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First settled by English Puritans in 1630, Boston is one of the most historically significant cities in the United States. The Massachusetts state capital was the starting place of the American Revolution and therefore played a pivotal role in the establishment of an independent America, meaning there is plenty to fill a 2 day Boston itinerary.
But Boston’s significance didn’t stop there. Since the American Revolution, it’s seen more than its fair share of firsts. Boston can claim to have produced the U.S.’s first public park, first public school and first subway system. Add to this a fantastic shopping scene, exceptional food and being surrounded by a stunning coastline, it’s no wonder that Boston welcomes over 22 million tourists every year.
Dozens of direct flights from Europe make Boston one of the most accessible American cities for European travelers. And generally, Boston is an excellent place for first time visitors to the States.
Getting to Boston
By air
Most travelers to Boston arrive by air, and Boston’s Logan International Airport is just 2.5 miles from the historic city center. Subway trains, buses and ferries operate between Logan and Downtown Boston, along with the option of using taxis or the usual ride share apps.
Boston sees daily direct flights from several European destinations as well as those further afield in Asia and the Middle East. As a hub for Delta and JetBlue and service from all the major U.S. carriers, getting to Boston is easy from almost anywhere in North America. Find the best option to suit your plans by comparing flights before you book.
By train
If you’re getting to Boston from elsewhere on the East Coast, rail is a great option for reaching Boston. Amtrak’s Acela Express and Northeast Regional provide dozens of daily services between Washington D.C. and Boston via New York.
The average journey time from Washington DC is seven to eight hours and from New York is around four hours. Acela trains are quicker but can be considerably more expensive. The earlier you book, the cheaper the tickets.
By bus
Boston is served by a number of intercity bus lines, with several daily services from New York as well as services running north along the New England coast. Greyhound, Flixbus, Megabus and many independent carriers operate these services, so compare options when you book.
Where to stay in Boston
There are so many fun and interesting neighborhoods to choose from; it’s almost impossible to pick a favorite. For our 2 day Boston itinerary, a central location means you can spend more time sightseeing and less time commuting.
Downtown Boston
Boston’s historic heart, Downtown is great if you’re looking for somewhere close to all the sights. Being such a walkable city, staying downtown is ideal if you want to maximize your sightseeing time and get around on foot. Our top picks here are the elegant and upscale Godfrey Hotel Boston and historic The Dagny.
Back Bay
Boston’s affluent West End, Back Bay is another top pick if you’re looking for somewhere central. On the doorstep of Boston Common and Copley Square, Back Bay is the perfect spot to stay to start the Freedom Trail.
The Charlesmark Boutique Hotel is just steps from Boston Public Park, the oldest in the United States. For somewhere a little more budget friendly without compromising on location, check out The Revolution Hotel.
2 Day Boston Itinerary
Day 1: The Freedom Trail
Visiting Boston without walking the Freedom Trail would be like going to New York and skipping Times Square. Starting from Boston Common, this 2.5 mile trail takes in 16 historical sites leading to Bunker Hill Monument. The Freedom Trail is the gem in the crown of our 2 day Boston itinerary.
Highlights include Boston Latin School, the Old State House and the Paul Revere House. The penultimate stop, the USS Constitution, is well worth some extra time. There’s an excellent museum telling the story of the oldest warship still afloat anywhere in the world, and, as a bonus, you can step onboard this piece of maritime history.
You can follow the trail at your own pace, or for the ultimate experience, join a tour. Discover the story of the American Revolution with a three-and-a-half hour small group walking tour and get the lowdown on all 16 sites from a knowledgeable local guide. If you prefer doing your own thing, but don’t want to miss out on any of the history, you can download a self-guided tour and map to help you along the way.
Whichever you choose, make sure to check out our guide to the Freedom Trail in one day.
Special Mention: Quincy Market
Boston’s foodie hotspot, Quincy Market is conveniently situated around halfway along the Freedom Trail. Quincy Market is part of the historic Faneuil Hall Market Place and has been around for almost 200 years. Nowadays, it’s home to 18 restaurants and 35 food stalls.
For a true taste of Boston, head to Union Oyster House. A local institution established in 1826, they do everything from oysters and clam chowder to the classic beans on toast which earned Boston its moniker “Beantown.”
Boston Chowda Co is another must for seafood lovers. They’re famous for their New England Clam Chowder, but the pot pies and lobster rolls are just as sumptuous.
