Boston: The Ultimate Guide
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I have been going to New England for over 30 years and every time I go, I find new places to explore and have favorite places I always go back to. Boston is one of those places.
In this guide, we will focus on Boston, but if you have more time to explore New England, I recommend spending a couple of days in Boston and then heading to Bar Harbor. There are lots of beautiful stops you can make along the way. Check out my travel guide: Acadia National Park & Bar Harbor, Maine.
Every season in Boston is beautiful and has something special to offer. Visit in the Spring to see everything in bloom. Visit in the Summer to enjoy warm days and cool nights. The Fall foliage can’t be beat and seeing everything covered in a white blanket of snow in the winter is magical.
Boston is the capital of Massachusetts and the cultural and financial center of New England. It is a 393-year-old city steeped in history. It’s also home to the Boston Celtics, Boston Red Socks and Boston Bruins.
Getting There
If you fly to Boston, you’ll be flying into Logan International Airport. Two to three nights in Boston is a good amount of time to get the lay of the land. I would Uber or take public transportation to Downtown Boston. It’s only a time-minute ride from the airport to downtown. Boston is a very walkable city and it is expensive to park a car in the city.
Where To Stay
Each of these is centrally located and close to Boston Common.
Guided Tours
If you would like to take a guided tour to get the lay of the land, learn more about the history of Boston or to see something you otherwise wouldn’t get to see, check out these tours below.
Freedom Trail Walking Tour
Freedom Trail Pub Crawl
Food Tour of Boston’s Little Italy
Guided Seafood and City Tour
Ghost Tour of Boston’s Haunted Past
Whale Watching Cruise on a High Speed Catamaran
Guided Harvard University Walking Tour
Things To Do - For the History Buff
The Freedom Trail
The Freedom Trail is a 2.5-mile walk through the city that passes 16 historic sites. Keep in mind this is 2.5 miles, one way.
1. Boston Common and the Public Garden
Boston Common is the oldest public park in the United States, created in 1634. The Boston Public Garden was the first botanical garden in the United States. It also has a six-acre pond with swan boats that you can ride.
2. Beacon Hill & Massachusetts State House
Beacon Hill is an exclusive area of Boston with beautiful brick townhouses. It’s also where the Massachusetts State House is located and Acorn Street, which is one the most photographed streets in the country. I also love browsing the shops on Charles Street. The last time we were there, we got sandwiches to go from Tatte Bakery & Café and had a picnic in Boston Common, the oldest city park in the United States.
3. Park Street Church
Park Street Church was founded in 1809, over two decades after Massachusetts outlawed slavery, the church’s congregation was among the first to address anti-slavery on a national level.
4. Granary Burying Ground
The Granary Burying Ground is the third-oldest cemetery in Boston, founded in 1660. It is the burial location of Revolutionary War-era patriots, including Paul Revere, the five victims of the Boston Massacre, and three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine.
5. King's Chapel and King's Chapel Burying Ground
The King's Chapel Burying Ground was founded in 1630 as the first graveyard in the city, making it the oldest burial ground in Boston. It has many notable burials including, Mary Chilton and Plymouth Pilgrim and the first European woman to step ashore in New England.
6. Boston Latin School Site & Statue of Benjamin Franklin
The Boston Latin School was founded on April 23, 1635. It is the oldest public school in America. Five signers of the Declaration of Independence attended Boston Latin Benjamin Franklin, Samuel Adams, John Hancock, Robert Treat Paine, and William Hooper.
7. Old Corner Bookstore
The Old Corner Book Store was built in 1718 and is Boston’s oldest commercial building. It was once home to the publishing company that produced The Scarlet Letter and Midnight Ride of Paul Revere.
8. Old South Meeting House
The Old South Meeting House was built as a Puritan meeting house in 1729. It was the largest building in colonial Boston. It became the center of public protest meetings. This is where Samuel Adams gave the signal that started the Boston Tea Party December 16, 1773.
9. Old State House
The Old State House is the oldest surviving public building in Boston, built in 1713. It is now a history museum.
