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Boston may not be as overwhelming as NYC or have the a festive atmosphere of Miami, but it’s definitely a one-of-a-kind city with the chance to relive history, cheer for hometown sports, explore interesting museums and tour one of the most important universities in the world.

If you’re visiting Boston for the first time, you’ll definitely find Massachusetts’ capital fascinating. As one of the oldest cities in the country, it has played a prominent role in US history and it’s a great city to visit.

Renting a car in Boston is a great idea for exploring the surrounding areas and towns, and will make the following itinerary a lot easier, and far more flexible to do by yourself.

Remember to purchase a car rental damage insurance policy when renting a car in the US; with so many car rental insurance options available, look into the alternatives first and choose one that works better for you in terms of your budget and the coverage it offers.

During your stay in Boston you’ll discover plenty of things to see and do and, regardless of your interests, you’ll be fully entertained. However for the history buff in particular, there are some pretty remarkable attractions!

Things to Do in Boston for History Buffs

First, Book Your Hotel:

Freedom Trail

Boston RF

Many of the following historic attractions can be found along the three-mile Freedom Trail, so this seemed like a natural place to start! The trail leads tourists past and into 16 of Boston’s most significant historic sites and monuments.

You simply need to follow the line of red bricks in the sidewalk and footprints at street crossings and follow the hints! This is an interactive and interesting way to learn about the history of Boston and understand the important role it played in American history.

You can explore famous Revolutionary War and Colonial sites, as well as other attractions closely related to the country’s fight for liberty such as the USS Constitution.

You’ll also pass through beautiful and charming historic Boston neighborhoods such as Beacon Hill or the North End. The walking trail starts at the Boston Common (the oldest part in the United States) and the end of the path connects with Harborwalk, leading visitors to the USS Constitution.

Now that we’ve mentioned it twice, the USS Constitution is definitely a site not to miss; it is a wooden-hulled, three-masted heavy frigate of the United States Navy, and the world’s oldest commissioned naval vessel still afloat, open for the public to walk onboard.

Walking the whole Freedom Trail will probably take you between one and three hours, depending on how interested you are in American history. Don’t miss the North End to see Paul Revere’s House and the Old North Church!

It’s important to wear a pair of comfortable walking shoes. If you don’t fancy navigating the Freedom Trail on your own, many visitors find the walking tour offered by the XVIII-century costumed Freedom Trail Player tour guides are informative and entertaining and are an excellent introduction to the city’s revolutionary roots.

Faneuil Hall

Quincy Market Boston RF

Built by the merchant Peter Faneuil in the mid 1700s, Faneuil Hall is known by Bostonians as the “cradle of liberty”. This is a historic hall and marketplace, now an iconic place to eat and shop.

There are market stalls on the ground floor but the upper floor is a council chamber that in the XVIII and XIX centuries was the meeting place of revolutionaries and later of abolitionists. The fourth floor is home to the interesting Ancient and Artillery Museum.

Located in the heart of downtown Boston and along the Freedom Trail, it now encompasses the North Market, Quincy Market and South Market buildings as well. The building is still used as both a marketplace and as a place of political debates and it is one of the most popular tourist attractions in the city.

Faneuil Hall and Faneuil Marketplace include more than a hundred shops and restaurants, making it an ideal place to go shopping and grab a bite! Be on the lookout for street performers as well, especially in Quincy Market!

Museum of Fine Arts

Museum of Fine Arts Boston

The Museum of Fine Arts in Boston is one of the leading art museums in the United States and is renowned for its superb collection on ancient Egypt, Asian and Persian fine arts, works from the Middle East and Greece, and Impressionist paintings.

It has an American Wing completely devoted to American paintings, decorative arts, folk art, glassware, silver, furniture and design dating from pre-Columbian arts to the Art Deco and Modernist eras.

With its hundreds of galleries each filled with artistic treasures of all times, the Boston Museum of Fine Arts can keep you busy for a whole day. Fortunately, there are various dining options, specialized boutiques and performances offered for a great day in the museum.