Day 2
Whilst the Freedom Trail covers all the essential Boston historic sights, there’s plenty more to see and do on our 2 day Boston itinerary. Spend your second day in Boston exploring some of the city’s lesser-known gems.
9 am: Breakfast in Back Bay
If there’s one things Bostonians take seriously, it’s their coffee. After all, it’s the birthplace of Dunkin’ Donuts. You should probably stop by one of their many locations during your time in the city, but for breakfast head to Trident Booksellers & Café.
A quirky Indie hangout, Trident is a favorite among Boston’s student population. They’re known for their insane selection of tea, and their all-day breakfast menu is the perfect way to set yourself up for the day. Choose from hearty sandwiches, freshly griddled toast and waffles, eggs and freshly baked pastries.
10 am: Take in the view
From Trident, take the short walk to Copley Square. This historic plaza is home to some of Boston’s finest architecture. Check out the Old South Church, completed in 1873 and the renaissance-style Public Library.
At the south side of Copley Square, View Boston is the place to go for the best view of Boston. From the top floor of the Prudential Tower, you can take in all the sights of the city and admire the Freedom Trail sites you saw yesterday from a different angle. Book tickets in advance to skip the queue and save on entry fees.
11 am: Boston Tea Party Ships & Museum
The Boston trolleys are the iconic orange and green trolleys that have been touring the streets of Boston for decades. Tickets are valid for a full day and you can get on and off as many times as you like.
Travel tip: A fun way to reach the Tea Party Ships & Museum is to hop on a Boston Trolley Tour.
The Boston Tea Party was a protest against the Tea Act, introduced by the ruling British colonist in 1773. The Act allowed the British East India Company to sell Chinese tea in the colonies tax free which angered the Sons of Liberty (a group of native Americans who opposed British rule). Their protests, which ended with the destruction of 342 chests of tea, were seen as a great success in the journey to independence.
Get your tickets for the museum before you go to save time.
1 pm: Lunch at Legal Seafoods
We usually prefer to recommend local, independent restaurants, but sometimes the local chains are too good to miss. Legal Seafoods is a Boston icon. Born in Boston in 1950, they’ve grown from a market fish stall in Cambridge to a household name with 25 locations across five states.
Their Harborside location is a 10-minute walk from the Tea Party Museum. Many a Bostonian would agree with me in saying that a trip to Boston (at least for first-timers) should include a meal at Legal Seafoods.
2:30 pm: New England Aquarium
When beside the seaside, an aquarium is always a good idea. With seals, sea lions, penguins, octopuses and sea dragons, plus thousands of species of fish, this not-for-profit aquarium is one of Boston’s top attractions.
You could easily spend the best part of a day here, but you can get around the more unique exhibits in a couple of hours, making this an ideal fit on our 2 day Boston itinerary. Buy tickets in advance to get the best value.
5 pm: Harvard
Harvard University is the oldest university in the United States having been founded in 1636. An acclaimed Ivy League college, Harvard is one of the world’s most prestigious schools. Wander around the grounds of this U.S. icon or, to learn more, take a guided walking tour of the campus.
Next, head along to Harvard Square. The place where Harvard students go to shop and relax, this is one of Boston’s most hip and trendy areas. If bookstores aren’t your thing, use your time here to take a tour with a tasty twist. Chocolate Tours run every weekend giving you the chance to sample artisan chocolate, ice cream and even chocolate tea, all whilst learning more about the university.
7 pm: Dinner in Harvard Square
Harvard Square is Boston’s latest foodie destination and you’ll be truly spoiled for choice. For something quirky, Alden & Harlow is a subterranean restaurant serving a local take on Mediterranean classics.
If you prefer to stick to the traditional flavors of the USA, check out Mr Bartley’s Burger Cottage. Ever since 1960, this Harvard icon has been dishing up classic American burgers to everyone from Harvard students to Johnny Cash and Bob Dylan.
9 pm: Relax with a nightcap
Round off your 2 day Boston itinerary with a tipple at Shays Pub & Wine Bar, Harvard Square’s most loved bar. With a massive wine list and a selection of beers from across the world, this unpretentious spot is the perfect place to get a feel for Harvard life. If the weather’s on your side, you’ll find it hard to leave the lively beer garden. No rush though, they’re open until 1 am on the weekend.
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