Travel Diary: A Guide to Boston, Massachusetts

Back in May, as a bit of a birthday trip, we headed to Boston for a much-needed reunion with our American friends, but also to check out the historic, bustling capital city of Massachusetts. Here's a little look at what we got up to...

For those of you unfamiliar with the city, Boston, Massachusetts is famous and historical for a whole number of reasons. Boston was one of the first British settlements, alongside Salem, and was founded in 1630 by Puritans. During the American Revolution, Boston was home to several key events which went on to shape American laws and their way of life, including the Boston Massacre (1770), and the Boston Tea Party (1773). Since the American independence from Great Britain, Boston continues to play an important role for America as a centre for education and culture.  

Besides being steeped in American history (although as a British person, nothing feels in the slightest bit old), Boston is also renowned for being a beautiful and thriving city. Most famously, it's recognised for the Samuel Adams Brewery, delicious seafood (particularly oysters, lobster rolls and claw chowder), as well as being the home of famous Boston Red Sox. Three things you will see in some capacity quite literally everywhere you go. We also came across so many awesome independent record and comic book stores, bars and shops which provided plenty of souvenirs to come home with.

Walking around Boston, it felt small compared to other American capitals and you can easily see all of the major sights over a few days. That said, there is more than plenty to occupy your time. Here's some of top spots I'd recommend checking out whilst you're visiting Boston, Massachusetts:

1. Fenway Park and Stadium, Home of the Red Sox 


You can't go to Boston and not stop by Fenway Park. Whether you decide to venture inside the stadium itself or just take a stroll around the outside, it's a sight to behold. Since 1912, Fenway has been the ballpark of Major League Baseball's (MLB) Boston Red Sox and hosted eleven World Series, in which the Red Sox have won six. It's also been used to host countless stadium concerts for the likes of Billy Joel, BeyoncĂ© and Lady Gaga. It has also been used as a filming location of many, many films over the years; including Good Will HuntingThe TownTed and Ted 2, Moneyball and The Perfect Catch to name, but a few. 

If like me, sports aren't really your thing, I think you can still completely appreciate the stadium as an impressive landmark of the city. We decided to take a guided tour during our visit there and our guide could not have been more knowledgeable and entertaining. It was genuinely very interesting and gives you the chance to sit on the deck atop of Fenway's famed left-field wall, the Green Monster - a highly sort after seat. 

A tour of Fenway Park lasts around 45 minutes, priced at $25 per adult and $12.50 per child at the gate.  

Outside of the stadium itself, Fenway Park has a whole host of bars, restaurants and music venues to enjoy too, including House of Blues and the MGM Music Hall. Even if you don't wish to attend for anything sports related, it's well worth visiting during the evening time to catch a show, browse the shops or grab drink/a bite to eat.

Honourable mention - Loretta's Last Call, Fenway Park

One of the biggest highlights for me, besides the stadium itself was stumbling across Loretta's Last Call. As regular readers of my blog will know, I'm a huge lover of country music and all things Americana - and Loretta's Last Call celebrates just that. 

Loretta's is Boston’s original country venue, offering an authentic menu of southern cuisine and country music tunes. They also host weekly line dancing and live music nights, as well as a weekend Bluegrass Brunch. It's a fantastic place to grab a cocktail or an ice cold beer before a game, or just enjoy an all-American meal. I would highly recommend stopping in and sampling the brisket and cornbread if you find yourself in Fenway anytime soon. 

2. Union Street and Downtown Boston City Center 


Downtown Boston is considered the city centre, and has been the main hub for Boston since the 1700s. The strange thing about Union Street and the Boston City Center to me was how much it looked like and felt like home. It's clear in the architecture that it was founded by Brits and that influence still feels very present today. If you're British and have explored a lot of America, you may find it a little off-putting - but it's still great to explore and there are tons of little shops and tours you can take advantage of. 

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Very popular tours which take place all around the centre include the many boat trip excursions, accompanied by the Freedom Trial guided walking tours, Boston Ghost Tours and the Boston Crime Tour (which explores Boston's mobsters - ideal for true crime lovers). Alternatively, you can just enjoy wandering by yourselves, which is easy to do!

3. The Freedom Trail 



If you're keen to get your steps in whilst visiting Boston, The Freedom Trail is an excellent opportunity to explore all the major tourist spots and Boston history. The Freedom Trail is a 2.5-mile-long path through Boston that passes by 16 locations significant to the history of the United States. 

