Are you planning a trip to Boston? There is so much to see and do in this city from historical landmarks like the Freedom Trail to delectable culinary delights in the North End. Whether you’re a first-time visitor or a seasoned traveller, these 12 experiences for your Boston itinerary will make your time in Boston unforgettable.

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1.) Bag a Banging Breakfast

The Friendly Toast – If you want to splash out then head to Back Bay for The Friendly Toast. This trendy brunch spot serves a huge menu of fun, delicious and hearty breakfasts. Alongside you can order free refill coffee (hot and iced) or alcoholic treats galore. The doughnut breakfast sandwich is an exceedingly naughty treat and the burrito is filling and spicy.

Dunkin Donuts – For a cheap and authentic breakfast bite, you have to visit Dunkin! Dunkin Donuts was created just around the bay from Boston and has been producing reliably delicious doughnuts ever since. Dunkie’s is a Boston staple, with a huge number of residents popping in for their daily coffee. Wherever you are staying, there should be one nearby as they have 85 locations in the city. As well as the doughnuts, they have breakfast sandwiches so if you don’t have a sweet tooth, you’ll be fine.

2.) Visit Boston Common

The heart of Boston for centuries, this is Boston’s favourite park. Make your way to the Frog Pond first, in winter there is an ice rink here. (Check our blog post all about Skating at Boston’s Frog Pond HERE). In summer it is a splash pool (great for kids but maybe a little weird to walk around Boston soggy).

See if you can spot the huge grey squirrels that call the common home (and if you are picnicking, make sure you keep an eye on your snacks because they love those human foods).

Probably the most famous thing to do is to take a swan boat out on the lake. The boats have been owned and family run since 1877 and they are utterly charming. These are not little pedalos for individual use but big pedalled boats with six benches and swans on the end. They glide around the water, giving you the chance to relax and enjoy the sunshine.

3.) Walk The Freedom Trail

This is kind of a 10 in one as the Freedom Trail is a walking path,easing past the cities most iconic locations. Most, but not all are related to the War of Independence, and it is an absolute must for all visitors to the city. Here are our favourite stops along the way:

• Massachusetts State House – On a sunny day, you cannot miss the gleaming dome of the Massachusetts State House. In fact, in all weathers it glows gold with gilding over a wooden frame. The building stands proud on Beacon Hill, overlooking Boston Common, befitting its role as the seat of government for Boston since 1798.
• Granary Burial Ground – With 2300 markers, this used to be the main cemetery in Boston’s nd holds the graves of many important city residents. Look closely at the gravestones and you will see some of the more common motifs of the time. A skull and crossbones (in rather a cartoony style) adorns several stones.
• Omni Parker Hotel – This is not officially a part of the Freedom Trail but it is along the way and worth a quick stop. The hotel lobby itself drips with vintage charm so pop in but then head down to the shop/starbucks on the side. Here you can grab a slice of Boston Cream Pie, made by the place it was created and sold at a much better rate than in the hotel’s dining rooms. You can also grab a drink at The Last Hurrah. This is the bar where Charles Dickens first performed A Christmas Carol to a rapt American audience and when JFK proposed to Jackie O.

• Old State House – Just in front of the building is a round cobblestone marker on the floor. This marks the spot that the 1770 Boston Massacre took place, a skirmish between angry Bostonians and British army. Breaking up a brawl, the soldiers resorted to firing their guns and killed five civilians
• USS Constitution – She was built way back in 1797 and is still a commissioned warship, making her the oldest still afloat. The grand dame looks pretty good for her age, especially considering the bettering she took and withstood beautifully from the British HMS Guerriere. She performed so well, in fact, that she earned the reputation “Old Ironsides”.

• Old North Church – Every school child in America will be familiar with the phrase “One if by land, two if by sea.” This comes from a poem all about Paul Revere’s midnight ride, when he travelled from Charlestown carrying the message of the British army’s movements. The church’s sexton Robert Newman gave the signal with two lanterns so Revere could spread the alert which allowed the Patriots to prepare for battles in Lexington and Concord. Plus, this is Boston’s oldest church, standing here since 1723 so pop inside if you can. The pretty white wooden pews and balcony, along with the brass chandeliers are very photogenic.
• Bunker Hill Monument – A grand granite obelisk, standing at 63m high atop Bunker Hill celebrates one of the first major battles fought between the British Redcoats and the Patriots. Of course the battle wasn’t actually on Bunker Hill but nearby Breed’s Hill but let’s not split hairs. You can climb the monument to truly finish the trail (if you have any energy left after climbing Bunker Hill itself).

