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The Only Boston Travel Guide You Need To Read

Boston is a city that is enriched in history, sports culture, and is home to many Colleges and Universities. Boston has a mix of unique colonial-style buildings and Georgian architecture which gives the city a charm of its own. It is mostly known for the well-liked TV Show “Cheers”, a show that was based in a Boston Bar.  The popular sitcom shows us different types of loveable Boston characters. 

 Elizabeth Keenan.

Thinking of taking a trip to Boston or even moving there for a year or two? Looking for some travel tips on what to see and do in this popular City? Need a Boston Travel guide? We interviewed Irish Blogger Elizabeth Keenan who lived in Boston for two years. She tells us what it’s like to rent there, how cold it gets in the Winter, and where are the best places to go in the Fall/Autumn. 


Here is your essential Boston Travel Guide:


Hey Elizabeth! Thanks for chatting with us today. 


First things first, what made you decide to move to Boston?

I moved to Boston after college with my old job. The company operated in Ireland & America and wanted to move my position to the Boston office. My mother is actually from Rhode Island, which is beside Massachusetts, so it was a great opportunity for me to be close to family as well as try to live in a new city. 

Boston Skyline. Picture by Elizabeth.

It’s nice that you could be close to your family. Is Boston expensive to rent? Where would you suggest the best places to look online for accommodation?

The simple answer, yes. Boston prices are similar to NYC and it is the third most expensive city to live in the US. Typically for a 1-bedroom apartment, you’re looking at the very least $1700+ a month. It doesn’t really get cheaper as you go outside the city unless you go quite far out. 


You’ll also need the first month’s rent, last month’s rent, deposit, and sometimes a realtor fee of 1 month’s rent, so the equivalent of 4 months’ rent upfront! Then you’ll need to get furniture etc. so it can be quite an expensive city to move to. 


Zillow is obviously a popular place to look, and we found our apartment there but there can also be suspicious listings so make sure you do your research! Trulia.com can also be good, I’d suggest looking at some Facebook groups too! Some nice areas to live-in would-be Allston, Brighton (a little further out) & Brookline. Out in Cambridge is of course lovely too and a very young & hip area! 


That’s good to know. If someone was looking for a Holiday/short stay, where are the best places to stay in Boston?


If you’re visiting on a shorter holiday time frame I’d suggest staying as close to downtown as you can. Back Bay is a great area if you want to be central. If you’re on a budget but want to be in the city, I’d suggest Allston or Brighton. The Verb Hotel (Fenway area) is a cool spot to stay in! 

Verb Hotel. Picture by Elizabeth.

 They all sound great. In your opinion, where are the best places to see in Boston?


There’s a lot to do in Boston! Personally, the #1 thing I’d suggest doing is the Freedom Trail. It’s a free trial and laid out in the brickwork of the streets. It starts at Boston Common and goes for 2.5 miles and has 16 sites along the way, including Faneuil Hall, USS Constitution, and Bunker Hill Monument (great views). 

Prudential. Photo by Elizabeth.


Other things to do in Boston:


•Visit the Skywalk Observatory at the top of the Prudential, this is basically Boston's empire state building! Go see a game at Fenway Park - Baseball is much better in person! 

•Explore the Harborwalk - so long and so many great spots to look at the skyline of Boston!

•Go see the Boston Irish Famine Memorial! It’s a mini-park with two sets of statues of people suffering during the famine and a family that made it to America. 

•Explore the North End (old Boston)

•Visit the Museum of Science - You will not regret it! 

•Walk & shop on Newbury street


All of these attractions sound amazing! What are some cheap things to do in Boston? Are there many free things to do in Boston?

Well, the Freedom trail is free to do, however, some of the sites have fees. There are loads of free things to do in Boston! 

  • Walk around Boston Public gardens & Boston Common. 

  • Check out the Boston Public Library

  • Explore Beacon Hill and go to Acorn Street

  • Visit Harvard & Explore Cambridge 

  • Go to Boston Public Market

Acorn Street. Photo by Elizabeth.

It’s great to know you can travel on a budget.  I suppose we couldn’t do a Boston travel guide without asking where are some unique places to eat in Boston?

There are so many places to eat I don’t know where to start. Boston has such a variety of food. Obviously, it’s a MUST to go eat at Faneuil Hall, you can experience the hustle and bustle and try the different food stalls - all of which are great!


For lunch spots Tattee is my favourite, there are a few around Boston! For dinner Maggiano's Little Italy is lovely. Regina’s Pizzeria is a must, and you cannot go to Boston without a trip to Mikes for a cannoli!


These places sound delicious to eat in. Where are the best coffee places in Boston? 


I’m going to say Tattee again! Now there are coffee shops on every corner in Boston and you’ve got every chain coffee shop you can think of! Tattee is such a good brunch, lunch, or coffee spot! George Howel and the Thinking Cup are great ones for downtown. 

I have a blog post on this where I’ve put in the best coffee shops by the area (https://everythingobsessed.com/best-coffee-shops-boston-area/)

Sounds like a great blog post. Thanks for sharing. What are some fun things to do in Boston at night?

Charles River. Photo from Elizabeth.


I’m not a big nightlife person but there is most certainly nightlife in Boston! Now keep in mind that most everything is shut by 12/1 am. Fenway is a great area to stay if you like a bit of nightlife! 


Noted. What are some cool things to do in Boston in the Summer?

Boston has a lot of cool things to do in the summer. It gets really hot and has a great buzz! 

  • Walk along the Charles River. 

  • Go to the 4th of July concert (usually free)

  • Get a cruise around the harbour

  • Go on a whale watch

Fall/Autumn seems to be a popular time of year in Boston. Can you tell our readers of some Fall activities in Boston they can do? 

All of the New England areas of America are absolutely breathtaking in Autumn! You’ll never see so many colours of leaves in your life! 

  • Visit a pumpkin farm & try all the pumpkin flavoured everything! 

  • Ghost and Gravestones Tour

  • Take a day trip to Salam if you like Halloween!

  • Best time of year to stroll down the Charles River - Make sure to bring your camera!

    Sounds like an exciting time of year. What are some fun things to do in Boston in Winter?

Winter is a great but very cold time in Boston. You definitely need to know that in the colder months it can get down to -25 celsius, which is crazy cold - believe me! 

Boston in Winter. Photo by Elizabeth.

But Boston goes all out for Christmas and has trees and lights up everywhere! Some fun things to do in winter are:

Snow in Boston. Photo by Elizabeth.

  • Ice skating in Boston common

  • Visit Snowport (Christmas markets) 

  • See the lights at Christopher Columbus Park

  • Visit SoWa Open Market

Oh, that sounds freezing! But it’s good to know you can still have fun in the Winter. Finally, what advice would you give to someone hoping to move to Boston?


Save some money before you go! It’s a great city to live in and makes the rest of America more accessible! Join Facebook groups and get involved in some activities to get to know people. People in Boston are much friendlier than a lot of other cities and it’s an easy place to make friends! I’d also say be prepared for FREEZING winters because it gets so cold and you’ll need proper snow boots, a jacket, etc.! 


That is brilliant advice. Thank you, Elizabeth. 

For more great travel tips from Elizabeth check out her Blog:

www.everythingobsessed.com

Instagram page: @elizabethkeenanx

Youtube channel: https://www.youtube.com/c/ElizabethKeenan/videos

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