The best Boston, Massachusetts travel guide: explore historic landmarks, vibrant neighborhoods, and hidden gems with this comprehensive post for an unforgettable visit to Beantown.

Visiting the historic and vibrant city of Boston soon?

Where the cobblestone streets of its iconic neighborhoods echo with the footsteps of revolutionaries, scholars, and sports fans alike.

Boston offers a captivating blend of old-world charm and modern sophistication just waiting for you to explore ;).

While I had visited Boston a few times before 2022, when my son and his girlfriend moved to Boston for graduate school that year, I took this opportunity to visit as often as I could in the two years they have lived there (so far anyway!) to get to know this magnificent city at a more detailed level.

And now I have plenty of travel knowledge to share with you ;).

Be sure to read the Top Things to See and Do in Boston as well – you can find that post here.

In a rush?

The Little Details

How to Get to Boston

Whether you prefer flying, driving, or taking the train, Boston is easily accessible from all directions.

Logan International Airport serves as the city’s main airport, offering numerous domestic and international flights daily. And is less than a 15 minute taxi or Uber ride into the city center.

If you’re driving, major highways like I-90 and I-93 provide easy access to the city.

And for those opting for public transportation, Amtrak trains connect Boston with neighboring cities and states, providing a convenient and efficient way to travel to this vibrant metropolis.

How to Get Around Boston

Boston’s compact size and pedestrian-friendly streets make walking a convenient and enjoyable option, allowing you to soak in the city’s rich history and charming architecture at your own pace.

Additionally, rideshare services like Uber and Lyft are readily available for quick and convenient transportation around the city.

The public transportation system (the ‘T’ in local lingo) is incredibly efficient, budget friendly, and quite extensive providing easy access to all major attractions and neighborhoods.

One thing to be advised upon, is that you will pay a HEFTY price to have a rental car in the city. Parking is a rare commodity and most hotels charge upwards of $60/night for their lots.

If you are planning a day trip out of the city, my suggestion is to rent a car just for that one day and not your entire trip.

Best Time of Year to Visit Boston

Having visited Boston in spring, summer, and fall, I truly feel there is never a bad time to visit Bean Town. While I have not experienced a winter visit yet, the last few years seem to have been pretty mild winters in the Northeast which would allow for some great sightseeing with minimal crowds ;).

How Many Days You Need in Boston

While a 2 day getaway can provide a taste of Boston’s iconic landmarks such as the Freedom Trail, Faneuil Hall Marketplace, and Fenway Park, ideally, spending three to four days in the city allows for a more extensive experience.

A longer visit would allow you to delve deeper into the city’s rich history with time to visit some of its renowned museums, savor the culinary scene in the North End, and even take a day trip to a nearby town such as Salem, Nantucket, or Newport, Rhode Island.

Best Places to Stay in Boston

I have listed below all the hotels I have stayed at in Boston in the last couple of years while visiting my son – and honestly, you cannot go wrong with a stay at any of them!

The Whitney Hotel

This is one of my favorite hotels in Boston!

And it is located right in the heart of my favorite Boston neighborhood of posh Beacon Hill.

The Newbury Boston

Discover the epitome of sophistication and luxury at The Newbury Boston hotel, where timeless elegance meets modern amenities.

Located directly across from the beautiful Public Garden and on the iconic Back Bay shopping street of Newbury Street, this 5 star splurge will make you wish you stayed longer no matter how long your visit is ;).

Four Seasons Hotel Boston

Also centrally located across from Boston Common and the Public Garden, Four Seasons Hotel Boston provides elegant accommodations with exceptional service – oh and each floor has a candy vault – which is never a bad amenity!

The Liberty, A Luxury Collection Hotel

Part of the Marriott Hotel chain, this is a perfectly located and quite hip place to stay – especially if you are using or collecting Marriott points!

The lobby is an energetic place to hang out in this historic old jailhouse building – even if you don’t end up staying here.

We stayed here in mid November 2022 and they already had their unique Christmas decor out of multiple trees hanging from the ceiling ;0.

The rooms are a bit darker than the other hotels on this list and a standard room is rather small – however as always – the location in Beacon Hill and right next door to Mass General Hospital – (don’t worry – you never hear the noise from this massive hospital system) is quite enviable.

There is also a T station right across the street to make getting around Boston super easy…

Hotel Commonwealth

If you are in town for a Boston Red Sox game or to visit someone attending Boston University, then Hotel Commonwealth is your closest higher end property option.

Some of the rooms have a fantastic view of Fenway Park even (just a head up though – the I-90 freeway is in between the hotel and the ballpark – but with very well soundproofed windows ;0).

Best Places to Eat in Boston

Buttermilk and Bourbon

A Southern restaurant in a Northeast city? Yup.

Although truth be told – I was sold with the ambience the second I walked in anyway. Oh and the cocktails were 😮👍🏻.

Mamma Maria

With cobblestone views of North Square (the oldest public square in America) and impeccably decorated dining rooms (the restaurant entails multiple smaller rooms) as well as being located directly across the street from the Paul Revere house on the Freedom Trail – this North End (Boston’s version of Little Italy) restaurant is so far my favorite in this old neighborhood ;)).

