Best Sightseeing in Boston

Savvy Boston Sightseeing = History, Tours, Museums, Exercise and Education

Boston is a large city that feels much smaller than it is. Maybe it's because it is easily walkable or because you'll find familiarity in the sites, be it from history books or media depictions. Either way you'll feel at home checking out Boston's 10best.

The Public Garden is a must any time of year, the landscape changes to reflect the seasons and offers visitors the chance to stroll, picnic, or take a whirl on the Swan Boats. Plus, the Public Garden offers some of the best photo opportunities Boston has to offer.

A trip to Castle Island Park combines history with outdoor fun (great for a walk, to enjoy the beach or let the kids loose at the playground).

If you are an animal lover, the Franklin Park Zoo has 100 years of rave reviews to entice you through its gates, and is one of the best stocked zoos around. 

Those seeking an interactive experience with a historical twist can be found at the Tea Party Ships and Museum where your guides will take you back to the night the tea was dumped in the Harbor and even have you try your hand at tossing tea.

But your one stop shop for seeing it all is the easy to follow Freedom Trail; taking you all around Boston with well marked stops at the most historical locations throughout the city. 


Harvard University is America's oldest University, Founded in 1636 it was named for its first patron, Reverend John Harvard. Enjoy a stroll around the grounds on take the free, guided historical tour of the campus and its most famous landmarks. This student led tour offers an overview of the history of the university while stopping at sites like the Widener Library, Memorial Church, University Hall, Fogg Museum and the John Harvard Statue. With a location like Harvard, visitors can easily enjoy all Harvard Square has to offer when done touring the University grounds. Here you'll find an eclectic mix of those who call Cambridge home roaming the streets including talented street performers, and students enjoying area restaurants, bars, music venues and stores.

Recommended for Sightseeing because: Harvard University is America's oldest, and with its bustling Harvard Square location allows for a full day/night of exploration.

Jessica's expert tip: Harvard Square is built around the university. Be sure to explore the Square and enjoy food, drinks and entertainment at local hot spots.

Read more about Harvard University →

Part of the Emerald Necklace, famous for the loop of green space that circles the city, is the Franklin Park Zoo. You can spend the day roaming the grounds of the zoo and checking out the many species housed within. Kids will love the open space, and modern playground, as much as they'll enjoy seeing what lives in the cages on site. One of the best Zoos around, the Franklin Park Zoo is worth seeing. Franklin Park Zoo is a 72-acres packed with wildlife that has been in Boston's historic Franklin Park for one hundred years! Along with their usual animal exhibits, the Zoo often holds special events, celebrations, and wildlife exhibits.

Recommended for Sightseeing because: The Franklin Park Zoo is one of the best in the area and offers a full day of family fun.

Jessica's expert tip: The Franklin Park Zoo is a great place to visit, but it is THE attraction within its neighborhood., Before and after Zoo plans should take place elsewhere.

Read more about Franklin Park Zoo →

Boston Public Library
Photo courtesy of iStock / gregobagel

The first public library in the United States, this Boston institution not only houses a wide variety of literary works (over 6 million), but also displays the creations of visual artists. Many works remain permanently in the library while others are part of a constantly changing exhibit of sculpture and paintings. The books may draw you through their doors, but the beauty of the building itself will have you exploring for hours. When you're done, enjoy lunch in their restaurant or flip through your latest find in the cafe. In nice weather, go enjoy the peace and serenity of the newly restored courtyard. Rare books and manuscripts are also available at this awe inspiring facility.

Recommended for Sightseeing because: A library complete with art, an inviting courtyard and elaborate architecture at the Boston Public Library are offered.

Jessica's expert tip: A visit to the library is free and has as much to offer as most art museums; pop in for a bit while in Boston's Back Bay.

Read more about Boston Public Library →

Castle Island Park
Photo courtesy of Castle Island Park

Castle Island is a twenty two acre urban park located along the waterfront and home to Fort Independence. With many paths for walking, biking or running as well as a playground and beaches, Castle Island allows visitors to see a Boston attraction and relax on one of their urban beaches that draw crowds of locals during the summer. With a clam shack on site (Sullivan's) you can stay through lunch and enjoy all that castle Island has to offer including the excellent view of Logan making it the perfect place for plane lovers to watch both take offs and landing.

Recommended for Sightseeing because: Castle Island is a 22 acre urban park that is home to fort Independence which played a crucial role in America's history.

Jessica's expert tip: Free and open year round, Castle Island gets crowded during summer months, and parking get difficult.

Read more about Castle Island Park →

Board a WWII-style amphibious landing vehicle, and get ready for a thrilling ride that's sure to make a splash. Children of all ages will love learning about Beantown from a knowledgeable "ConDUCKtor" who makes history quite comical with the addition of humorous stories to liven things up. The tour covers historical sites of the city and is one of the best ways to get an overview of major attractions. Start out on land from one of their three locations then plunge into the Charles River for a unique view of Boston. Kids will especially enjoy quacking at passersby and may even get the chance to drive the DUCK while water bound.

