Tours & Itineraries historic landmarks itinerary US > Eastern Massachusetts > Boston

36 Hours In Boston, Massachusetts

Anne Marie
Published Dec 28, 2018

There are many cities where visiting for only 36 hours would be a hassle. Either they are too spread out, or the lines at landmarks and attractions are too long. Boston, Massachusetts, is the opposite: it’s a city where you can cover a lot of ground in a short time! Its compact downtown area makes walking everywhere a breeze, and the Freedom Trail makes it easy to stop by all the historical spots. Boston’s historical significance is a major reason to visit the city: as one of the centers of the American Revolution, there are a lot of landmarks that predate America’s founding. However, this smaller city has just as much cosmopolitan flair as its larger counterparts, with award-winning restaurants and shopping options abound. If you’re planning a quick visit to Beantown, check out this itinerary for 36 hours in Boston!

Day 1: Afternoon - Start your trip off with a Boston Harbor USS Constitution Cruise (from USD 24)

Boston’s waterfront location means that a boating excursion is a must during your visit. Hop on to Get Your Guide’s Boston Harbor USS Constitution Cruise to see many of the city’s prominent landmarks! The cruise leaves from Boston’s Long Wharf and lasts just under an hour. The focus of the cruise is the USS Constitution, a ship that dates back to 1797 and played an important role in the War of 1812. Other landmarks you’ll pass by include the Bunker Hill Monument, Boston Tea Party Boat, and Old North Church. The tour is fully narrated and things you learn about Boston’s history will set a good tone for your visit!

Boston Harbor USS Constitution Cruise

Duration Wheelchair accessible

Rating 4.4 / 5

Number of Reviews 32

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Day 1: Evening - Check out the Old North Church and make your way to the North End for dinner

After the cruise, continue your tour of old Boston with a visit to the Old North Church. This church is famously situated where two lanterns were hung in 1775 after Paul Revere’s midnight ride. The lanterns symbolized that the British army was invading by sea, giving the Patriots an opportunity to prepare before the battles at Lexington and Concord. Today, the church is an enduring symbol of the American Revolution and Boston’s integral role in the country’s freedom. It is the oldest standing church in Boston and the inside looks like it would have at the time of Paul Revere. The Old North Church is located in Boston’s oldest neighborhood, the North End. It is full of windy cobblestone streets, skinny wooden houses, and delicious smells—in addition to being the city’s oldest neighborhood, it is probably the most delicious! Italian immigrants flooded the area in the early 20th century and dozens of Italian eateries remain in the area today. This is the perfect place for dinner, where you can get everything from a fancy meal to simple slices of pizza. If you’re not too full after, be sure to hit up one of the local pastry shops for dessert. Bova’s is a small, no-frills eatery that serves delicious cannoli, lobster tails, and more—and it’s open all night, so you can satisfy those late-night sugar cravings!

Old North Church

Address: 193 Salem St, Boston, MA 02113

Hours: 9 am to 6pm

Website: Old North Church

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Day 1: Night - Walk past the Paul Revere House and head into one of the bars in the area for a drink

After your meal, walk off some of that pasta by strolling around the North End. It’s a charming neighborhood with warmly lit streetlights and the sounds of accordions in the air. Though all of the homes look old-fashioned, there is one that looks even older than most: the Paul Revere House. This gray, wooden house is where Paul Revere lived from 1770 to 1800, during the time of his famous midnight ride. Though it has gone through several renovations since it was built in 1680, it still stands today as the oldest house in downtown Boston! If you still have a little energy left in you, make a little midnight ride of your own to check out the city’s nightlife. Nearby Faneuil Hall has many watering holes that attract tourists and locals alike. For shared Scorpion Bowl drinks, dancing, and karaoke, head to Hong Kong. If you’re seeking a quieter end to the evening, walk a little farther away from Faneuil Hall to Granary Tavern. This rustic bar with brick walls and wooden seating is a fitting vintage setting to this history-filled day.

Paul Revere House

Address: 19 N Square, Boston, MA 02113

Hours: 9:30 am to 4:15 pm

Website: Paul Revere House

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Day 2: Morning - Visit the Boston Massacre Site and wander to the Old City Hall

Start your next morning in Boston with another dose of American Revolutionary history. The city is the site of the Boston Massacre, an altercation that took place between Patriots and British soldiers in 1770. During the clash, British soldiers killed five Bostonians, which further fueled tension between the groups and caused the British troops to evacuate Boston for four years. Today, the massacre site is marked by a circle of cobblestones outside of the Old State House. The Boston Massacre site is one of many historic landmarks along the Freedom Trail, a trail of red bricks that winds through downtown. Follow the bricks to your next stop, the Old City Hall. This beautiful building, with tall columns separating arched windows, was the city hall from 1865 to 1969. The land the building sits on is also where Boston’s oldest public school once stood, with attendees like Benjamin Franklin and Samuel Adams. Today, the Old City Hall is home to office spaces and a steakhouse.

