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how to spend a long weekend in boston ma

It was during a cold winter evening that I grabbed my MacBook and searched Skyscanner for the cheapest flights to the US. Fate may have it that Norwegian Air were having a sale on their flights to America, and I narrowed my choices down to New York and Boston. It might surprise you that while I may love visiting the USA, I’ve never actually been to New York! I’ve always felt more of a draw to the West Coast, and it’s definitely on my to-do list but I don’t feel a great sense of urgency to go just yet. I decided on Boston, did I know much about Boston? Not at all, but flights were around £300 each so we decided to book up a long weekend in Boston and forget about it for six months.

Those six months soon rolled around and before I knew it I was frantically googling ‘things to do in Boston’ worrying that I’d booked the trip in haste and we’d be left wandering around aimlessly for 6 days. I couldn’t have been more wrong. I absolutely adored Boston, and there was never a boring moment. Since we’ve been back, I haven’t stopped harping on to everyone how amazing Boston is how everyone needs to visit. It’s also worth mentioning that the flight took six hours which blew my mind! Much more bearable than the 10+ hour slog to Los Angeles.

Here’s how to spend a long weekend in Boston, Massachusetts!


The Lowdown

Location: Boston, Massachusetts

Length of Stay: 5 nights

Vital Info: Wear comfy shoes, we walked 55 miles in total!


Where To Stay

Not having visited the city before, I based our hotel booking on Tripadvisor reviews and getting the best rated hotel for our budget. I’d forgotten just how expense American hotels are, in the end we booked the Hyatt Regency in Downtown for around £1300 for the five nights. The hotel provided a good base for our adventures and the location was ideal. I think the hotel itself could benefit from a refresh but I find that hotels in the US are generally very similar and not usually design-led or contemporary unless you can shell out around 1K a night!


What To Do

We found that a long weekend (5 nights!) was the perfect amount of time to spend in Boston, and I could even have stayed there longer! We wanted to make the most of our time here, so we packed our days to the max and enjoyed a couple of trips outside of Boston….


Go To A Red Sox Game At Fenway Park

You can’t go to Boston without a visit to Fenway Park, the oldest baseball stadium in the USA! We booked our tickets around a month before we went, and I think we spent around $150 on the pair. I won’t lie, baseball can be a bit boring at times and there’s a lot of faffing around but it’s all part of the experience. Yes I did the typical tourist thing and bought myself a foam finger alongside the biggest coke I’ve ever seen. The buzz and atmosphere at the game is well worth the dollars, and a great way to spend a sunny evening


visiting fenway park on a weekend in boston

Spend A Morning In The Beacon Hill Area

The historic Beacon Hill neighbourhood is a truly beautiful part of Boston. Think brick row houses, cobbled paths, and a very European vibe. Most of the buildings are protected due to their historical significance and therefore the heritage is nicely preserved. If you’re looking to get THE shot for Instagram then Beacon Hill is a good choice of backdrop, and the famous Acorn Street is renowned for its Insta popularity. My top tip is get there early, as it’s a very popular area with tourists and can get quite busy. Beacon Hill also boasts a buzzing restaurant scene as well as number of cute independent boutiques.


beacon hill boston
What to do on a weekend in Boston

Visit Harvard University

But whatever you do, don’t assume you can walk there from your downtown based hotel. What were we thinking! Harvard University is situated in Cambridge and is a fair walk from the centre of Boston so I would recommend jumping in an Uber. It was quite surreal walking around the University grounds that we’ve all heard of and seen in the movies! Ok yes I am referring specifically to Legally Blonde. The major bonus of visiting Harvard was actually the nearby vegan restaurant Veggie Galaxy which was absolutely insane. But yes, back to Harvard, it was a fun way to spend a couple of hours and gaze at all the stunning architecture. Did I buy a Harvard sweatshirt? You bet I did.


how to spend a weekend in boston massachussets
things to do on a weekend in boston

Jump On A Train To Salem

This was my first time experiencing US rail, and it was certainly interesting. I felt as though I had travelled back to the 1920’s with the leather seats, wooden interior and actual human train people who shouted the next destination down each carriage. It was different, but quite cute. Although I’m sure the daily commuters will have thoughts otherwise. You can buy weekend tickets which cost $10 and allow unlimited rail travel (I’m not totally sure on the destination cut-offs but these tickets were fine for visiting Salem) so it was a real bargain. We hopped on a train to Salem and arrived within 30 minutes. I had a brief knowledge surrounding the Salem Witch Trials but it was fascinating wandering around and understanding more about the events and Salem’s spooky history. Charlie and I fell in love with this little town, and it was a real highlight of the trip. During our day trip we visited the The Witch House, The House of the Seven Gables and the Salem Witch Museum. I’m going to put together a separate post on how to spend a day in Salem, so stay tuned!


how to spend a weeend in boston massachussets2
visiting boston and going to Salem
visiting salem from boston