4.) Savour Some Seafood at Union Oyster House

This is the oldest continuously serving restaurant in the entire USA. The Union Oyster House has been dishing up delicious Native oysters and creamy chowder since 1827 but it is so much more than an eating spot. Union Oyster House is in a building with hundreds of years of history. It was home to rebel printers, adventurous French royalty and John Hancock’s office (yes, the signature guy). Come for the food, and you will really enjoy it, and stay to look around the whole place. There’s loads of info and memorabilia about Boston, the building, restaurant and even the absolutely lovely owner and his family.

Here’s what we ate on our visit:

• Their home-cooked cornbread is served to all diners, free of charge.
• A classic clam chowder, practised and perfected over generations. It was seafood-y, creamy and sweet with clams.
• A cold seafood sampler with plump raw oysters and clams, plus three perfect prawns.
• One medium, steamed lobster to share. It was served with butter but didn’t need it. It was so moist and delicious. Peeling seafood is my happy place and we made swift work of it!

5.) Take a Drink in Boston’s Oldest Taverns…kind of

Drinking in a pub with some history behind it just hits different. It is nice to sip a pint and imagine all those who have gone before, especially when they include some of Boston’s most famous revolutionaries. The good news is that three of Boston’s oldest drinking holes are right opposite each other on Marshall Street (…again, kind of).

• Green Dragon Bar, 1654 – The oldest pub in Boston doesn’t actually stand where it began but its boozy lineage is still impressive. The original tavern was torn down in 1832 but the name lives on at the new “Green Dragon Bar”. Inside, it feels like a classic Irish pub. There is a small stage in the corner with live music at the weekends. The original location was a meeting places for Freemasons and both the Sons of the Revolution and their British Redcoat counterparts. In fact, Paul Revere, whilst enjoying a bevvie here, overheard the news that he then disseminated to his Patriot buddies during his midnight ride, so it has rather an important place in history.
• Bell in Hand Tavern, 1795 – New kid in town if you compare it to Green Dragon Bar, the Bell in Hand was established by Boston’s town crier Jimmy Wilson. He only served ale, it was presented in two glasses, one for the drink and one full of froth. I guess it was great for the people that like it, “just so”? The bar had a few locations but settled here in 1844 and you can see the original bar from the 1700s which came along with them. These days it has the feels a bit like a nice Wetherspoons (for my British readers) or a bit of a fancy college bar (for those of you from the USA).
• Warren Tavern, 1780 – Warren Tavern has been in its current Charlestown location for almost 250 years, making it officially the oldest pub in Massachusetts. It replaced another pub, burned down by the British, possibly during the battle of Bunker Hill. The new tavern was named for a Major General called Doctor Joseph Warren who was killed during the battle. This was another watering hole popular with the big names, Paul Revere, George Washington and Benjamin Franklin. Those boys really liked a swift half. The tavern’s interior has a country pub feeling with lots of wooden beams but a menu full of Boston restaurant favourites (chowder, rangoon and burgers)
• The Union Bar, 1826 – Part of Union Oyster House, this large wraparound bar is full of locals who come for a delicious beer and a few seafood bites. The smaller bar down the stairs has been here since 1826, before the restaurant took its current form. Washing a nice pint down with half a dozen oysters is about the coolest way to start a bar crawl that I can think of.

6.) Isabella Stewart Museum

Don’t you just love it when a museum is as beautiful as the art itself? Well, the Venetian-style vill of Isabella Stewart Gardner is a perfect example. Isabella Stewart Gardner was a collector of all things beautiful. From medieval religious carvings to stunning Japanese screens and Renaissance portraits, there is a bit of everything.

She was so proud of her collection and the way it was displayed. So proud, in fact that in her will, she stipulated the museum be kept exactly how she designed it. This is why, after the famous art heist of 1990, the empty spaces left by the stolen art remained unfilled. Pick up one of the detailed audioguides and spend a happy hour or two working your way through the history of art and the offices at the back which give an incite to the woman herself.

7.) See the Skyline Cheaply

There are a few ways to see the skyline that don’t include an expensive harbour tour.

Take a trip to East Boston for some beautiful wooden-clad buildings, a great cider spot (more on that later) and a walk through Piers Park. The views across the water to the centre of Boston are glorious.

