’s a local tv show that does reviews of restaurants across New England.

For something different you can do a tour of Fenway. You can also do a tour of Boston Harbor Islands. George’s Island has a civil war era fort you can explore.

 

[monsterkitty]

We've done all three in the warm months. Boston by far is our favorite.

When we had to change our Mexico trip for next week, Boston was our first choice but we couldn't get into the Marriott Vacation Club there.

 

[cheryl.UK]

We visited Charleston for a couple of days in august 2019. It was so hot that even at 8am it was too hot to walk around. We are used to Florida in August but this was something else.

 

[GAN]

To add.... Boston has a bunch of great outdoor beer gardens. So nice to grab a couple beers in the nice weather and watch the city go by....

https://www.boston.com/food/beer/2021/04/19/boston-beer-gardens-open-2021/