How to Spend Two Days In Boston

Quick trips can feel limited. Between travel time, settling in, and making decisions, sometimes spending the money on a weekend away doesn't feel worth it. If planned well, you can pack quite a bit in two days, and Boston offers just enough versatility – and walkability – to make it work. While a week in Boston is even better, if two days are all you have, the city is laid out beautifully to make it possible.

Deciding on where to stay will make the most significant impact on what should fill your itinerary. This two-day guide works great if you’re staying in the North End, Back Bay, or Beacon Hill neighborhoods – or at least within that relative area. One fantastic option is The Boxer Boston, a boutique hotel located in an old flatiron building on the edge of the North End. It’s nestled in a prime location close to Beacon Hill, the Back Bay, and Boston Common, saving valuable time during shorter trips. The Boxer has an industrial-chic aesthetic with modern, masculine, and artsy details. The staff is friendly and knowledgeable about the city, and the rooms are spacious, clean, and, most importantly, comfortable. Bikes are available to rent for those looking to cover more ground than walking allows.

With that settled, let’s get on with the schedule. Shall we? Day one is full of historical sites that everyone should see at least once in Boston. With many locations along Boston’s Freedom Trail in the North End, it’s only natural for us to start there. Later that day, we head to the historic Faneuil Hall. On day two, we dive into Boston’s iconic outdoor spaces and shopping district, a charming old neighborhood, and a 100-year-old map (trust us on this one). In case of inclement weather, we have a great backup option to spend time indoors that should be on any itinerary with a little more time. 

Let’s dive in…

Day 1: The Historic North End, Freedom Trail, and Faneuil Hall 

So much of Boston’s history can be found throughout the streets of the North End. Many of the stops on the Freedom Trail are in this neighborhood, along with some of the best Italian food and bakeries, oldest pubs, and more. The North End provides a unique opportunity to knock off many of Boston’s top spots within a few hours and all on foot! A quick tip: while a good part of the neighborhood can be seen walking down Hanover Street, it’s a good idea to veer off a few side roads. Salem Street, for example, has a few hidden gems and great photo opportunities. 

Kick off the day with coffee from The Thinking Cup before making your way through the cobblestone streets. The 17th-century buildings are home to The Bell & Hand, the country’s oldest, continuously operating tavern, and Union Oyster House, Boston’s oldest restaurant. If these brick walls could talk, we can only imagine what they’d say. Keep the historical adventure going by visiting stops along the Freedom Trail, a group of sites spanning a 2.5-mile route in downtown Boston. Explore the Paul Revere House, Old North Church, Faneuil Hall, and Copp’s Hill Burying Ground, all within walking distance. 

Tucked away on one of the many cobblestone streets, the Paul Revere House was the historical figure’s home during the Revolutionary era. The old colonial house is preserved to represent what life would have looked like while the Revere family lived there. It’s one of Boston’s oldest buildings and one of the few remaining 17th-century homes in an urban area. Also related to Paul Revere, the Old North Church is associated with his midnight ride. The oldest standing church building in Boston, the Old North was erected in 1723. 

With the North End at the heart of Boston’s old Italian community, it’s no surprise that there’s a fantastic food scene. Stop at Galleria Umberto’s for lunch and enjoy a slice of Sicilian-style pizza followed by a massive cannoli from Mike’s Pastry. Enjoy both while taking in some of the best views of the Boston skyline in North End Park. After lunch, head to Faneuil Hall Marketplace for some afternoon shopping. 

Faneuil Marketplace is comprised of the historic Faneuil Hall, Quincy Market, North Market, and South Market. The promenade features cobblestone pedestrian roads plus live music and entertainment year-round. Faneuil Hall has been known for a long time as Boston’s central meeting space. Meetings and discussions have been held here around many historical moments, including the American Revolution and the Women’s Suffrage Movement. Faneuil Hall has also been a stage for many political figures to speak, including Susan B. Anthony, John F. Kennedy, and Barack Obama. 

