3 Day Boston Itinerary (Planned By a Local With Map)

👉 Jump to: Day 1 | Day 2 | Day 3 | Where to Stay | Map | Getting Around | Tips | FAQ | Get Printable Version

Need help planning for Boston? Just follow this itinerary, which is perfectly planned for maximizing your time in the city. 

I’m a Boston local who loves exploring the city by planning exciting weekend activities with my daughter and sharing these places with loved ones. Boston has a wealth of history and culture. From historic sites to museums, top-tourist attractions, dining, and entertainment, you will find that there are so many exciting things to do here.

I’ve created this carefully planned 3-day itinerary to help you enjoy the best of Boston. It includes top attractions, options for different visitors, hotel recommendations, and so much more. 

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3 Day Boston Itinerary

To plan the perfect itinerary, you first need the perfect hotel.

If these hotels still have availability for your dates, they are my top recommendations:

• 🏆 Best Overall Hotel – Four Seasons Hotel One Dalton Street
• 🗺️ Best Location – Courtyard Boston Downtown/North Station
• 💎 Best Luxury – ​​XV Beacon
• 🛏️ Best Budget Option – The Revolution Hotel
• 🏠 Apartments – Find a Rental in Boston

Accommodation sorted? Let’s get planning your Boston adventure:

🖨️ Get a free, printable version of this itinerary!

Day 1 – Get to Know Boston’s History

Morning

At the start of your first day in Boston, head to the Prudential Center in Back Bay. Shoot up to the 52nd floor to experience The View Boston. This observation deck offers 360-degree views of the entire city and interactive exhibits to learn more about its history. Doors open at 10 am. 

Before leaving the Prudential Center, make a pit stop at Eataly. I love this Italian market. They offer high-quality products from Italy. Grab an espresso and a fresh panini to get your day going. 

When you are done with your morning breakfast, exit on Boylston Street and stroll over to Copley Square. Take in the views of Trinity Church before popping into the Boston Public Library. This library has a wealth of history, art, and culture. The marble stairs lead up to the second floor where you can snap pictures of the Instagramable Bates Reading Room. 

Just a block away is the iconic Newbury Street for shopping. Stroll through popular stores such as Zara, Suitsupply, Sephora, Restoration Hardware, Valentino, and many more. 

By this time, you will be hungry. There are an abundance of restaurants along Newbury Street. I suggest you grab lunch at Contessa. This rooftop restaurant offers more incredible city views. Just note that a reservation is required a few weeks in advance. Otherwise, you may not get a table. 

Afternoon

Walk your lunch off with an afternoon stroll through the Boston Public Garden. This botanical garden was made for scenic walks with weeping willows, tulips, roses, and its iconic swan boat ride in the lagoon. 

Head to the adjacent Boston Common next, the oldest public park in the nation. This marks the start of the Freedom Trail. The 2.5-mile trail covers the story of the Revolutionary War and takes about 90 minutes to complete. 

I suggest you do a self guided tour of the Freedom Trail. With the flexibility, you will have more time to explore the sites and neighborhoods. 

Follow the red brick trail through Downtown Boston and see iconic buildings such as the Old State House, Faneuil Hall Marketplace, and Quincy Market. 

Cross through the Rose Kennedy Greenway. This urban park has open lawns and amazing waterfront views. 

This will lead you into the North End neighborhood. Along the trail, you will pass by the Paul Revere House and the Old North Church. 

If you need a late afternoon pick-me-up, there are plenty of Italian coffee shops and pastries to choose from. I recommend a cappuccino and biscotti from Caffe Vittoria. This coffee shop is cash only. 

Evening 

By the evening, you will be wrapping up the Freedom Trail in Charlestown. Explore the USS Constitution with a free museum and tour of the old warship. Just be aware that the museum closes at 5 pm daily. 

The Bunker Hill Monument is the final stop of the Freedom Trail. This monument commemorates the battle that took place against the British in 1775. 

Finally, treat yourself to a nice dinner. Just steps away from the Bunker Hill Monument is Waverly Kitchen and Bar. They offer satisfying meals with great views and remarkable decor. Walk-ins are always welcome. 