Expect to find Egyptian mummies and pottery as well as other artifacts, African masks and African funeral artifacts and superb works of art including some by Georgia O’Keeffe, Picasso, Monet or Renoir.

If spending so much time at the museum feels overwhelming and too much to take in, remember that your ticket gives you a repeat free visit within ten days!

Image credit: Allie_Caulfield (CC BY 2.0) via Flickr

Boston Common and Public Garden

Boston Common RF

Boston Common is located in the heart of the city and it’s the country’s oldest park. It marks the beginning of the Freedom Trail, and is a large green area that locals enjoy all year round.

Adjoining is the Public Garden, America’s oldest botanical garden, home of popular modern bronzes such as a family of ducks. There are theatre and public performances held in Boston Common throughout the year, so check for events on the Government website.

It’s great for picnics and leisurely strolls and it’s perfect for families with young children (local children love to play at the Tadpole Playground and enjoy the sprays at the Playground Frog Pond).

You can ice skate, play softball or tennis or simply enjoy reading a book! Many famous leaders have delivered speeches at Boston Common and it played a prominent role in American history.

Old North Church and the North End

The North End is Boston’s Italian neighborhood and one of the oldest in the city. It’s where the activist leader Paul Revere lived during the times of the American Revolution.

You can visit his house or climb to the tower of Old North Church, where lanterns were hung in April 1775 to alert Paul Revere that British troops were headed to Lexington to arrest the patriot leaders and confiscate munitions supplies.

Tourists love going to the North End; not only because of its important historic sights but also because of its cheerful  and attractive Italian flare. There are plenty of Italian restaurants and cafeterias and it’s definitely a great place to eat a pizza or a delicious Italian cappuccino!

The Old North Church is probably one of the most visited historic sites in Boston. It came to fame in 1775 when the church sexton and the Vestryman Captain ascended the steeple with two lanterns to signal Paul Revere that the British were coming and thus the American Revolution was ignited.

It’s the city’s oldest surviving church and it’s one that the whole family will enjoy visiting. It is one of the most prominent stops along the Freedom Trail and home to a crypt, where many soldiers killed in the Battle of Bunker Hill lie.

The Paul Revere House

Paul Revere House RF

The Paul Revere House offers an interesting glimpse of what life was like in the late 1700s in Boston. Located on the Freedom Trail, it’s even filled with period pieces including fine silver.

Sweeping beams, original furnishing and spacious fireplaces will delight history fans. It’s the oldest house in downtown Boston and it was the home of silversmith and Boston patriot Paul Revere.

It was restored by Revere’s great-grandson in 1902 and six years later it was  opened to the public. Even though visitors are not allowed to take pictures inside, there are interesting souvenirs and mementos that can be purchased such as reproductions, educational material and prints.

USS Constitution and Bunker Hill

USS Constitution Ship Boston

USS Constitution is the oldest commissioned ship in the US Navy and it’s still commanded and crewed. It’s definitely one of the most interesting attractions in Boston and you definitely shouldn’t miss it.

Now open for guided tours, you’ll learn everything about the ship’s construction and action at sea. It’s berthed at Pier 1 on the Harborwalk and still sets sail every 4th July to commemorate America’s Independence.

Across the pier, the USS Constitution Museum has interesting interactive exhibits that provide the historical context and illustrate life aboard a naval vessel more than two hundred years ago.

It’s a very popular place among history lovers, military aficionados and boat enthusiasts. Its knowledgeable staff are always eager to share what they know about this ship with visitors, and this is a highlight in this already very interesting vessel.

Fun fact: Undefeated in 33 naval battles, the USS Constitution is currently the only active US Navy vessel to have sunk another ship in combat, including HMS Guerriere in 1812.