Even better, take the MBTA ferry from the airport to downtown. This isn’t free but a cost-effective and super exciting way to reach the city. You won’t get a commentary about the city along the way but you could always play your favourite songs and live your main character moment as you cross the bay.

8.) Eat Your Way Through the North End

You can make your own way through the area, and we have a few recommendations for you, or join a food tour like this gem we took with Secret Food Tours.

• Pizza – The undisputed champion of pizza in Boston is Regina’s. They have a few locations but it has to be the North End restaurant for us. You can sit in and pick from a wide selections of toppings. Alternatively, if you choose to takeaway a slice you get two choices, plain cheese or pepperoni. The base is thin with enough droop making it satisfying but enough structure and the crusts are chewy and moreish. Top that with a perfect tomato sauce and delightfully stringy mozzarella and you have a slice worth queueing for.

• Cannoli – An Italian pastry case stuffed with sweetened ricotta, cannoli is a naughty, quite heavy treat. There are two main spots that battle for the title of best cannoli, Mike’s Pastry and Modern Pastry. They are within a two minute walk of each other in the North End. With good eyesight you can see both! Thus, we implore you to order one from each and find your favourite.
• Coffee – Italian’s take their coffee seriously. No big takeaway cups full of cream and sugar here. A proper espresso is taken black, and quickly at a standing counter. Well, Polcari’s coffee does make a mean espresso and other coffees beside. Where they really excel though is their coffee blends which come in a huge range including special Christmas blends, fruity, sweet and very grown up combos. Buy a bag to take home for an excellent souvenir.
• Mamma Maria – No, this isn’t a dish you haven’t heard of, but just the best fancy Italian restaurant in the North End. It is perfect for date night or a special occasion, or to just take your time over excellent Italian fare. It costs a pretty penny but you won’t find heaps of pre-prepared spaghetti in cheap tomato sauce. Instead, delicate handmade pasta, perfectly cooked meats and seafood and the finest of everything is on offer.

9.) Jump on a Duck Tour

Duck Tours provides bus tours with a twist. Their vehicles are amphibious meaning they can tour the roads and the waters of a city. Yes, this might be cheesy but honestly, the thrill of your tour bus descending into the water is always exciting. Plus, Boston does it Duck Tours so well! The conDUCKtors are a funny bunch with a constant stream of facts and plenty of banter. Tours traverse the streets past some of those iconic Freedom Trail stops, the city’s wharfs and newer attractions like the Greenway and the Hatch Shell. Then, for a unique perspective they take to the Charles River. It is the coolest way to take in the city. (Oh, and they stop at a duckling statue and isn’t that the cutest thing!)

10.) Sip on a Hard Cider

Cider, or hard cider in the USA, is a big deal in Massachusettes. It could be the abundance of delicious apples, or its closer ties to the UK in its early years, but hard cider is more popular here than in much of the country. There are two places to give it a try (other than a few bars and restaurants):

Red Apple Farm

Located within Boston Public Market, Red Apple Farm sells all kinds of apple products. The donuts looked so good but we were always full (a reason to true me thinks). The cider, though is the reason you should stop by. They have three varieties and it’s only right to order the flight to try all three. However, if you are on a budget and ask nicely, they will let you try them before you choose one to buy. The red apple flavour is distinctive and delicious, and dont panic when you see the word, ”Dry”, it is definitely a medium cider.

Downeast Cider

Over in East Boston, near to Piers Park is Downeast Cider. This factory-cum-tasting experience is an exceedingly pleasant way to spend an hour. Downeast produce all kinds of unusual flavours that range from fruity concoctions to maple donut and even cider produced like a white beer (the driest option if you are that way inclined). Cider is served in flights of four small ciders and you can mix and match the flavours.

There are usually between 10-12 so with three people, you can try all of them, with one or two there are some harder decisions to be made. Flights are limited to one per person, per day and everyone is handed a chip on entry to ensure the rules are being followed. Mind you, if someone is driving, there is no harm in ordering two flights and letting the passenger princess go to town on them! It is great fun tasting them all deciding on a favourite.

(Oh, and if need to soak some of the cider up, there is a cool Aussie pie place called Seabiscuit next door).

11.) Take a Stroll Around Copley

Copley Square in Back Bay is well worth a trip. There are some beautiful buildings all set around Copley Square so it is an easy spot to walk around. The area was swampy land until reclamation and major construction in 1859 – 1900.

