2 Day Boston Itinerary: The Best Weekend Trip

Boston is the country’s oldest and most historic city. It’s the perfect balance of small-town charm and big-city hustle. Enjoy a stroll along cobblestone streets. Visit Harvard, the most profound university in the world. Catch a Red Sox game at Fenway. Eat at some of the best Italian restaurants. Boston has a little something for everyone to enjoy! If you’re looking to plan a weekend trip to Boston. This guide outlines a perfect 2 Day in Boston Itinerary to take in the best sights in Boston in only 2-3 days.

Planning Your Trip

Planning a trip to Boston can be overwhelming, but with a little preparation, you can make the most of your visit. Here are some tips to help you plan your trip:

• Best Time to Visit: The best time to visit Boston is during the spring (April-May) and fall (September-November) when the weather is mild and pleasant. These seasons offer the perfect conditions for walking tours and outdoor activities, making your visit to Boston even more enjoyable.
• Getting There: Boston Logan International Airport (BOS) is the closest airport to the city, providing convenient access for travelers flying in. If you prefer ground transportation, you can also take a train or bus to Boston from nearby cities, making it easy to visit Boston from various locations.
• Accommodation: Boston has a wide range of accommodation options, from budget-friendly hostels to luxury hotels. Consider staying in the city center to make the most of your visit. This will put you within walking distance of many attractions, allowing you to maximize your time exploring the city.
• Transportation: Boston has a comprehensive public transportation system, including the subway, known as the “T” in which you can purchase a reloadable Charlie Card, Boston’s equivalent to the metro card, buses, and ferries. You can also walk or bike around the city, as many of the main attractions are within proximity. This makes it easy to navigate and enjoy all that Boston has to offer.

Best Things to Do in Boston

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Walk the Freedom Trail

The Freedom Trail is a 2.5-mile walk through Boston that covers 16 significant places of history that impacted the American Revolution. One of the key stops along the Freedom Trail is the Paul Revere House, the oldest building in downtown Boston. This trail was preserved and dedicated to the city of Boston in 1951, and today over 4 million visitors take this walk annually.

This trail covers Boston Common, King’s Chapel & King’s burying ground, Granary Burying Ground, the Old South Meeting House, the Old State House, the old north church, and many more. You can cover a lot of ground when walking the Freedom Trail and should be experienced by all who visit. If you prefer a guided tour this one is a great option!

Visit Beacon Hill

Notably, the most charming neighborhood in Boston and maybe even the entirety of the United States is Beacon Hill. Beacon Hill is home to The Historic Massachusetts State House, gaslight narrow streets, and picturesque homes lining a cobblestone street. Boston Common lines part of this neighborhood and you can easily spend hours walking around looking at the charming homes and stoops.

For the most popular part of Beacon Hill, make a visit to Acorn Street. Nearby is a delicious cafe called Tatte where you can indulge in pastries and aromatic coffee. Also, make a stop at the most charming bookstore in Boston, Beacon Hill Books & Cafe. Finally, if you’re looking to visit the original Cheers Bar, it’s located in this neighborhood at 84 Beacon St.

Visit Boston Common

The famous public park where the infamous movie “Good Will Hunting” was filmed is called Boston Common. It’s also the oldest public park in the entire United States dating back to 1634. Some refer to this part of the city as the heart of Boston, and I can completely see why. Aside from the fact that back in the day this was a place of public punishments, it’s one of the prettiest parks I’ve been to. Adjacent to the common is the Boston Public Gaden. Both of these parks span across 44 acres in downtown Boston and is the perfect place to spend an afternoon.

Explore the Back Bay Neighborhood

The Back Bay neighborhood spans around Copley Square and is a hip stylish neighborhood filled with the best shopping, art galleries, and patio cafes. A long walk on Newbury Street can take you to lots of trendy places like Saltie Girl and tons of chic shops.

Back Bay also is home to the Boston Public Library and Trinity Church. Out of our entire Boston weekend trip, the library was my favorite part because it reminded me of Hogwarts. Also, the courtyard was an architectural dream. Don’t miss out on those 19th-century pieces of history!

Enjoy an Italian Meal in North End

The North End district is a lively neighborhood that is similar to that of Little Italy in NYC. It’s home to Boston’s oldest residential neighborhoods and spans one square mile on Bostons waterfront. Some of the best Italian food on the east coast can be found here. Finally, if you visit this neighborhood Mike’s Pastry is a right of passage. Their cannolis are delicious and the size of your head. It’s well worth the hour+ wait in line.

Visit Cambridge

Cambridge is a college town known for being home to the most prestigious Ivy League school in the United States, Harvard. But Cambridge is so much more than a college town. It’s located along the Charles River which showcases beautiful views of Boston, has a great foodie scene, and a thriving music and art scene.

You can take a guided tour of Harvard University, stroll through the historic campus, visit the Harvard Museum of Natural History, and soak in the academic atmosphere. You can easily spend an entire afternoon exploring all that Cambridge has to offer.

