Boston Itinerary A Weekend Trip to Boston, MA by JetSettingFools.com

Boston Itinerary: A Weekend Trip To Boston, MA

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A weekend trip to Boston is a fabulous quick getaway – and we designed the perfect Boston itinerary for travelers who want to see the best of the city! Packed with iconic sights, fascinating history and local cuisine, a weekend in Boston is an ideal trip for people who love to experience diverse and exciting places.

 

Weekend Trip To Boston, Massachusetts

On a Boston weekend trip, visitors have an array of options regarding how to spend their time. In our Boston Itinerary, we feature a range of activities so that visitors can get a taste of all the city has to offer. We highlight top Boston attractions and intriguing neighborhoods – as well as historic places and iconic Boston eateries. Our detailed itinerary for a Boston getaway weekend is all you need to plan your trip!

 

3 Days In Boston

In our plan for a weekend getaway to Boston, we outline the best way to see Boston in 3 days. Our Boston 3-Day Itinerary assumes that you will spend a long weekend in Boston, arriving on Friday/Saturday afternoon and staying until Sunday/Monday evening.

However, because we know not all Boston vacations take place over the weekend, our trip plan can be used for weekday visits as well.

Furthermore, we understand that not everyone is planning 3 days for Boston weekends. Some travelers are limited to visiting Boston in a day, while others are trying to plan a 5-Day Boston getaway. To help fellow travelers plan their perfect Boston trip, at the end of the post we outline several sample Boston itineraries so that you can plan your perfect trip.

Want more tips for quick trips? Get inspired with the 20 Best Weekend Getaways in the US!

Our guide to the Best Weekend Getaways in USA Top 20 Destinations

Best Weekend Getaways in USA Top 20 Destinations

 

Weekend In Boston Itinerary

When we visited a friend for a long weekend in Boston it wasn’t our first trip to the city. Our previous trips, however, revolved around beer and baseball (admittedly, two of the best things about Boston!), but we had missed out on a lot that the city has to offer.

On this trip, we again showed up with no plans. Our friend, however, was armed with an entire binder of information that included a detailed plan for our three days in Boston. Her Boston 3-Day Itinerary included sights and attractions we had missed on previous trips – and we were ecstatic to finally have a local showing us the best of Boston. As a perfect introduction to the city, we are sharing the details of her organized weekend Boston trip plan.

Our trip plan includes absolutely everything you need to know for visiting Boston in 3 days! In addition to our day-by-day Boston guide, we include tips for how to get there, where to stay and what to pack.

Save, Pin or Bookmark this Boston travel blog post so that you can use it as you plan – and during – your trip to Boston!

 

Day 1: Going Out In Boston – Restaurants, Bars and Beer

After getting situated in your accommodations (suggestions below!), start your Boston trip itinerary off right – and head out for a fun night on the town!

Weekend in Boston Itinerary by JetSettingFools.com

 

Boston Brewery Tour

Boston has a long and interesting history with beer and taverns that date to the city’s founding in the mid-1600s – so, when you plan a trip to Boston, you should try the local brew. In addition to the historic brewpubs that still stand in the city (we get to those on Day 2!), there are an incredible number of modern local breweries where you can get a taste of the city as well. 

A brewery tour in Boston in a fantastic way to kick off your Weekend in Boston Itinerary! It is fairly easy to plan your own bar-hopping taproom route, but joining an organized tour is likely a lot more fun! An evening beer tour – like this one! – includes plenty of samples!

 

Seaport District Restaurants

Seaport – or the South Boston Waterfront – is a recently revitalized area in the city. Appealing to tech and innovation companies, the hip waterfront district is a mixed-use Live, Work, Play neighborhood. Seaport is home to about 80 restaurants, making it one of the top dining destinations in the city.

On a weekend in Boston, eating seafood is a must – and there is no better place to get your fill of lobster rolls, crab claws and oyster shooters than Seaport! Home to numerous Boston seafood restaurants, we recommend eating at one of the city’s highly rated restaurants, like The Barking Crab or Legal Harborside.

