My Favourite City,  Travel

My favourite city: Boston, MA – The Long Tall Ally

Last month I launched a brand new series on this here blog – My Favourite City. All the bloggers and writers I adore will be telling me all about their favourite city: why they love it, special memories from their time there, and all the secrets they’re willing to spill. This month I spoke to my wonderful friend, spectacular storyteller and Global Travel Analyst, Ally.


TCL: Hey Ally, thank you so much for being a part of this new series! Let’s get straight to it – what’s your favourite city?
Ally: Boston zoomed straight into the top spot when I spent a week there in October as part of a longer road trip around New England. I’d wanted to visit since I was about 13 and so was worried it wasn’t going to live up to the hype, but it actually surpassed it. I can’t wait to go back.

Boston skyline | this city life

It’s been on my wish list for some time too! What do you love the most about Boston?
It had a great mix of culture, shopping and restaurants and bars, and the city is really packed with attractions for every type of tourist. It’s a walking city and the architectural mix of historical New England and modern skyscrapers is nothing short of breathtaking. Even if you just have time to wander through the city, you’ll see some amazing sights.

So, I know you’re all about the adventure! Tell us all what you got up to there
Boston was my first stop on a three week solo road trip around New England, and on the first night I met up with a good friend’s cousin Vanessa. We agreed to meet at the Harpoon Brewery Octoberfest and so after dumping my stuff at my hostel I hopped in an Uber to the Seaport District. Having been warned by Vanessa that the queue was insane, my Uber driver dropped me at the back of a line that stretched off considerably into the distance and screeched off into the sunset.

It was only when Vanessa called and asked where the heck I was that we realised, I was in the queue for a Bernie Sanders rally at the Massachusetts Convention Center! Unfortunately I ditched Bernie and we ditched the Octoberfest in favour of going to Papagayo (283 Summer St) and getting smashed on Rona Rita’s (a Corona upended in a Margarita – yum) Sorry Bernie!

(Ed note: Haha…this could only happen to you Ally!)

What’s your favourite thing to do in Boston?
I couldn’t pick one favourite thing to do as I did so much in the time I was there, but on a nice day you can’t beat a wander through Beacon Hill, particularly the little boutiques on Charles Street. Special shout outs to Second Time Around (82 Charles St) – a cool discount store with lots of designer goods, Black Ink (101 Charles St) which is a ‘one-stop design shop’, and The Flat of the Hill (60 Charles St) where I could have spent all of my money on tchotchke and gifts.

Boston red sox | this city life

I don’t know anything about Bostonian dishes, but what was your favourite thing to eat and drink there?
It’s a Boston cliché but you have to go into the North End and go to Mike’s Pastry (300 Hanover St) for one (or more) of their famous cannolis. There’s also a branch up in Harvard Square (11 Dunster St) which is quieter. They’re insanely good, like my mouth is salivating just thinking about them now…

For drinks, taking the T to Davis Square (one of the top ten hippest places in America) and joining the nearby Tufts students in bar hopping is a great idea. Saloon (255 Elm St) is a subterranean speakeasy with leather chairs, dark wood panelling and a cosy intimate feel that plays up the prohibition vibe. The bartenders were ace at mixing us round after round of bespoke cocktails and the atmosphere was lively but laid back.

Did you find out an interesting fact about this city?
The Boston University Bridge on Commonwealth Avenue is the only place in the world where a plane can fly over a car that is going over a train that has a boat sailing underneath!

What top 3 things would you recommend to do in Boston?
1. The Mapparium at the Mary Baker Eddy Library – a three-storey glass globe built in 1935 that you walk right through the middle of. It’s a very surreal experience because the acoustics mess with your head and you can hear yourself in surround sound at deafening volume. There’s an old fashioned grocery store next door which has a hidden high end sneaker store behind the Snapple vending machine. Sneaky!

2. Whale Watching from the New England Aquarium – a four hour boat trip out to Stellwagen Bank National Marine Sanctuary. I was really lucky as the day I went we saw ten minke whales up close, three of whom decided to frolic directly under our boat! It was a beautifully sunny day but also freezing when motoring at high speed out to the bank so wrap up warm.

Boston whale watching | this city life

3. Improv Asylum – a theatre group who do improv and sketch comedy shows. It’s like being at a filming of ‘Whose Line Is It Anyway’ and it is absolutely hilarious. I had tears streaming down my face with laughter and didn’t even mind being there on my own, or getting hauled up on stage to use my life to riff off!

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What’s the first city you remember visiting?
London with my family. We stayed in Lancaster Gate at a Merchant Navy hotel thanks to my Dad’s job and did all the touristy things. It was round about this time of year and I was about six. I remember kicking leaves in Hyde Park and going to the Tower of London. I also remember how loud the city was, there didn’t seem to be any escaping it!

What do city breaks mean to you?
It’s about the chance to put real life on hold for a while and explore another way of living. You might only have a day or you might have a week but being in the heart of a new city is exciting and revitalising.

What advice would you give people wanting to go on a city break?
Plan ahead. I always worry that I border on being too organised, but actually taking time to study the guide books before departure means that I can work out itineraries and see the things I want to without having to traipse all over the place in a haphazard order. Splitting the city up into zones meant I could spend time soaking up the atmosphere in each neighbourhood without having to dash about like a blue-arsed fly!

Boston architecture | this city life

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Balcony or beach? Balcony – not a fan on sand in delicate places!
Luxury or budget? Both because they offer different experiences
Culture or adventure? Culture definitely
Local lingo or mother tongue? Give the local lingo. Gotta be in it to win it
Metro or walk? Walk, you get to see more
Sunshine or snow? Sunshine – snow is good but not when it goes slushy

Thank you my lovely friend Ally for sharing your favourite things about Boston, Massachusetts. You can see more of her brilliant stories over on Twitter @thelongtallally – give her a follow!

Want to take part and tell me all about your favourite city? Pop me an email at and I’ll whizz back the questions.

Charley is a professional copywriter and tea-lover currently living in Leeds. She writes about city living and city travel (with a few cats thrown in).