• Boston Public Library – Founded in 1848, and open to the public in 1854 this library was the first large free municipal library in the USA. It has been housed in the McKim building since 1895. It is a celebration of learning and McKim, the architect, wanted it to be a “Palace for the people”. The grand marble staircase leads up to the first floor past large lions atop plaques holding the names of civil war infantry units. Then you will come across gorgeous murals painted by French artist Pierre Puvis de Chavannes. From here, turn right and you will walk through to a wooden-clad room reminiscent of Venetian palaces. From here, turn left into Bates Hall, the iconic main reading room with its beautiful emerald reading lamps. You can grab a coffee and relax in the Italian-style courtyard garden, head up to the art galleries on the 2nd and 3rd floors or make your way through to the 1970s addition where you’ll find the everyday library goings-on.

• Trinity Church – The first of two churches on the square, Trinity Church was founded in 1733 but the current building was erected in 1872 by architect H.H.Richardson. He developed his own style known as Richardsonian Romanesque, incorporating European revival styles from the 11th and 12th centuries. It gives the church a distinct style that is full of stunning artworks and beautiful windows.
• Old South Church – On the opposite corner of the square is Old South Church, built in 1872, home to a congregation established in the 1600s The outside is Venetian Gothic and rather pretty, but it’s inside that the church comes alive. At the back is a series of boards which tell the story of the church and its vital place in Boston’s history. Its previous location was a recruiting location for the Union army and the inclusive nature of the church was a core principal after the civil war. It has maintained a strong dedication to diversity within its congregation and charitable efforts ever since.

• Fairmont Copley Plaza Boston – This has to be the prettiest hotel lobby in Boston. You’re free to have a little wander through its palatial corridor and elegant lobby, particularly lovely at Christmas time. When you are by the check in desks, look around and see if you can find Cori Copley, the black Labrador Retriever who is the official Canine Ambassador for the hotel. She likes a good bit of fuss.

12.) Try Boston’s Famous Dishes at the Food Markets

Boston knows good food and even better, they want to share it! There are two excellent food markets to get your chops around.

• Quincy Market – Located behind Faneuil Hall (due for a renaming soon) is a great place to grab a quick lunch, especially if you are walking the Freedom Trail. It is definitely a tourist trap but there are a few gems. Here you will find outlets of some of Boston’s most famous eateries. Pizzeria Regina has a stall here, Boston Chowda Co. serves cups of genuinely delicious creamy, clam chowder. The Dog House serves proper Fenway Franks without the need to sit through a game.
• Boston Public Market – Less touristy is Boston Public Market. Everything here is vetted for quality and is very local. There’s a great seafood shop at the back; Red’s Best is an excellent place to try a lobster roll. Also, keep an eye out for Q’s Nuts. They have a huge selection of flavoured nuts that are unusual and delicious. This is also a great place to pick up some craft beer, with loads of four-packs on offer. Finally, look out for The Popover Lady. Popovers (known in the UK as Yorkshire Puddings) is batter that puffs up when cooked in hot oil in the oven. The Popover lady tops them with sweet or savoury goodies and serves them hot to happy customers.

Where we Stayed in Boston

Trendy and affordable, The Revolution Hotel is just the sort of boutique accommodation we adore. They have a blend of large, fancy rooms and suites, small and affordable rooms (some with ensuites and some with bathrooms down the hall) and even four-bed family rooms. Our ensuite room was quite small at 130-145 Square Feet but there was room for hand luggage backpacks under the raised bed platform. Plus, when you are on a city break, why pay for loads of space when you’ll be out all day. Some of our favourite things about The Revolution Hotel:

• Free luggage storage – We stored our bags as we went sightseeing.
• A coffee shop in the main lobby – Great coffee and a relaxed vibe.
• The artwork throughout the hotel – It was so cool! Lots of the art is inspired by the history of the city, its inventions and people.
• They have a fire in the lobby – Heaven in December.
• Free WiFi – A godsend for those of us that don’t have roaming.
• Bikes – We didn’t take advantage of this as it was cold but in spring/summer, this would be ideal.

Final Thoughts for your Boston Itinerary

I love a city with layers of history and culture. I love a self-assured city that knows who it is. Boston is both of these things and makes a wicked city break! Boston is a wonderful city with so much history. It’s a big place with loads to see. Lots of it is very walkable and there’s a great public transport system so it is ideal for short-term visitors. We will be back for sure, hopefully, when the weather is a little warmer and we can picnic on the Common and stroll the emerald walk. Stay tuned, for 12 more things for your Boston itinerary to come!

Rosie xx