Don’t forget to make a reservation though!

Time Out Market

Because I am such a picky eater and my husband is the complete opposite, we have found that food halls and markets work really well for us when we travel.

This way my husband can try something creative or just nothing my fussy palate would tolerate and I can have something non-creative ;0. This is usually something with potatoes or pasta or steak for me 😂.

Time Out Market Boston is a hip vibrant culinary food hall with stalls from some of the best chefs in Boston. And one of my favorite places to eat in the city!

Grill 23 & Bar

An excellent choice if looking for a high end steak and potatoes restaurant with an energetic vibe in an aesthetically pleasing restaurant ;).

Reservations are a must here though!

Davio’s Northern Italian Steakhouse

While I know Davio’s is a mini-chain (11 locations in the US), it is another great steakhouse option. We ate at the Back Bay location however we walked by the Seaport location once and I was impressed with the views of the Boston skyline that location has.

You really can’t go wrong with either option in Boston proper. And if you miss this in the city – looks like there is a Davio’s at Logan Airport even ;0.

Warren Tavern

Warren Tavern in Boston, steeped in history and charm, offers a quintessential New England experience with its cozy atmosphere, traditional pub fare, and a fascinating past dating back to the Revolutionary War era.

The French onion soup, burgers, and shepherds pie at this historic pub were insane 😮.

Make a reservation in advance if you can – this tavern is a must stop in Boston ;).

Legal Seafoods

Legal Seafoods in Boston is a beloved institution, offering fresh and delicious seafood dishes that capture the essence of New England’s culinary heritage in every bite.

While you can most certainly get better lobster if you drive up to Maine, Legal Seafoods is an iconic Boston restaurant that is somewhat of a mainstay on most what to do in Boston lists…

There are many locations to choose from in Boston proper. We decided to eat at the Seaport location and enjoyed the pleasant views (even with the rainy weather).

Contessa

With an enviable location on the rooftop of the upscale Newbury Boston Hotel, brunch at Contessa is a delight.

Reservations are available online 30 days in advance and I highly recommend putting a reminder on your phone to get a coveted spot here!

Mike’s Pastry

If you are a lover of Italian cannolis – don’t miss Mike’s Pastry, a beloved Boston institution serving up this and other sweet delights that will satisfy any sweet tooth.

While there is almost always a line for this bakery, it is quite efficient and goes pretty fast. Although, I cannot speak for what it would be like if the line wraps around the block (our line just went to the back of the bakery and was about a 10-15 minute wait).

The Bell in Hand Tavern

Experience the historic charm and lively atmosphere at the Bell in Hand Tavern, the country’s oldest tavern, where you can sip on local brews and soak in the rich heritage of this iconic establishment.

While I don’t know if I would have much more than a beer/cocktail and a snack (or burger) at this pub, it is one of the most popular pub stops in the city.

Photos courtesy of Bell in Hand Instagram

Modern Pastry Shop or Bovas Bakery

Many Bostonians argue that the cannolis at Modern Pastry Shop are actually better than the more famous Mike’s Pastry cannolis. While I have not actually tried the cannoli’s from Modern – I figured it was worth mentioning to you in case you want to do a taste test yourself…

And even more in the know – say Bovas Bakery beats them all!

They are all located relatively close to each other – all in the North End neighborhood…

Top Things to See & Do in Boston

There are so many things to see and do in Boston, the list is deserving (and somewhat necessary due to length of post!) of its own post.

Therefore – here is a quick list of the top things to do in Boston.

But for a more detailed list and many more suggestions, be sure to read my ‘Top Things to See and Do in Boston” guide. You can find that article here.

• Photograph Acorn Street (the most photographed street in Boston)
• Walk the Freedom Trail
• Tour Fenway Baseball Park (and catch a Red Sox game if they are in town)
• Relax in Public Garden
• Shop on Newbury Street
• Walk along Boston Harbor
• Visit the JFK Library
• Explore at the Harvard Museum of Natural History
• Wander the famous and sacred grounds of Mount Auburn Cemetery
• Do a Duck Tour
• Feel your IQ rise while wandering the grounds of any of the higher institutions in the city – including Harvard, MIT, Boston College, or Boston University
• Tour the Boston Tea Party Ship
• Walk the Charles River Esplanade
• Take a day trip to Salem, Nantucket, Cape Cod, or Newport, Rhode Island

What to Wear in Boston

Clearly the answer to this question lies solely in what season you are visiting.

Fall can have a nip in the air to it but if you are walking a lot – layers would be crucial for those moments when you heat up.

Summer and spring visits would be perfect with sundresses and a light jacket or sweater.

And then of course – a typical winter would require a snow jacket and appropriate winter accessories…

However here are a few of my own travel staples:

I hope you found this Boston Massachusetts travel guide helpful in planning your Beantown adventures!

Whether you’re exploring iconic landmarks along the Freedom Trail, taking in a Red Sox game at Fenway Park, or indulging in fresh seafood at Quincy Market, Boston’s rich tapestry of experiences promises something for every traveler to cherish and remember.

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Life is short, the world is wide.

I want to make some memories.

~Mamma Mia

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Have a wonderful day my friend! I hope something makes you smile today ;).