Image: U.S. Coast Guard by Petty Officer 3rd Class Andrew Barresi (CC BY 2.0) via Official U.S. Navy Page 

Climb the Bunker Hill Monument

Bunker Hill Monument Boston

Bunker Hill Monument marks the location of one of the first battles of the American Revolutionary War, the 1775 Battle of Bunker Hill. It’s one of the most historically meaningful places in Boston and it commemorates those who fought.

Image: (CC BY 2.0) via Flickr

Visit Harvard University

No visit to Boston would be complete without taking a tour of Harvard University. You can easily catch a subway out to Harvard from Downtown Boston, or drive yourself if you’ve rented a car.

The grounds of Harvard University are absolutely stunning: magnificent red brick buildings, gorgeous gardens and unique art! Founded in the early 1630s, it’s the oldest university in America.

Public tours will take you through different buildings and the history of the university. Then you can explore Harvard Square. It’s an offbeat and intellectual area with a mix of ages, languages and cultures.

There are plenty of independent bookstores, coffeehouses and cinemas on the campus, as well as the intriguing Semitic Museum with more than 40 thousand artifacts in archaeological expeditions to Israel, Jordan, Egypt, Syria and Tunisia.

The Harvard Museum of Natural History is also worth a visit, where you can explore more than 12 thousand specimens: dinosaur fossils, gemstones, meteorites, animals on display from around the globe, a beautiful gallery of glass flowers and even an active bee colony!

Walk Along Boston Waterfront

Boston Waterfront RF

The Boston waterfront offers spectacular views of the city skyline. To enjoy the best views, start near the New England Aquarium and follow the water to the front of the John Joseph Moakley US Courthouse.

As Boston is surrounded by water on three sides it offers visitors a huge variety of waterfront park and areas, river and harbor cruises. For instance, Charles River and the Esplanade is a long linear park only accessed by special footbridges and a favorite amongst walkers and runners.

Walk along the Harbor and follow the Waterfront Trail which passes along the edge of wharves, piers, beaches and shoreline. There are restaurants, fashion stores, museums, art galleries and hotels for an entertaining walk!

The area is home to Boston’s most vibrant neighborhoods and there’s always something interesting to see and do. Boston  Harbor, filled with fishing boats, whale-watching vessels and sailboats is also a magnetic attraction.

Don’t miss the dozens of Boston harbor islands; head to Georges Island, home of the Civil War-era Fort Warren or to the beautiful beaches and hiking trails of Spectacle Island; both a short ferry ride away from downtown Boston.

Boston Tea Party Ships & Museum

Boston Tea Party RF

The Boston Tea Party served as the famous catalyst for the revolutionary movement in Massachusetts, and this is one of the most important events in American history.

At the Boston Tea Party Ships and Museum you’ll be able to learn how a few hundred colonists in Boston dumped more than 300 chests of tea into the harbor in mid December 1773 thus kicking off the push for independence in Boston.

You’ll be able to step into the past by participating in activities on the three replica ships and even get to toss some tea overboard. It’s a fantastic, interactive and immersive experience that both children and adults enjoy.

This floating museum is made up of high tech interactive exhibits, restored tea ships, captivating documentaries about this famous event and knowledgeable actors that make the representations even more appealing.

There’s also a well stocked gift shop and a charming café where you can try delicious treats.

Boston is a modern city, though bursting at the seams with living history, and stories from the past. Where will you start?

Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind Waking Up Wild; an online magazine dedicated to opening your eyes to the wonders of the wild & natural world.

Having visited 50+ countries across all seven continents, Megan’s travels focus on cultural immersion, authentic discovery and incredible journeys. She has a strong passion for ecotourism, and aims to promote responsible travel experiences.



  1. Interesting post. I’ve been to Boston only once for work, and always wanted to go back. Now I know that I must go back :)

    • Glad the post was helpful Moshe! Definitely, it’s one of those cities that definitely deserves some dedicated time for exploration – perfect excuse to plan a trip back :)

      Thanks for reading :)

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