From the morning coffee to the evening Guinness, this is what the Gary's perfect day in Boston would look like...

I visited Boston as a child but little did I know, many years later, I would move there.

I had done so much research on what to do and what to see prior to making the big move but getting lost in Boston was by far the best way to explore this captivating city.

Early morning iced coffees

My typical day would start early to catch the morning rush of Boston. It’s pretty much mandatory to start off with an iced coffee, regardless of the weather. Then head to the nearby T stop to get the blue line into the city. I would typically get off at Government Centre or Aquarium to grab a coffee nearby. Aquarium T stop is stunning during the summer months as it’s right beside the harbour which is packed with boats, yachts, and sailing boats heading off to places like Salem, the Cape, Provincetown and so many more spots. There’s also an amazing American flag swaying in the wind under the arches of The Boston Harbour Hotel which is so cool for pictures. Some nice coffee shops around would be the Tradesman Coffee Shop (their breakfast sandwiches and pastries are heartbreakingly beautiful) and wander to the steps of the harbour and meet friends to enjoy the view.

Lunchtime strolls and sweet treats

Boston is one of those cities where you can pretty much walk anywhere, usually if I was around the Seaport area I would make my way to the North End for a stroll and of course a cannoli from Bovas Bakery on 134 Salem Street. Walking through the North End is like stepping back in time in a way. The buildings are red bricked old style architecture yet the streets are alive with everyone looking for a unique Italian experience.

Some tips for lunch or dinner if you did end up staying for the whole day – head to Bricco (their Massachusetts pumpkin ravioli is amazing) or Carmelina’s which offers such a fun experience with friends that’s budget friendly. There are so many boutique shops around the area, make sure to check them out and head to Bovas for a cannoli or a pastry. It’s also convenient that the Rose Kennedy Greenway is nearby to take your sweet treats, they have swinging benches which is ideal to occupy and watch the afternoon go by.

Afternoons in Boston Common

After reenergising in the Greenway, usually I would stroll into the city. You can take the green line at Government Centre if the weather isn’t great. The stroll through Boston Common is a bucket list item in Boston, especially during the height of each season. Winter and summer months transform that area into the most beautiful space, so make sure to take a lot of pictures during the changing seasons. Head into the Thinking Cup or Tatte Bakery nearby on Boylston Street to grab a grilled cheese to take away.

Theres also an outdoor library during the summer months which is fantastic to browse some vintage covers or even some new editions that have been donated to the shop.

Pre-dinner potter around Newbury Street

Once we’ve reached the end of Boston Common, the public garden is fantastic to walk by, especially in the summer months when the pond is refilled with wildlife, but don’t get too close to the swans.

Newbury Street is the place to go on a day off – to grab a coffee or snack or to even chill alone with a book or music. They have so many shops, restaurants, cafes, and local boutique businesses which are great to wander into and learn about their trades.

Levain Bakery is a MUST – their cookies are New York famous. They also have amazing options for coffees and space outside to watch the world go by. If meeting friends, there are a few lunch spots nearby to have a drink and catch up. Solas Irish Pub is located in the famous Lenox Hotel which is located on Boylston Street and has an amazing menu of Irish inspired dishes. Their Guinness is also great. They have an outdoor terrace which is ideal during the summer.

Evenings on a sunny terrace

If the weather was on our side, we might head down to the Charles River Esplanade to watch watersports on the river and meet the neighbourhood's friendly dogs.

As the evening approaches, there are so many dinner options, including Joes, City Table, and Parish Café and Bar.

The day wouldn’t be finished without calling into an Irish pub to meet a few more friends or colleagues. For my route home on the blue T line, The Dubliner or Emmets near Centre Plaza are always a good shout to chill and catch up with people about their day. Make sure to check out their terrace in the summer months. The amount of fellow J1/Grad visa friends you can make there is great.

Watch the sun set from East Boston

After getting the T back to East Boston, it’s always nice to stop and watch the city from afar. East Boston is famous for its views of the city so make sure to head up there and check it out.

There is so much to see and do in see in Boston, no two days will ever be the same. My main advice to anyone who has days off or even evenings to fill, make sure to get up and get out into the city to explore. Those summer months go extremely fast and before you know it, the time for scarfs, hats, and gloves are upon you

If you fancy immersing yourself in a new city, check out our working holidays in the USA.