Boston Massacre Site

Address: Corner of State and, Congress St, Boston, MA 02109

Website: Boston Massacre Site

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Day 2: Afternoon - Check out the King's Chapel and Old State House Museum

Continue following the Freedom Trail to your next stop: King’s Chapel. This stone church dates back to 1754 and contains a bell that was cast by Paul Revere himself in 1816. You can visit the interior of the church for a guided tour, which takes place hourly Friday to Monday. The Bells and Bones Tour explore the church’s crypt and the bell tower, and the Art and Architecture tours explore the two floors of the sanctuary. Once you’ve wrapped up at King’s Chapel, follow the red bricks a few blocks to the Old State House. Built in 1713, this is the oldest public building that still stands in Boston today. It has been named one of the most important public buildings in Colonial America because it was the site of important political and civic meetings and discourse. It is where the Massachusetts Constitution was drafted, where the Declaration of Independence was proclaimed to Bostonians gathered below the balcony, and where the first Massachusetts state government met after the Revolution.

Old State House

Address: 206 Washington St, Boston, MA 02109

Hours: 9 am to 5 pm

Website: Old State House

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Day 2: Evening - Have dinner in Beacon Hill

After a long day of being on your feet, you’ll be more than ready to sit down and relax for a while. Use the last of your energy to walk over to Beacon Hill, one of Boston’s most charming and elegant neighborhoods. Stately brownstones line the cobblestone streets and there are many cute shops to peruse. Beacon Hill is also home to some of the city’s finest dining. If you feel like treating yourself, book a seat ahead of time at No. 9 Park. This is the flagship restaurant of chef Barbara Lynch, a Boston native who has won multiple awards and heads a group that runs seven restaurants in the area that consistently win best restaurant distinctions. The dishes are simple but flavorful, influenced by regional Italian and French Cuisine. Another great pick would be the less-expensive but just as classy 75 Chestnut. This restaurant is located in a cozy brick building and features classic dishes, including New England favorites like clam chowder.

No. 9 Park

Address: 9 Park Street, Boston, Massachusetts

Hours: 5 pm to 10 pm

Website: No. 9 Park

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Day 2: Night - Head to the Boston Common for an after-dinner stroll

Unless you’re eager for another night out at the bars, consider taking a relaxing post-dinner stroll around the Boston Common before you retire for the night. This is the city’s largest park, and it is the United States’ oldest! It dates back to 1634 and has served as a burial ground and a Revolutionary War camp in its past. Today it is a park of rolling green fields and shady trees, the perfect place to relax on a lawn or a bench on a mild evening. It sits at the foot of the Massachusetts State House, which looks just as pretty by night with spotlights illuminating its shiny gold dome. The Common is adjacent to the Public Garden, another pretty park which has a pond where ducks and swans can be spotted in the warmer months.

Boston Common

Address: 139 Tremont St, Boston, MA 02111

Website: Boston Common

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Day 3: Morning - Explore Back Bay's eclectic range of cafes and restaurants for brunch


For your last few hours in Boston, why not treat yourself to a delicious brunch? Back Bay, the neighborhood located to the west of the Boston Common, is full of many delicious options that range from casual to fancy. For an upscale brunch experience, head over to Sonsie on Newbury Street. This restaurant is inspired by a French bistro, and in the summer months, they open their front doors wide so diners can eat close to the street. The menu ranges from French-inspired breakfast foods to classic American dishes, and they have a great cocktail list, too. If you’re looking for a more casual and unique brunch spot, head across the street to Trident Booksellers and Café. This charming café is located on the first of two floors of a bookstore. They serve delicious meals and coffee, and you should definitely peruse the shelves before or after you eat. After you’ve had your brunch, be sure to leave a little time to wander around Back Bay. Between Newbury and Boylston Streets, this is Boston’s major shopping destination.

Trident Booksellers and Cafe

Address: 338 Newbury Street Boston, MA 02115

Hours: 8 am to 12 am

Website: Trident Booksellers and Cafe

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A quick taste of Boston

You could spend years in Boston and never tire of the city. It is full of things to do and places to see, and it is a city that is constantly changing. Though new restaurants and bars are constantly popping up, the other great thing about Boston is that much of it stays the same. Some of the buildings in this city date back hundreds of years, yet still manage to blend in with the new places around them. Whether you are returning back to Boston after being away, or this short visit is your first introduction to the city, it’s a charming place that is bound to bring you back again.

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Anne-Marie works in publishing by day and aspires to travel as much as she can. While she has not yet seen the whole world, she's eager to learn and write about it!

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