A college town. The heart of the revolution. A sports fan’s heaven. An intellectual hub. Home to some of the best hikes in New England. These are just a few of the ways to describe Boston, one of America’s oldest and most iconic cities, which continues to transform itself throughout the years.
With one day in Boston, immerse yourself in the country’s rich history by visiting revolutionary landmarks and war monuments scattered all throughout the city. Step inside America’s very first park (Boston Common), ride on its first subway system (Tremont Street Subway), and wander the halls of the first public municipal library, the Boston Public Library.
Of course, a trip to Boston isn’t just about looking towards the past. You can thank its diverse and young student population for keeping the city on its contemporary toes. During a visit to Boston, you’ll find world-class museums, modern green spaces, visionary research facilities, and endless amounts of trendy restaurants, cafes, and bars, making it an inspiring destination for a romantic getaway on the East Coast.
Even if you only plan on spending a day in Boston, you’ll be able to experience all of the highlights of the city thanks to its easily walkable nature and condensed downtown area. Here is the ultimate one day in Boston itinerary.
Stroll Around the Boston Harborwalk
Start off the morning by walking along the Boston Harbor, the body of water made famous by the Boston Tea Party of 1773, which helped sparked the seeds of the Revolutionary War.
Spanning over 43 miles, the Boston Harborwalk allows you to take in picturesque views and discover up to eight different neighborhoods around the city, including Dorchester, the North End, South Boston, and Fort Point, where you can stop by the Children’s Museum or board a Boston Tea Party ship and reenact this pivotal moment in history by throwing some tea overboard.
Enjoy Breakfast at Beacon Hill
For a delicious breakfast, head to Beacon Hill, one of Boston’s most charming and exclusive neighborhoods. Walk around the cobbled streets and red brick buildings, which house award-winning restaurants, antique shops, and quaint bakeries.
Don’t miss strolling by Acorn Street, a highly photographed corner of the neighborhood, where ivy-strewn walls and historic row houses make for the perfect Instagram background.
Relax at Boston Common
Next to Beacon Hill, you’ll find Boston Common, America’s oldest park and the unofficial heart of the city. Founded in 1634, the park has been an important site throughout history and continues to be a popular space with locals, students, and tourists due to its central location and lovely scenery.
Relax under a weeping willow tree, spend some quiet time at Frog Pond, and stroll hand-in-hand with your loved one. If you’re looking for something a little outside of the box, board one of the quirky swan boats that are found in the lake at the Boston Public Garden.
Follow the Freedom Trail
One of the best ways to discover Boston and its storied history is by embarking on the Freedom Trail, a two-and-a-half-mile route that kicks off at Boston Common and visits 16 historical sites around the city.
If you’d like some direction, sign up for a private walking tour, where a guide dressed in an 18th-century costume will take you to landmarks that include the Bunker Hill Monument, the Old North Church (the oldest church in Boston and site of the “one if by land, two if by sea” lanterns), the Paul Revere House, and the site of the Boston Massacre.
You can also choose to walk the Freedom Trail at your own pace by following the red brick path outlining the way to each historic monument around the city. This way is preferable for families with kids or those who don’t like to be rushed.
Try Local Food at Faneuil Hall and Quincy Market
Stop by Faneuil Hall Marketplace, an outdoor promenade located near the waterfront, where you’ll find dozens of vendors, restaurants, and the famous Quincy Market colonnade. Enjoy local favorites like Boston baked beans, Boston cream pie, lobster rolls, and clam chowder at one of the food stands.
Watch street performers like jugglers, acrobats, and magicians entertain the crowds on the marketplace’s cobblestone streets. Squeeze in some shopping at the big-name retail stores and local, hand-crafted vendors.
Sip a Beer and Smell the Flowers at Rose Fitzgerald Kennedy Greenway
Burn off the lunch calories by making your way through the winding green trails of the Rose Fitzgerald Kennedy Greenway, a former elevated highway turned linear park that snakes through several neighborhoods of downtown Boston.
Throughout the one-and-a-half mile greenway, grab a snack at one of the many food trucks, take the kids for a spin on the carousel, enjoy a refreshing pint at an open-air beer garden, and admire the lovely flowers and plants in the surrounding gardens and meadows.
Catch a Game at Fenway Park
Even if you’re not a Red Sox fan, you’ll want to pay a visit to Fenway Park, one of the most famous baseball parks in the world. See why Red Sox fans are so devoted to their home team by catching a game with the 2018 World Series champions.
During the game, munch on a Fenway Frank, sing along to “Sweet Caroline,” the classic song played at the bottom of every eighth inning, and see if you can spot the single red seat amongst rows of green bleachers, which marks the farthest home run ever hit at Fenway Park.
Tour the Campuses in Cambridge
Feel like you’re a college student all over again by visiting the town of Cambridge, home to the venerable institutions of Harvard University and Massachusetts Institute of Technology. Admire the lovely bike lanes, spend some wandering the aisles of its indie bookstores, and sip a cup of coffee while surrounded by local Cantabridgians.
You can also spend some time touring Harvard’s Art Museums, which include masterpieces from several important periods of art history, and the MIT campus, where you’ll find futuristic buildings designed by Frank Gehry and I.M. Pei.
Enjoy the View at the Charles River Esplanade
Once you’re done exploring Cambridge, walk over to Charles River Esplanade, a picturesque stretch that runs alongside the river. Enjoy the pretty views by foot or on a bicycle. You can also explore the river itself by renting a canoe, paddle board, or kayak. If you’re in Boston during the summer, find out if there are any outdoor concerts or events taking place at the Esplanade’s Hatch Shell.
Spot Marine Animals at New England Aquarium
Both kids and adults will love an afternoon trip to the New England Aquarium, which attracts over a million visitors each year. The two major highlights are the four-story Giant Ocean Tank, which houses sea turtles, stingrays, and eels; and the Indo-Pacific Coral Reef, a 9,000-gallon habitat that stretches from the floor to the ceiling.
There are also exhibitions dedicated to the science of sharks; a marine mammal center, where you can watch seals jump over the water; a penguin exhibit; and a small touch tank, where young ones can pet starfish and lobsters.
Cruise Along the Boston Harbor
A few steps from the aquarium, you’ll arrive at Long Wharf, where you can board a sightseeing cruise around Boston Harbor, a wonderful way to admire views of the city’s skyline and learn more about the harbor’s colorful past.
Options include visiting the Boston Harbor Islands, whale-watching tours, and fall foliage cruises. For a truly spectacular time, board a sunset sailing around the harbor, where you’ll marvel at the multi-hued colors in the distance while cruising past the USS Constitution, the oldest naval vessel in the United States, and see her fire her canon and lower her flag at the end of the day.
Savor an Italian Dinner at the North End
Once you’re back on land and in the mood for dinner, head to the North End, Boston’s version of Little Italy. Grab a seat at one of the cozy trattorias and enjoy a delicious plate of pasta and a glass of red wine while you toast with your sweetheart. If you’re traveling with kids, rest easy knowing that the North End is home to delicious, family-friendly pizza spots.
Cap off your dinner with a stop at one of the neighborhood’s many gelaterias or bakeries and order a box of traditional cannoli. If you’re in town during the summer, don’t miss the parades, processions, and festivals that often take place during the weekends, where you can enjoy street food, games, and live music.
Now that you’ve read our one day in Boston itinerary, it’s time to start planning your next trip to the city with Celebrity Cruises. Spend a day there before boarding a cruise from Boston to Maine, Canada, Puerto Rico, and other exciting destinations.
Browse our Boston cruise itineraries and start planning your next vacation today.