Day 2 – Explore Museums or Go Watch the Red Sox

Morning 

For breakfast or brunch, head to Tatte Bakery and Cafe. This coffee spot is a local Boston favorite and there are 22 locations all over the city. 

Depending on which afternoon and evening option you choose, you could either head to the Fenway location on Boylston St, or the North Eastern Campus on Huntington Ave. 

The Parisian-style cafe offers baked goods and warm drinks with an Israeli twist. Make sure to order their house latte. It’s sweetened with honey and cardamom. 

Afternoon & Evening Option 1: Explore Museums

Boston is a city that is celebrated for its arts & culture. If you are an art lover, you’re in for a treat. Day 2 will be spent wandering through either the Museum of Fine Arts Boston or the Isabella Stewart Gardner Museum, two of Boston’s best museums.

The Museum of Fine Arts is a world-renowned museum that features over 100 galleries of paintings, sculptures, artifacts, instruments, and more. Grab a light meal at New American Cafe located in their courtyard if you get hungry.

The Isabella Stewart Gardner Museum features a stunning Venetian-style courtyard. It houses the private collection of the American art patron, Isabella Stewart Gardner. She collected pieces of art, tapestries, and paintings from different eras and cultures. Grab something to nibble on at Cafe G in their modern wing. 

After an afternoon of strolling through the museum of your choice, head out for dinner. Make a reservation at Blue Ribbon Brasserie inside Hotel Commonwealth. This is a restaurant the whole family can enjoy. 

Afternoon & Evening Option 2: Go Watch the Red Sox

Boston has a reputation for being home to some of the most die-hard sports fans. Head to Fenway Park, home to Boston’s most cherished sports team, the Red Sox.

Sports lovers will soak in the larger-than-life energy experienced at the nation’s oldest ballpark. If you are in town during baseball season, a Boston Red Sox game is the most iconic experience in the city. Check their schedule and tickets before your trip. 

Take a tour of the historic Fenway Park if you are in town when the Sox aren’t playing. The guided tour will go over the 100+ history of the ballpark stadium and the famous Red Sox. 

Before or after a game, wander around for food and drinks. There are so many options to choose from within blocks of the stadium. 

Need help choosing a place to eat? Hojoko is an upbeat Japanese Tavern inside the Verb Hotel. Citizen Public House & Oyster has a great raw bar and craft cocktails. Can’t decide? Try Time Out Market which offers 15 different dining and drinking sites.

Day 3 – Go Across the Charles River to Harvard University

Morning

Start your morning across the Charles River at Black Sheep Bagel Cafe in Cambridge. This cozy spot offers a variety of bagels, sandwiches, and coffee. Order the Cafe con Leche, you won’t be disappointed.

After your morning breakfast, take a walk around Harvard Square. It is the historic center of Cambridge and is filled with many more little shops, cafes, and restaurants. 

Make your way up John F. Kennedy Street to reach the Harvard University Campus. It is open to the public. Make sure to book a walking tour of Harvard’s campus in advance. 

This free tour is guided by Harvard students. You will get to see the historic Harvard Hall and the iconic Harvard Yard. Make sure you stop at the Harvard Book Store after your tour for some Harvard University swagger. 

Afternoon

In the afternoon head to Henrietta’s Table for a late brunch. It is a chic restaurant offering fresh farm-style dishes. 

After your late brunch, head to a museum. Harvard University is home to the Harvard Art Museum and the Harvard Museum of Natural History. 

The Harvard Art Museum is Harvard’s oldest museum. The small museum is free to the public and houses European and American art. There is a small cafeteria on the first floor if you need to grab a bite to eat. 

The Harvard Museum of Natural History combines historic exhibits with innovative new ones. Their collection includes natural science artifacts such as animals and minerals. Check out their famous Glass Flowers exhibit. 

Evening 

In the evening, after the museum, grab dinner at La Fabrica Central. This lively restaurant serves Spanish Caribbean dishes with live music and requires a reservation in advance. The salsa band is incredible to listen to and dance to. Their mofongo dish is a must paired with one of their signature mojitos. 

