An Instagram Guide to Boston

Visiting Boston During Fall

Our trip to Boston was everything I’d hoped it to be. Charlie and I didn’t take long to feel at home in the city; it held an undeniable charm – there was a buzz that you get from big American cities, and yet a calm that you don’t get in places like London or New York. Each neighbourhood had a different vibe, and two in particular captured our hearts. It wasn’t long before we both agreed that Boston was our favourite U.S city that we’d ever visited.

Today I’m going to share a few of our favourite places – this is by no means a full guide to Boston as we were only there for a few days, but rather a continuation of my ‘Instagram Guide To…‘ series – as I like to think that I have a well tuned radar for finding those instagrammable spots in each city!

Visiting toward the end of October seemed to be the perfect time. It was still fairly warm (around 20 degrees celsius) meaning we didn’t have to pack bulky coats, and the streets were decorated tastefully with Fall/Halloween ornaments which added to the charm.

By far our favourite area was the ‘Old Town’ of Boston, based around Charles Street in the Beacon Hill area, Charlie and I certainly felt most at home around here. As well as adorable flower stalls, cupcake bakeries and coffee shops, there were plenty of picture perfect streets all in the traditional Boston red0-brick style, and porches decorated to perfection. We happened to stumble upon a tiny alley called Acorn Street, and there was honestly a queue of young couples and groups waiting to take a photograph on what they said was the most ‘Instagrammed street in Boston’ – so naturally, we had to give it a go too!

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We strolled to the end of Charles Street, taking in the beauty of the towering townhouses that made us feel so at home, and were rewarded when we discovered the ‘Sweet’ bakery – I opted for a Red Velvet cupcake while Charlie tried the more seasonal ‘Smores’ flavour – we both concluded that they were the best cupcakes we’d ever eaten! (And I’ve eaten a LOT!)

For sustenance, we grabbed coffees from Tatte – a Boston favourite which SO many of you recommended on my Instagram – and after a morning strolling through Beacon Hill we walked the very scenic route through Boston Common toward Newbury Street – a picture perfect shopping street with many of my favourite stores including Kate Spade, Kiehls, Reiss and more! Charlie was happy too as there was a Le Labo, so he spritzed himself in his favourite cologne before we googled a spot for lunch.

Below – Boston Public Library is well worth a visit, the architecture is unlike anything I’ve ever seen before!


We stopped at Buttermilk & Bourbon for lunch where we both ordered the buttermilk chicken and waffles (scrumptious!) and a seasonal cocktail, before making our way to the Prudential Centre where there were even more great shops. I stopped in Club Monaco – of course – before we headed back to our hotel for the afternoon.

The following day we went to another neighbourhood which we’d heard great things about; Cambridge is an area about 15 minutes drive from the centre of Boston, and it’s home to the world renowned Harvard University. You can stroll through the grounds yourself of have a student guide you around; but it’s well worth a visit – especially if you want to channel your inner Elle Woods like I did!

There’s another Tatte bakery across the road from Harvard – we grabbed our morning coffee and pastries here and attempted to look studious to fit in with the Harvard students inside!

That evening back in central Boston, we had a table reserved at Grotto – a family owned Italian restaurant that serves some of the tastiest pasta dishes I’ve ever experienced – I had to beg Charlie for more of his starter as it was so mouth watering, but I had the last laugh when my main course arrived – the seasonal Pumpkin Risotto that I’d heard so much about – and it didn’t disappoint!

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Head over to my YouTube channel for more of our Boston adventures, and check back in a couple of days for our spooky day in Salem!