Spend Your Dollars Down Newbury Street

We didn’t head to Boston to shop, but I’d be lying if I said it wasn’t on my mind to check out what the shopping scene was like. My favourite area for shopping was Newbury Street, a charming area in Boston’s Back Bay which is home to a number of boutiques, restaurants, galleries and salons. We found a great little bookshop called Trident which is also home to a restaurant which boasted a number of great vegan options, so naturally we went a few times! The start of Newbury Street is where you’ll find the high-end boutiques such as Chanel, but wander down further and you’ll be greeted with the likes of Reformation, Brandy Melville, Vans, Zara, Forever21 and so on.


newbury street boston shops
newbury street boston

Enjoy A Picnic On Boston Common

When we went it wasn’t exactly picnic weather in Boston but if you’re visiting during the summer, a picnic on Boston Common would be just lovely. It’s one of the oldest public parks in the America and is extremely well maintained with a no-smoking rule in place too. You can hire a boat out on the lake, or simply sit and watch the world go by. It’s also right on the edge of Beacon Hill (and the Cheers bar!) so it’s a beautiful area to spend a day exploring in Boston.


boston common swan boat
boston common what to do on a weekend in boston

Catch A Bus To Cape Cod

I had no idea Cape Cod was so close to Boston, but we stumbled across this gem of a fact when researching for our trip and boy am I pleased we did! We headed down to the Cape via a bus at the South Station which was so easy to pick up. I say bus, it was more of a school-trip style coach but very comfortable for the hour or so drive. We picked an excellent day to go to the Cape as the sun was shining and we didn’t need our jackets for the first time all weekend. There’s tonnes of areas you can explore within Cape Cod but we chose to get off at Hyannis which was apparently John F Kennedy’s favourite place to holiday. Think white sandy beaches, crystal clear blue waters, traditional sweet shops, and a whole load of seafood. Being vegan, I didn’t sample any of the fishy foods but I did find a vegan cafe which blew my mind. We arrived in Hyannis at around 11am and left at about 6pm which gave us ample time to wander around and stop off for drinks.


spending a day in cape cod from boston
visiting hyannis cape cod from boston

Treat Yourself To A Pint In The Cheers Bar

This was more ‘Charlie’s to-do list’ than mine but it was still good fun. I’ve actually never watched Cheers but who doesn’t know the theme tune! There’s actually two Cheers bars, one a the Front Hill Market and one on Beacon Hill. I preferred the Beacon Hill branch personally and it was a nice stop for a quick drink after a long day of walking. In terms of the menu, there was nothing for vegans and it was generally just burgers/pastas that sort of thing.


Cheers bar boston beacon hill


We had a pretty intense 5 full days in the city and we certainly made the most of our time in Boston. Had we stayed a couple nights longer, I might have been tempted to hop on a bus to New York! Not only is there plenty to do in the city, there’s tonnes of adventure within just an hour’s journey. For our next East Coast trip I would definitely be tempted to fly in to Boston (shortest flight!!), spend a couple of nights before moving on to New York and Washington. What  road trip that would be! Have you ever considered a long weekend trip to Boston?


Don’t forget to check out my post featuring the best Instagram spots in Boston Massachusetts.

Check out all my USA travel posts here.


  • June 6, 2019

    I love Boston sooooo much I’m dying to go back – it’s been about 10 years since I was there! Loved this post x

  • June 6, 2019

    Omg it’s all so pretty! I always wish we travelled more! Maybe we will do one day.
    Caitylis x x

  • June 7, 2019

    Such gorgeous photos! I’d honestly love to do a road trip around the USA because it’s just so pretty there, so much to see & do!

  • Jess

    June 9, 2019

    Boston is one of my favourite cities ever. I love Beacon Hill and would happily move there if I could!

    The Crown Wings | UK Travel & Lifestyle Blog

  • June 9, 2019

    Such gorgeous photos from your trip! It looks amazing and with all your travel tips I feel like I could easily book a trip! Xx

    Lauren |

  • June 10, 2019

    £300 is so good for flights! I need to go one day x

  • June 11, 2019

    I’ve never been abroad but I love this. It’s so handy to read f you’re going away to Boston. I know many people that really love the place. I’ve been wantin to visit the US since I was a kid. Sounds like you had a good time and there’s lots to do x

    Lauren | By Lauren May

  • Maiya

    June 14, 2019

    I’m loving these travel posts, so much info! xx

  • Amy

    July 21, 2019

    This looks like such a fun and amazing trip. I have never been to America and in truth, it hasn’t really appealed to me either, however these pictures may have just swayed me.

  • Emma

    May 8, 2020

    Very helpful info as I have never been to boston but am planning a trip to new york/boston in May, what time of year did you go? Probably the weather will be similar in May.
    Greetings from Berlin

  • Jay

    July 1, 2020

    Lovely, but you didn’t do the Freedom Trail?? This is an absolute must-do, otherwise one hasn’t truly ‘done’ Boston.

  • January 30, 2021

    Fabulous pics! That’s such a lovely place for a staycation!


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