It winds from Boston Common in Downtown Boston, to the Old North Church in the North End and the Bunker Hill Monument in Charlestown. Although, if you are walking around Boston, you're likely to see majority of the locations without even meaning to follow the trail markers on the floor of the streets.   


During the trail you'll find mostly a collection of museums, churches, meeting houses, burying grounds, parks, the Boston Tea Party ship, and historic markers which shaped the American Revolution and American history as a whole. 

Many tourists choose to take this route with a tour guide for the most insight, but you can easily do it alone. You'll see plenty of costumed tour guides on-route, dressed in their colonial attire!  

4. Quincy Market 

If you're looking for some of the best grub in Boston, Quincy Market is an iconic, must-see foodie spot. Located right in the heart of Boston Market Square, Quincy Market is a multi-level food hall with over 50 eateries, vendors and kiosks. There is absolutely something for everyone no matter what your dietary requirements. 


As well as all of the typical Boston favourites such as oysters, lobster rolls and chowder, you'll also find all-American sandwiches, comfort eats, veggie and vegan dishes, sushi and ramen bars, extravagant sweet treats and much more. Quincy Market can get pretty packed around lunchtime so plan your visit accordingly, but I would absolutely recommend eating here during your trip to Boston.

5. James Hook & Co. Lobster 


Speaking of food - one of the priority locations on my list was absolutely James Hook & Co.. For the best lobster in Boston, this is your essential first call. A family business founded in 1925, James Hook is today managed by four siblings of the third generation of the Hook Family. Known around the country for quality wholesale lobster and seafood products, they also offer casual dining to their lunch crowd, located on the historic Boston waterfront. 

James Hook is particularly popular due to their epic portion sizes. The lobster roll is a New England staple and James Hook pack each and every roll with the biggest, meaty lobster tossed in mayo or butter for that authentic taste.  

If a lobster roll isn't your preferred order, however, you probably haven't had a good one yet. If you insist on something else, they also serve up an incredible lobster mac & cheese, shrimp cocktail (huge king prawns) and a selection of warm chowders. All of which are to die for - and easily the best seafood I've ever eaten. You can also purchase seafood to take away or packaged frozen including scallops, baked haddock, lobster pie and mussels. 

Naturally, due to its fame and almost landmark status, James Hook will get very busy around lunch time daily and you can wait up to an hour in line. You cannot book or reserve a table, but be sure to get their in plenty of time Don't be put off by the queues, it's worth the wait. 

6. The New England Aquarium 

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The New England Aquarium is a non-profit organisation and conservation project located in the heart of Boston, Massachusetts. They exhibit so many beautiful species, including harbour and northern fur seals, California sea lions, African and southern rockhopper penguins, giant Pacific octopuses, sea turtles, and thousands of saltwater and freshwater fish.

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So I didn't know it at the time, but I was recovering from what I later found out was pneumonia during our trip to Boston. After a long day of exploring the city on foot, it was time to visit the aquarium and I was struggling. I thought it best to sit it out, but our friends said to give it a go - and I'm so incredibly glad they did because the aquarium was genuinely so impressive. We stopped for a quick rest in the aquarium cafĂ© before entering inside and I was, thankfully, quickly distracted from my illness when given the opportunity to touch the string-rays. 

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Aquariums I've visited in the UK have always been pretty lacklustre, but this was really something. Besides having so many different interesting and unusual species and creatures, the building itself was beautifully designed. The majority of it wrapping around a giant ocean tank and all of the enclosers are very spacious and well maintained. I can see why so many people choose to get married there.

7. Acorn Street and Beacon Hill 


One for you Instagrammers, if you happen to be nearby Beacon Hill, you might want to stop by Acorn Street. Just a short walk away from the Freedom Trial, it is considered to be one of the prettiest streets in all of Boston, and definitely the most photographed street. 

Acorn Street represents colonial Boston. It was on this quiet, charming street that 19th century artisans and trades people lived. Today the row houses are considered to be a prestigious address in Beacon Hill - but people do indeed live in them so do be respectful of residents. A few streets away, you'll find some quaint cafes and upmarket boutiques and shops.

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Well, that's it for another adventure. I hope you find this guide useful, when planning your own visit to Boston, Massachusetts or should you find yourself there in the future. We had an absolutely amazing time exploring with our American friends and am so grateful to them for spending the week with us.

Until next time fellow travellers, 


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