10 Things to Do for Couples in Boston

I was born and raised in Rhode Island and then spent 20+ years as an adult living in New Hampshire. So I know Boston pretty well, and in my opinion, it’s one of the best and most interesting walking cities and one of the most bike-friendly cities in the US (driving is a whole different matter!). There are lots of things to do for couples in Boston!

It’s one of the most historically important cities in the United States, from the Puritans founding the city in 1630 to the many sites associated with the struggle for Independence along the legendary Freedom Trail.

Boston is a culturally rich waterfront city and foodie haven, with the best cannoli on the Earth (yes, including Italy, I’ve had both) to its iconic Irish pubs, and world-class Fenway Park, home of the Red Sox baseball team.

And don’t forget to try the legendary Dunkin Donuts coffee, the best coffee in the United States, located on every street corner, accompanied by either a maple frosted doughnut or (duh) a Boston cream doughnut.

Boston at a Glance

Population: 654,776 (2021)
Founded: September 7, 1630
Sales tax: 6.25% avalara.com
Demonym: Bostonian
Known for: Boston Tea Party; birthplace of American Revolution

Here are our favorite things for couples in Boston.

10 Museum of Science

Daderot, Public domain, via Wikimedia Commons

While kid-friendly, the Museum of Science is not just for children. Located on the Charles River, this huge institution is jam-packed with cool things to see and do. The museum contains thousands of displays and artifacts, as well as interactive and temporary exhibits, making it perfect for visitors of all ages and interests. There’s also an IMAX theater, a planetarium, and a butterfly house.

9 USS Constitution

The USS Constitution, aka “Old Ironsides” is legendary for its role in the War of 1812, famous for destroying five British and capturing many others. Sitting in the Charlestown Navy Yard in Bunker Hill, the ship is one of the top points of interest in Boston for history buffs. It’s also the oldest commissioned ship in the entire US Navy.

8 Boston Harbor

Historic and beautiful Boston Harbor (aka the Seaport District) was made famous for the massive amounts of tea dumped in its waters during the infamous Boston Tea Party, making it one of Boston’s top tourist attractions.

The area around the harbor has lots of cafes, restaurants, and bars. Visitors can explore the harbor on a sightseeing cruise, or on a stroll around the Harborwalk that winds around the coastline.

The harbor is especially lovely at sunset and dusk.

7 Faneuil Hall & Quincy Market

Combine your love for history with your love for shopping at the Faneuil Hall Marketplace. The area encompasses four buildings, the Faneuil Hall, North Market, South Market, and Quincy Market, this historic marketplace is full of unique shops, chain stores, street performers, and tons of food stalls and restaurants.

Faneuil Hall is one of the city’s most important historic sites. Located in the center of the city, this Boston institution was integral to the America’s independence process and played a part in Boston’s Underground Railroad network. Nowadays, Faneuil Hall is an entrance to bustling activity of the marketplace.

Quincy Market, next to Faneuil Hall, is one of the largest food halls in the US. There are a ton of restaurants where you can watch the world go by as you eat, as well as small souvenir shops and carts. If you prefer to eat on the go, there are vendors and food stalls to grab a quick bite.

6 Trinity Church

Trinity Church, located in the Back Bay neighborhood, is a stunning Episcopal church founded in 1733. The congregation currently stands at approximately 4,000 households.

The church is recognized as a National Historic Landmark building, considered by members of the American Association of Architects as one of the US top 10 buildings.

5 Theater District

Gabriel Saldana, CC BY-SA 2.0 via Wikimedia Commons

The Nutcracker, Swan Lake, Phantom of the Opera, Les Miserable, Miss Saigon, Blue Man Group. These are just a few of the Broadway shows, musicals, and ballets I’ve had the pleasure to see in Boston over the decades.

Originally opened in 1925, the Wang Theatre is pretty much an institution of the city and is my favorite. The lobby interior is magnificent, dripping with decadent chandeliers and so much gilded gold leafing that it has the vibe of a European palace. Inside the theater itself is also stunning.

4 Fenway Park

Whether you’re a baseball fan or not, you’ve got to visit the home of the iconic Boston Red Sox at Fenway Park. Built in 1912, Fenway Park is America’s smallest ballpark and oldest baseball franchise still in use.