Day 2: Two Famous Neighborhoods & A 100-Year-Old Stained Glass Map

Beacon & Newbury Streets are two of the most famous in Boston. Beacon Street is known for mansions that look over the Boston Common, and Newbury Street is famous for its shopping and dining. Eight blocks have everything from designer boutiques to small businesses, including coffee, art, retail, and more. Newbury is a bustling street with outdoor cafes and lots of life. Another location of The Thinking Cup is here, and it has a quiet and comfortable ambiance that is ideal for starting the day slowly.

Boylston Street is home to Copley Square, Trinity Church, the Boston Public Library, and many great restaurants and shops. Trinity Church was named one of the top ten buildings in the country by the American Association of Architects and has a 150-year history. Don’t miss Tatte’s Bakery, a local and tourist favorite, and head towards Massachusetts Ave, where you can visit the Mapparium at Mary Baker Eddy Library. The Mapparium is one of the most unique interactive historical experiences. A three-story stained-glass globe shows a map of the planet from 1935. Enjoy a rare look at the world before World War II up close and personal. 

Commonwealth Avenue is another famous street in Boston, with a “greenway” in the center featuring memorials and statues such as the Boston Women’s Memorial and a statue of Alexander Hamilton. Despite being in the center of a busy road, it’s a beautiful, surprisingly peaceful path, with benches scattered throughout. Brownstones line either side of Commonwealth Avenue and are pretty photogenic if you enjoy snapping photos of architecture. 

Still have time left? Venture over to the Boston Common and Beacon Hill. The Boston Common borders the Beacon Hill, Back Bay, and Downtown neighborhoods with a 50-acre park, frog pond, ball fields, and plenty of greenery. Wander down the many different paths, soak up the sun surrounded by magnificent trees, and find an old bench to sit and read. The oldest public park, the Boston Common, was established in 1634 and has a colorful history. What started as “common land” for colonists to set livestock grazing, it has been the site where Puritans carried out punishments, an execution site of witches, pirates, and criminals, a camp for the British military during the Revolutionary era, where rallies and gatherings of all shape took place, and so much more. 

Beacon Hill is one of our favorite neighborhoods in Boston, and it has a charming, historic atmosphere. Home to the famous Acorn Street (considered the most photographed street in the US), Beacon Hill is exactly what comes to mind when picturing Boston. This is a primarily residential neighborhood with old-fashioned street lamps, cobblestone streets, and even more historic buildings, but wandering through it is worth the climb. Speaking of climbs, Beacon Hill has the highest point in the city – thus, the name – and is home to several landmarks, including the Massachusetts State House, Boston African American National Historic Site, Museum of African American History, Rose Nichols House Museum, and more. 

Back-Up Day: John F. Kennedy Presidential Library & Museum

Should inclement weather keep you from wandering outdoors during your trip, the John F. Kennedy Presidential Library and Museum will fill a rainy afternoon. It hardly seems fair to list this excellent spot as a “backup,” but considering it’s a little off the beaten path from the main downtown area, it’s best to fit this in when you have more time to visit – or a rainy day to fill! 

Dedicated to the memory of JFK, the library has breathtaking views of the city’s waterfront which should earn a spot in any itinerary. Upon arrival, the experience begins with a short film documenting the life of JFK up to his first election for the presidency. The exhibits feature an in-depth look at his inaugural presidential campaign and ultimate election. Guests learn about his life with Jacqueline Kennedy Onassis and their kids and what life was like inside the White House. Exhibits dive into significant moments throughout his presidency, including the Cuban Missile Crisis, the establishment of the Peace Corps, and the space program. 

Other exhibits are centered around Robert Kennedy, highlighting his time as Attorney General, and a few focused on Jackie Kennedy. They have a collection of her designer dresses worn for special events and a detailed section documenting her work as First Lady, such as advocating for the arts and preserving history. Two special exhibits outside the Kennedy family include the Freedom 7 Space Capsule and the Ernest Hemingway Collection. The museum has short films throughout the exhibits that dive deeper into significant historical events - perfect if you need to fill a long afternoon indoors.