If dancing isn’t your thing, catch a movie at Brattle Theater. This small movie house features indie and classical films. This little gem has a lot of movie history with a schedule that is always changing. Check their website to see what’s playing. 

Where to Stay in Boston

Best Hotels 

Boston has a vibrant hotel scene. There is a mix of historic and boutique options to choose from. If you need more information, check out our guide on where to stay in Boston. 

• Budget – Hotel Veritas
• Mid-Range – The Verb Hotel
• Luxury – The Newbury Boston
• For Families – Boston Marriott Copley Place

Best Neighborhoods & Areas

Boston is a city that is rich in history, culture, and attractions. There are so many areas to explore and each area has its personality. Look at our guide on the best neighborhoods in Boston for more information. 

• Back Bay (Search apartments in Back Bay) – This popular neighborhood is known for its shopping and dining. There are a lot of historic and cultural attractions in this area. 
• North End (Search apartments in North End) – This historic neighborhood is known for its Italian community. This waterfront area is filled with historic buildings, such as Old North Church.  
• Downtown (Search apartments in Downtown) – This vibrant neighborhood is the heart of Boston. It offers big-city fun but on a much smaller scale. Downtown is a hub for shopping, dining, theater, and art. 
• Fenway/Kenmore Square (Search apartments in Fenway/Kenmore) – This neighborhood is home to the iconic Fenway Park. It offers a lively environment with plenty of entertainment and culture. 

A Complete Map of this Itinerary

Here is a Google Map with all the stops, attractions, and hotels mentioned in this post.

How to Get Around in Boston

Boston is a city that can easily be navigated by foot. It’s a compact city that has accessible public transportation, too. The T (MBTA) gives you access to major Boston neighborhoods and areas. A reloadable CharlieCard can be purchased at all train stops. Taking an Uber or Lyft is also a common way to get around the city.

A car is not necessarily needed to get around. You can always rent a car if you are planning to explore other areas outside of Boston.

Itinerary Planning Tips

Tip #1 – Be Prepared for Lots of Walking

There is a lot of walking to be done in Boston. It is one of the most pedestrian-friendly cities in the country. Be sure to pack comfortable walking shoes. These everyday sneakers provide comfort all day long and the classic style goes with any outfit you pack. 

For more information on what to pack, read our Boston Packing Checklist.

Tip #2 – Carry a Day Bag

Bring a day bag with you. A tote bag or backpack is great for making sure you have everything you need for a day in Boston. This travel backpack has durable material with lots of pockets to keep all of your items organized. Bringing a day bag will also help you save money in Boston, as the city charges bag fees.

📚 Related Reading: Safety in Boston 

Tip #3 – Reserve in Advance

Boston restaurants get booked up quickly. I recommend going online to book your reservations in advance. Some restaurants may require you to reserve a table a few weeks before your trip. Plan accordingly. 

Tip #4 – Pack a Water Bottle

Pack a reusable water bottle that can easily be refilled. It is important to stay hydrated as you explore the city, especially if you come in the summer, which is one of the best times to visit Boston. This insulated filtered water bottle keeps your water tasting fresh with a Brita filter. 

FAQs

How many days is enough? 

3 to 5 days should be enough to experience Boston. Three days is usually enough time to see most top attractions and explore different neighborhoods of the city. If it is your first time in Boston, I would suggest at least 4 days to visit. 

Is Boston worth a trip?

Boston is worth a trip! It is the most visited city in all of Massachusetts. It is rich in history and culture. From historic sites, museums, entertainment, shopping, dining, and more—you are bound to have fun during your trip. 

What should I pack for a 3-day trip?

Pack comfortable walking shoes for your trip to Boston. This city was made for walking. Make sure you have comfortable clothing in your suitcase for exploring the city. The key is to bring layers you can easily put on or take off as needed. For more, see my Boston packing list.

🖨️ Don’t forget! You can get a free, printable version of this itinerary here!

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Whether you are shopping on Newbury Street in Back Bay or singing “Sweet Caroline” at a Red Sox game, you are bound to make lasting memories in Boston.

For more planning fun, check out my 19 Favorite Day Trips from Boston.

(Featured Image Credit: f11photo / Shutterstock.com)