Go to a game, but be forewarned…Boston fans are fiercely loyal can pretty rabid! When they are playing their nemesis, the Yankees, the competitiveness is absolutely surreal. You’ll be surrounded by a sea of Red Sox apparel and rabid, screaming fans. The iconic point is when they play “Sweet Caroline” and everyone joins in singing the beloved song. What does this song have to do with baseball? I have no idea, but I’ve enjoyed the tradition every time.

Be sure to grab a picture of the 37-foot tall left field wall popularly known as the Green Monster.

If it’s off-season, you can take a guided tour around the stadium to get the history and details of the inner workings and see some of the trophies and exhibits.

3 Boston Common/Public Garden

Established in 1634, Boston Common/Public Garden is famous for being America’s first public park. Visitors strolling the gardens can see beautiful nature such as lakes, lush trees, and colorful flower gardens. From mid-spring through mid-fall, visitors can take a 15-minute ride on the iconic swan boats.

Spanning over 50 acres, in spring, Boston Common is a great way to escape the chaos of the financial district in which it’s located. In spring, the gardens start to blossom leading to full bloom in summer. In fall, visitors can experience the vibrantly colored leaves that New England is so famous for. Winter is perfect for ice skating on Frog Pond.

The Public Garden is where you’ll find the “Make Way for Ducklings” statues celebrating Mr. and Mrs. Mallard and their eight offspring made famous by Robert McCloskey’s famous children’s book.

Sometimes live performances take place in Boston Common.

2 North End

I am always very excited at the prospect of going to the North End, aka “Little Italy.” I kid you not, the best Italian food I’ve ever had is here – including Italy which I’ve also visited more than once. Exploring the North End is one of the best things to do for couples in Boston and a great date night option.

Your tastebuds will thank you. Small family restaurants serve homemade pasta with any kind of sauce you choose. You can also find great seafood like clam “chowdah,” “lobstah” rolls, fish and chips, and oysters, in the North End, too…after all, it is New England.

Don’t forget the cannoli – again, the best in the world (Sicily is a close second). There’s an ongoing challenge here regarding who has the best cannoli – Mike’s Pastry Shop or Modern Pastry Shop. I did a blindfold challenge, and the results were not what I had anticipated. You can read the results here: “Boston’s Great Canoli Challenge.”

1 The Freedom Trail

The Boston Freedom Trail is the #1 most popular thing to do in Boston, and for good reason. Visitors get the chance to walk through history, following in the footsteps of some of the founders and heroes of our great nation.

This iconic 2.5-mile red brick path will take you past 16 historically significant sights important to American freedom and civil liberties, from Boston Common to Bunker Hill, winding through several famous historic Boston neighborhoods – Beacon Hill, the North End, and Charlestown. You can either go on a walking tour with a guide in period costume or discover it at your own pace by following the red line that marks the route. The Freedom Trail Foundation offers a free, downloadable map to guide you and give a bit of background.

Below are a couple of the most important highlights along the trail, along with #3, #7 and #9 above.

Paul Revere House

Located in the North End, the Paul Revere House is a spectacular living museum that has been meticulously preserved to look like it did in the late 1700s.

The former home of the legendary revolutionary is fitted out with period furniture, fine silver, and historic fireplaces.

It was in this building that Paul Revere warned Samuel Adams and John Hancock that they were about to be arrested by the British, giving them the necessary time to hide and elude them. The Revere house is considered to have been crucial to the success of the revolutionaries against the British.

Old North Church

Located in the North End, the Old North Church, built in 1723, is an Episcopal mission church, the oldest standing church building in Boston, and a National Historic Landmark. Old North Church is famous for its role in Paul Revere’s midnight ride on April 18, 1775, where he allegedly cried out, “The British are coming! The British are coming!”

You can get a nice view of the Old North Church by walking the treelined boulevard featuring a bronze statue of Paul Revere.

Old South Meeting House

The Old South Meeting House, built in 1729, is a historic Congregational church building located at the corner of Milk and Washington Streets in the Downtown Crossing area of Boston. It gained fame as the organizing point for the Boston Tea Party on December 16, 1773. Thousands of patriots gathered at Old South Meeting House to debate the controversial tea tax. At the end of the debate, Samuel Adams initiated the Boston Tea Party.

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About the Author

Patti Morrow is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and the southern travel blog Gone to Carolinas. TripAdvisor called her one of the “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.

She is also the star of the upcoming TV series “Destination Takeover” which is scheduled to premiere in the next few months.

Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal. She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.