10. Boston Massacre Site
The Boston Massacre occurred when British Soldiers shot into a crowd of American colonists on March 5, 1770, killing 5 people and wounding 6 others.
11. Faneuil Hall
Faneuil Hall opened in 1742 and was a marketplace and meeting hall. It’s where Samuel Adams and James Otis gave speeches encouraging independence from Great Britain. Adjacent to Faneuil Hall is Quincy Market which is a historic food hall that was opened in 1826 with over 50 eateries and vendors.
12. Paul Revere House
The North End is Boston’s Little Italy and home to Paul Revere’s House from 1680. Hanover Street is a great place to get coffee and pastries or a delicious Italian dinner.
13. Old North Church
Old North Church was built in 1723 and is the oldest standing church building in Boston and a National Historic Landmark. Old North Church is significant because it was where Paul Revere began the midnight ride. On April 18th, 1775, Paul Revere began alerting the American colonial militia that the British forces were approaching. This was the beginning of the American Revolutionary War.
14. Copp's Hill Burying Ground
Copp’s Hill Burying Ground was founded in 1659 and is the second-oldest cemetery in Boston.
15. USS Constitution
The USS Constitution is the world's oldest commissioned naval warship still afloat. She was built in the North End of Boston and first launched in 1797. She is currently in the Charlestown Navy Yard.
16. Bunker Hill Monument
The first or final stop on the Freedom Trail, depending on which way you start, is the Bunker Hill Monument. This is where the Battle of Bunker Hill took place on June 17, 1775. This was one of the first major battles between the Red Coats and the Patriots in the American Revolutionary War. The monument has 294 steps to the top.
Grab a Boston City Pass Here for discounted entrance fees to 4 attractions.
Things To Do - With Kids
New England Aquarium
The New England Aquarium is a great stop, especially if you have kids. They have penguins, sea lions, harbor seals, rays and sea turtles just to name a few.
Boston Museum of Science
The Boston Museum of Science has more than 700 interactive exhibits, an IMAX® Dome screen, a Theater of Electricity, a planetarium, a butterfly garden and a 4D cinema.
Boston Children’s Museum
The Boston Children’s Museum is the second oldest children’s museum in the world, founded in 1913.
Boston Tea Party Ships & Museum
The Boston Tea Party Museum offers a multi-sensory experience with live actors, interactive exhibits, and full-scale replica 18th-century sailing vessels. Then visit Abigail’s Tea Room for some tea and scones.
Things To Do - For The Foodie
Massachusetts is known for its seafood like lobster, crab, oysters, New England Clam Chowder and scallops. Check out the Guided Seafood and City Tour . It's also the birthplace of Boston Cream Pie and Sam Adams Beer. Check out the Freedom Trail Pub Crawl.
The North End is Boston’s Little Italy. Hanover Street is a great place to get coffee and pastries at the popular, Mike’s Pasty or find a delicious Italian dinner. Check out the Food Tour of Boston’s Little Italy.
Things To Do - For The Shopping Enthusiast
Newbury Street
Newbury Street is located in the Back Bay area of Boston. It is a street lined with restaurants and high-end shops including Burberry, Chanel, Giorgio Armani, Cartier, Valentino and Restoration Hardware just to name a few.
The Prudential Center
The Prudential Center has over 70 high-end shops and eateries including Eataly, a 45,000-square-foot Italian marketplace with restaurants, take-away counters, and a cooking school. While you’re there don’t miss View Boston with 360 views of Boston from the top floor. They have yoga in the mornings and are open until 10PM so you can watch the sunset and grab a cocktail.
Things To Do - For The Sports Enthusiast
Fenway Park
Fenway Park is the oldest ballpark in Major League Baseball. If you’re a baseball fan, you can catch a Red Sox game or take a Guided Fenway Park Tour.
TD Garden
Catch a Boston Celtics or Boston Bruins game at The Garden.
There is literally something for everyone in Boston. I hope you love it as much as we do! If you have extra time and plan on exploring more of New England make sure to check out my travel guide to Acadia National Park & Bar Harbor, Maine.
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