6 Days in Boston: The Thanksgiving Itinerary

It feels amazing when you finally visit a dream destination that’s been on your bucket list forever.

If you’re wanting to add America to your travel list, it’s great to start with the East Coast. Not only is it the closest to the UK (we’re talking shorter airplane time), but it offers some of the finest that the country has to offer. One of these, and the one we chose, is the city of Boston, in Massachusetts.

One of my biggest ideas of the country is from watching Winter films in small towns or big cities, and people wrapping up warm and snuggly to bustle around. So heading to Boston in the Winter was a dream. If you enjoy seasonal holidays where you can fully embrace it, this city can get freezing cold!

We mainly chose Boston because we were making it a family-visiting holiday. Which also meant we were lucky enough to see more of what it’s like to be a Boston-local, and explore the housing areas of the city. It also meant we were able to visit the local town of Salem, so keep an eye out for a Salem post soon.

Day 1

I was slightly anxious about my first ever long-haul flight – long-haul to me being 8-hours. But our timings were pretty much perfect. Leaving the UK early in the morning meant that we arrived with a few hours left of the day still. For the first day we arrived at our family’s home, and got settled into our accommodation for the week. After we’d settled, we headed into Boston to get our bearings, and have a mini-look around to see what our plans would be for the week.

Within walking distance we found Quincy Market, a food hall, and the first sight of Boston’s famous Clam Chowder. Having a nice dinner booked for later we stuck with a simple slice of pizza each, and carried on with our exploring.

BRICCO
Italian restaurant Bricco is located in North End, one of the oldest residential areas in Boston, famous for its Italian cuisine and pastry shops. Bricco fits perfectly with its self-proclaimed ’boutique Italian food’, and it’s a real treat. We wished we’d saved it for another night, because we were so tired from our travels we were almost falling asleep at the table. Helped along by the dim lighting and relaxed atmosphere. But nonetheless it was a lovely venue to kick start our trip.

I went for the 7-Spiced Murray’s Brick Chicken, a signature of the venue. On the side I tried a VuVu Cosmopolitan, one of the drinks from their cocktail menu. There’s lots to choose, both drinks and food. And it all sounds delicious.

After almost falling asleep in the restaurant we headed home for a good night’s sleep, and ready to start the next day.

Day 2

The next day was Thanksgiving in America, so a very different look on our other holiday days. Being in a home, rather than a hotel, it meant we were treated to the full experience. We watched the Macy’s parade on the tv, and cooked a full roast turkey dinner. For something I’d heard so much about, I was absolutely buzzing to experience it for myself.

After lunch, we headed out for a walk, and an excuse to see more of the local areas of Arlington. We saw wild turkeys wandering around the houses. Cute and exciting for us Brits, but apparently they were ruining everyone’s flower beds. On our way along the walk we said good morning and happy Thanksgiving to all the locals we saw.

Similar to Christmas in the UK, there was nothing much more to do other than take the day to relax. So after this we didn’t do much with our day 2. We cosied up in the living room and watched the American Football (and learned about ‘Turducken’. Honestly, look it up!).

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Day 3

We started day 3 with a trip to the local supermarket, and left with brown paper bags. We mainly bought snacks – and chocolate so that we could see what the difference was. No comment there, it was mixed reviews from our party. The rest of the day was kept a little simple. As there was a football match on (England versus USA no less) we focused our day around our evening again. Grabbing a quick dinner and booking in for a last minute activity.

We signed up for a Ghost Tour around the city at night, with one of the many local tour guides. When on a tour you bump into tens of other tours, seeing how popular they are. Make sure you find one and book on so you don’t miss out. With this ghost tour we explored cemeteries, government buildings, gardens and hotels. If it’s history you’re interested in, these tours are great, and you can really find out how much history there is in Boston.

After our tour we found a bar, and decided to relax with a couple of drinks. When visiting somewhere like the USA, for me it’s the little things you experience. On this evening, it was sitting at a bar, on a bar stool, with my jacket hung up on one of the hooks underneath. Watching the many American Football teams on the many tvs.

Also, remember, wherever you go and however old you look, chances are you will need to show your ID. Always make sure you don’t leave the house without it.

Day 4

After exploring the city by night, we explored by day. On day 3 we booked again onto another tour. This time onto the Boston Duck Tour, something not to be missed. Again, super popular, so booking ahead is a must. The tours are led by tour guides in costume on the amphibious vehicles. All the guides have an incredible knowledge of the city, so you learn a lot while on board. You explore the land, first following the route of the Boston Marathon, and throwing in a trip on the river.

After our tour we were dropped off by a shopping mall, and an opportunity for me to try another tick off my bucket list – The Cheesecake Factory. I ordered a Key Lime Pie flavoured slice of cheesecake, but be warned of the big portion sizes when ordering. I left feeling sugar-filled and a bit sick having eaten the entire thing with whipped cream on the size.

After a (very slow!) walk to walk off the cheesecake-sicklies, we walked along the harbour and to a treat we’d booked for ourselves for another dinner evening. We’d booked into Smith & Wollensky, an amazing steakhouse by the harbour.

SMITH & WOLLENSKY
While quite expensive, if you’re looking for a treat dinner this is a great choice. With the right seat you’ll have great views of the Boston Harbour, but even without it’s a stunning venue to spend your evening in. While we were there, sat in our booth, it was full of couples with the same idea, and evening of getting dressed up and having a posh dinner.

I went for their signature, the Coffee and Cocoa Rubbed 10oz Steak, and for something I’d never usually try, it was delicious. Already served with what they called ‘Angry Onions’, we ordered french fries as a side, and an extra side of sprouts for me – something you’ll see on a lot of menus. Carrying on my trip with the theme of cocktails, I had a Spicy Cucumber Margarita, and boy was it spicy.

Day 5 & 6

On day 4 we did the biggest thing on my list. Having just finished frantically watching Hocus Pocus before October was over, when we arrived in Boston in November my biggest wish was to visit the nearby Salem. See my separate Salem post coming soon.

On day 5 we were due to go home – my temporary American dream was over. Again, we’d done a pretty good job with our travel planning, giving ourselves one last day of exploring the city, then heading home in the evening so that we could sleep the whole journey home, and wake up when we arrived at our front door around 7am.

We dropped off our bags for a small fee for the day at a local hotel, and had one last walk around the city. One of the last delights we’d heard about and had to try before we left was the Cannoli – in particular, a cannoli from Mike’s Pastry.

Mike’s Pastry
Located in the North End area of Boston, Mike’s Pastry is a must when visiting Boston. Open since 1946, they’ve been serving their versions of the cannoli to Bostonian’s and tourists. With the wrong timing you could be queuing around the corner to get your hands on one, but it’ll be worth the wait. The cannoli is a traditional Sicilian pastry that’s crispy on the outside, and creamy on the inside.

I went for a simple but tasty chocolate dipped cannoli, covering with icing sugar, then we went a found a seat down by the harbour to enjoy. Word of warning – make sure you take cash with you, as they don’t accept card in store.

And that was my brief, but enjoyable, introduction to America, and hopefully the first of many. If you haven’t yet visited any part of the country, but, like I was, am longing too, then New England is a great part to start with. It’s got interesting history to learn about, lots of restaurants and bars to go to, and heaps of American culture.

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