Most Memorable Things To Do ONLY in Boston

Boston Faneuil Hall Marketplace at night

Here’s our recommendations for the top attractions and things to do that you will see ONLY in Boston – they should not be missed!

The very first thing you’ll need to do when visiting Boston is Paahk Your Caah, because you’ll have no use for it while touring this amazing city.  Boston is a walking city with one fascinating neighborhood giving way to the next, so pack your sneakers and get out and explore. 

Many of the most interesting attractions are actually free to enter.  Just before my son left for college, we took a day and walked the city from Fenway Park, along tree-lined Commonwealth Ave, down fashionable Newbury St, through the Public Gardens, across Boston Common, over Beacon Hill down to Faneuil Hall, over to the waterfront and ended the day in the North End for dinner.  Yes we were exhausted, but we were also totally invigorated by the beauty, history and uniqueness of this wonderful city.

Boston Skyline

For First Timers
As one of America’s founding cities, there are so many historical sites spanning the entire city that you should really do an orientation tour with one of the sightseeing companies.  My favorites are Boston Duck Tours and Old Town Trolley Tours.  Both treat history with a good dash of humor and give a terrific overview of the city and its neighborhoods.  The major difference being that the Duck Tours include an amphibious journey along the Charles River with wonderful views of both downtown and Cambridge, while Old Town Trolley Tours lets you hop on and hop off to tour attractions along the way.

Old State House Boston

Boston’s most famous walk is, of course, The Freedom Trail, which is free to all.   The Freedom Trail winds its way along a 2.5 mile red brick path while revealing events and historic buildings of pre-revolutionary Boston.  You’ll feel like you are living a chapter from your America history school books.  Be sure to take advantage of the free costumed guides who lead the way.

There are many walking tours to take advantage of as well.  Some of the most popular are Boston By Foot (and little feet), Haunted Boston Ghost Tours, Bites of Boston Food Tours, and Boston City Wine Tours.

Bosston Gardens Swan Boats

Boston Public Garden –
No trip to Boston would be complete without visiting the Boston Public Gardens, the oldest public botanical park in America.  We’ve all seen images of the cheerful Swan Boats gliding under graceful bridges and you’ll definitely want to take photos of your own and perhaps a ride.  Walking through the gardens at any time of year will brighten your mood and it’s conveniently located between the Back Bay and Downtown so it makes a delightful transition.


All Roads Lead to Faneuil Hall Marketplace – No matter where you begin to tour, you will more than likely end up at the festive Faneuil Hall area which has served as a meeting spot since 1742 and always tops the list of most visited places in the USA.  Take in the street performers, souvenir kiosks, miles of food markets and restaurants, and just soak in the energy.  The marketplace at night is a sight you will long remember with twinkle lights illuminating the entire area.

Boston Faneuil Hall Marketplace at night

Ye Olde Union Oyster House – While Boston overflows with wonderful restaurants both trendy and traditional, the Union Oyster House should be experienced by all as it is the Oldest Restaurant in America and is still serving up delicious New England cuisine.  You’ll find the Union Oyster House just behind Faneuil Hall Marketplace on Union Street, where the staff has been shucking oysters at the oval oyster bar for nearly 200 years.  The building dates back to 1742 and dining here is like being invited to sit down and relax in a building that would otherwise be a museum of fine living in the past.

For another historical dining spot, stop into The Parker House, home of famous Parker House Rolls and the Boston Cream Pie!

So Many Museums – So Little Time – It’s no surprise that a city so steeped in history and learning would have many wonderful museums.  If rain dampens your visit, head straight to the Museum of Fine Arts where you can easily spend an entire day visiting with the Masters.  Check for special exhibits and promotions like the Museum Open House on Memorial Day.

Gardner Museum Boston

For a museum that is as delightful in the sunshine as it is on a cloudy day, visit the Isabella Stewart Gardner Museum.  Ms. Gardner, a notable art collector and philanthropist, designed the museum to replicate a 15th century Venetian palazzo with a stunning central court garden.  The central rooms remain just as she left them with the exception of the missing paintings stolen in a brazen art theft in 1990.  This museum is a perfect size to fit into your itinerary without being exhausting or taking up a significant part of the day.

A good reason to venture over to Harvard Square in Cambridge is to visit the Harvard Museum of Natural History.  The main attraction for me is the marvelous collection of 4,000 intricate glass blown flowers – like no other in the world.

For an emotional interlude for Boomers – a visit to the JFK Library will surely tug at your heartstrings.  The movie tribute to JFK is a tear jerker to be sure.

Boston Harbor Waterfront

Boston’s Waterfront is a delight.  Cross over from Faneuil Hall and walk the waterfront.  You’ll find famous seafood restaurants, chic hotels, the Harbor Walk, and harbor cruises.  Everyone should get out on the water to experience Boston from a fresh and dazzling viewpoint.  My favorite is the Boston Harbor Cruises 45 minute USS Constitution Cruise.  You depart from Long Wharf and journey over to Charlestown where you can  visit the legendary USS Constitution (Old Iron Sides).  They also offer a full range of cruises from Sunset, Whale Watching, Charles River and out island excursions and longer trips to Provincetown and Salem.  Or keeping with the history theme, cruise Boston Harbor aboard a wooden schooner with the Liberty Fleet of Tall Ships and feel like you’re sailing into a colonial port.

Newbury Street Boston

A Little Shopping Never Hurt!  Without a doubt there are two divine shopping streets in Boston proper.  First on my list is Newbury Street that stretches from Mass Ave to Arlington St in the Back Bay.  Lined with stately brownstones, shade trees and wrought iron fencing, it’s an elegant street for fashionable boutiques, chic restaurants and indulgent spas.  A visit to Charles Street in the Beacon Hill area will have you snapping photos of scenic side streets as you stroll along.  With fewer tourists than Newbury St, Charles Street offers great little shops and restaurants.  Our good friend Jack is the proprietor of The Sevens (77 Charles St) where the whole neighborhood goes for a pint or two – just like that OTHER bar that has become a cliche.

A bit further down Charles Street awaits a truly unique Boston experience.  The infamous Charles Street Jail was converted a few years ago into the deluxe Liberty Hotel.  Here’s your chance to go to jail and enjoy the experience.  Dine in The Clink, a restaurant fashioned from former prisoner cells – quite an experience!

Or circle over to the North End, Boston’s Italian neighborhood.  The food is devine and you’ll find perhaps the best cannoli of your life!  Don’t miss the Saint Days in late summer when the whole city comes to celebrate.

Hatch Shell Boston Esplanade

Finally, there are always festivals and special events going on in Boston.  A few that come to mind are concerts at the Hatch Shell on the banks of the Charles River, Free Friday Night Flicks and Harbor Walk Sounds at the Institute of Contemporary Art, as well as Scooper Bowl, Harborfest, Chowderfest, and too many to name.  With 54 colleges in the greater Boston area, there’s always a good time happening in the city.  Good sites for finding events and celebrations in Boston are and

Boston is one city that excites your senses and will enrich your life.

Photo Source:  Google Commons

Share This Story, Choose Your Platform!