Explore the Market District

Boston’s Market District dates back to the 1700s and is home to the Boston Public Market, also known as Fanueil Hall. It’s located in downtown Boston, steps away from the waterfront and is home to 70 retailers. It’s best to come here hungry and experience worldwide cuisine, pubs, restaurants, and the world-famous Quincy Market Colonnade. Finally, you can easily post up and watch the street performers and musicians who fill the cobblestone streets.

https://www.viator.com/tours/Boston/Explore-Revolutionary-Boston-Freedom-Trail-History-Tour/d678-66111P3

Eat the Original Boston Creme Pie

The Boston Creme Pie is an iconic culinary creation that dates back to 1856. The Omni Parker House hotel was the original creator and they still serve the timeless recipe today! They have since shared the recipe for you to make at home but if you want a taste of history visit one of the hotel eateries.

Visit the Isabella Stewart Gardner Museum

This famous art museum houses significant examples of European, Asian, and American Art. It is notably known for its stunning courtyard gardens and unfortunately the art heist that took place here in 1990. Sadly, 13 pieces of art were taken during that theft and still to this day remain an unsolved mystery. Nevertheless, a visit to this museum is always a good idea and is one of the prettiest courtyards I have ever seen.

Where to Stay in Boston

1. Mandarin Oriental, Boston: a luxurious stay in the Back Bay, offering elegant rooms, a world-class spa, and easy access to Newbury Street’s high-end shopping and dining. We loved staying near all the best shopping and eateries. Book your stay here!

2. The Langham, Boston: a beautifully restored hotel in the Financial District, blending historic charm with modern luxury. Known for its stunning interiors and exceptional service. Book your stay here!

3. The Newbury Boston: a stylish, boutique hotel located at the entrance of Boston Public Garden. Offers sophisticated rooms, a rooftop restaurant, and an unbeatable location. Book your stay here!

4. The Liberty Hotel: a unique hotel set in a former jail in Beacon Hill, combining historic architecture with a chic, contemporary vibe. It’s close to Charles River Esplanade and great dining spots. Book your stay here!

2 Day Boston Itinerary: Weekend Edition

Friday

• Either drive into Boston or fly into Logan International airport
• 2 pm check into your hotel
• Walk the Freedom Trail
• Walk around Boston Common and enjoy the scenery
• Have an early dinner and catch a baseball game at Fenway Park

Saturday

• Start your day in Cambridge to visit Harvard Square and have brunch
• Visit the Back Bay neighborhood to do some shopping and have lunch
• Explore the Boston Public Library + Trinity Church
• For dinner, have a nice Italian meal in North End
• Visit Mike’s Pastry Shop for a late-night snack

Sunday

• Grab brunch in Beacon Hill and explore one of the cutest neighborhoods in Boston
• Visit the Isabelle Stewart Gardner Museum or the New England Aquarium
• Have lunch at Faneuil Hall Marketplace and watch the street performers perform
• Walk over to the waterfront and check out the Boston Tea Party ships

Alternative Itinerary Ideas

If you have more time in Boston or want to explore different aspects of the city, here are some alternative itinerary ideas:

• Salem, Massachusetts: Located only 40 minutes away from the city is the infamous town of Salem. Known for the witch trials back in the 1600, the lore of this town runs deep and is a must visit for lovers of all things spooky, Hocus Pocus, and witches. Stay tuned for a full blog post outlining the best things to do!
• Museum of Fine Arts: Spend a day exploring the Museum of Fine Arts, one of the largest and most visited art museums in the country. With an extensive collection of artworks from around the world, this museum is a must-visit for art enthusiasts.
• Boston Harbor Islands: Take a ferry to the Boston Harbor Islands, a group of islands with beautiful beaches, hiking trails, and historic sites. Enjoy a day of outdoor adventure, whether it’s hiking, picnicking, or simply relaxing by the water.
• North End Food Tour: Take a food tour of the North End, Boston’s oldest neighborhood, and sample some of the city’s best Italian cuisine. From fresh pasta to delectable pastries, this tour will satisfy your taste buds and give you a deeper appreciation for Boston’s culinary scene.

Final Thoughts

Boston is a city with a rich history, vibrant culture, and stunning architecture. With this itinerary, you’ll get to experience the best of Boston in just 2 days. From the Freedom Trail to the Boston Public Garden, and from the North End to the Back Bay, you’ll see the city’s most iconic landmarks and neighborhoods.

Don’t forget to try some of the city’s famous seafood, Italian food, and Boston cream pie! With a little planning and preparation, you’ll be ready to take on the city and make the most of your visit. Whether you’re walking the historic streets, enjoying a meal in a cozy Italian restaurant, or exploring the beautiful parks, Boston has something special for every traveler!

Thank you for reading my “Complete Weekend Trip to Boston Itinerary”. What are some of your favorite Boston spots to visit? Finally, don’t forget to check out more of my USA Travel Guides.

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XO,

Courtney