Recommended for Sightseeing because: Boston Duck Tours are fun way to do sightseeing without putting in much legwork; climb aboard and enjoy the "cruise".

Jessica's expert tip: The tour the locals love is a MUST for visitors. ConDUCKtors are fun, and make sure you enjoy the ride. You may even get a turn a wheel while in the water.

Read more about Boston Duck Tours →

Boston Public Garden

Take a leisurely stroll through the oldest botanical garden in the United States and get a feel for Boston's charm and grace. 1877 marks the start of the Garden's fame for the Swan Boats that float along the pond when the weather warms; a necessary ride for the kid in all of us. The Swan Boats do not get all the attention, as the grounds truly are a sight to hold. Pack a picnic and sprawl across the lawn to enjoy the beauty of this inner city treasure. Year round, the beauty of Public Garden shines, and makes for excellent photo opportunities.

Recommended for Sightseeing because: Stunningly beautiful in late spring when the Public Garden is in full bloom, you'll find historical spots hidden among the beauty.

Jessica's expert tip: Ideally located in the heart of Boston so that you can integrate a visit to the Public Garden with other sightseeing in the same day (the Boston Common perhaps).

Read more about Boston Public Garden →

Roam the galleries or watch a show in a waterfront building that is as beautiful as what is housed inside. The modern art is an eclectic mix of what may sometimes seem to be mayhem. Funky fun displays rule the roost at this cutting edge art museum. Kids will marvel at the art inside because unlike traditional museums some of the stuff at the ICA looks more like stuff that's familiar. The ICA offers playdates every month that maximize your time inside. These days are designed to bring fun to art and the free family admission on these days includes hands-on art-making, performance, family gallery tours, and films. The ICA also has a fourth floor area designed for further exploration, ideal for non-playdate days.

Recommended for Sightseeing because: Fun, funky contemporary and shows collide under the roof of the ICA where the art lover can get an eyeful of something new,

Jessica's expert tip: When you've had your fill of what's inside, exit and enjoy the view from the Harborwalk; one of the city's best!

Read more about Institute of Contemporary Art/Boston →

Fenway Park

Boston fans are crazy about baseball. Ask many and they will claim it as their religion, and offer Fenway as their place of worship. The energy of the game is infectious and whether you are a Sox fan or routing for the opposing team, you'll find it hard not to get sucked into the enthusiasm. If a game is out of reach, or you want to get a good look inside this registered historical landmark, enjoy a tour. This in depth inside look at one of baseball's most beloved ballfields will have you places you only dreamed you'd see, as well as in the hardest seats to score for an actual game.

Recommended for Sightseeing because: Fenway Park is America's oldest Major League stadium and home to the legendary Green Monster, one of the hardest homer's to hit in the MLB.

Jessica's expert tip: Game day tickets can be hard to come by, if you don't luck out with seats take a guided tour to get inside the gates.

Read more about Fenway Park →

Boston Tea Party Ships & Museum
Photo courtesy of Boston Tea Party Ships & Museum

It was not just one night that led Patriots to take matters into their own hands to begin a fight for freedom, it was the continued lack of freedoms and representation that brought about the Tea Party and led to a full scale war. A visit to the Tea Party Ships and Museum lets you can relive the catalyst to the American Revolution and see memorabilia from the time and event. The interactive tour begins with a town meeting, takes you aboard a ship to toss tea into the Harbor then concludes with oral reports and a movie about the time period.

Recommended for Sightseeing because: The Tea Party Ships and Museum brings this event to life. You'll reenact the Tea Party with actors dressed in period garb.

Jessica's expert tip: Make time to have tea in the tearoom after your interactive visit.

Read more about Boston Tea Party Ships & Museum →

Boston's Freedom Trail
Photo courtesy of iStock / diegogrand

The best way to see Boston. Starting at the Boston Common, but easily be picked up at any point along the way, the Freedom Trail offers historical insight into the city and its surroundings. Easy to hop on and off, the Freedom Trail weaves throughout the city and highlights some of Boston's most special places. Enjoy all or part of this "map". Guided tours are available for a fee, but the best way to explore is on your own. Your walk will take you to such sites as: Boston Common Massachusetts State House Park Street Church Granary Burying Ground King's Chapel King's Chapel Burying Ground Benjamin Franklin Statue & Boston Latin School Old Corner Book Store Old South Meeting House Old State House Site of Boston Massacre Faneuil Hall Paul Revere House Old North Church Copp's Hill Burying Ground Bunker Hill Monument USS Constitution

Recommended for Sightseeing because: The Freedom Trail gives visitors a "map" of Boston's best sites and lets you easily explore the rich history that helped build America.

Jessica's expert tip: Put on your walking shoes! This tour will have you all over the city.

Read more about Boston's Freedom Trail →


Meet Jessica Polizzotti

Born and raised in Boston, Jessica knows her city like the back of her hand.  Always looking to uncover something new, Jessica keeps up on the latest and greatest Boston offerings. 

Although...  More About Jessica