For after-dinner drinks, head up to the swanky Lookout Rooftop and Bar. Or, for something a little more down to earth, check out the Harpoon Brewery and Beer Hall.

 

Day 2: Freedom Trail, Famous Landmarks and Fenway Park

Day 2 of your Boston Weekend Itinerary is all about historic spots, markets, parks and the Red Sox! Learn about the city’s enthralling history, visit top Boston sights and take in a baseball game at the famous Fenway Park.

Boston Itinerary Plan for a perfect Boston Weekend by JetSettingFools.com

 

Freedom Trail Boston

Walking the 2.5-mile Freedom Trail is a must-do activity on weekend trips to Boston! The full route includes 16 of the city’s most historic sites that played a direct role in shaping the future of America. The trail is easy to follow – as it is marked by a red stripe through the city streets and all 16 destinations are marked with informational plaques.

Visitors can embark on an engaging guided tour – like this one! – where a local guide will provide facts about the history of Boston.

There are many benefits to taking a tour, but the walk can also be done without a guide. Guests exploring on their own will be able to enter sites along the way and make a few detours to other nearby Boston points of interest. The amount of time it will take to complete the trail will depend on curiosity and pace, so we recommend getting an early start and finishing the trail by mid-afternoon.

Pro Tip: Use this map for trip planning the Boston Freedom Trail – but we recommend walking the route in reverse! Start in the north at the USS Constitution and Bunker Hill, then walk south on the Freedom Trail to Boston Common (from which we continue our exploration of Boston in Back Bay!).

 

Lunch on the Freedom Trail

There are plenty of places to stop to eat along the Freedom Trail, however we have two recommendations for where to eat lunch on Day 2 of your Boston 3 Day Itinerary. 

Faneuil Hall is an official stop on the historical Freedom Trail and is part of  complex of buildings called the Faneuil Hall Marketplace (which also includes the Quincy Market). The historic market dates to the mid-1800s and today is packed with Boston’s most famous eateries.

On the other hand, you could consider eating at a historical pub, The Bell in Hand Tavern (near Faneuil Hall), which is not part of the Freedom Trail, but claims to be the oldest tavern in America. 

 

Boston Common and Boston Public Garden

Anyone visiting Boston in a weekend will want to spend some time in Boston Common. The park was established in 1634, making it the oldest park in the USA. Stroll through the park from east to west, passing by the popular Frog Pond and into Boston Public Garden. 

The Boston Public Garden is a botanical garden (the first in America) and was opened to the public in 1838. The two most popular sights at the garden are the Swan Boats and the Make Way for Ducklings statue. It is highly recommended that you include paddling a Swan Boat to your Boston trip planner!

 

Back Bay Boston

Built on reclaimed land along the marshy banks of the Charles River, the affluent Back Bay neighborhood features wide, tree-lined boulevards and historic Victorian Brownstones. However, Back Bay also thrives as a commercial hub and one of the top shopping destinations in Boston. The district is a must-see when you visit Boston for the weekend.

At the heart of the district is Copley Square, which is where the famed Boston Public Library stands. Other significant Back Bay structures include 200 Clarendon Street (formerly John Hancock Tower, which still ranks the tallest building in New England), the Trinity Church and the Prudential Tower.

Pro Tip: Get an overview of the Freedom Trail and Back Bay on a 2-hour guided tour of the area. The tour covers some ground and is highlighted by an entertaining recount of Boston’s history.

 

Red Sox Game at Fenway Park

This wouldn’t be the Best Boston Itinerary if we didn’t include watching the Red Sox! End the second day of your Weekend in Boston Itinerary watching a baseball game at the famous Fenway Park – one of the greatest sports venues in the world. Built in 1912, Fenway reigns as the oldest MLB ballpark – and it’s also one of the smallest (so be sure to buy tickets in advance!).

Pro Tip: If the Red Sox are playing away or you are visiting Boston outside of the baseball season, you can still get a glimpse of the ballpark from the iconic Bleacher Bar. Occupying the former visiting team batting cages, The Bleacher Bar is situated beneath the Fenway bleachers with a window that provides a view of the outfield.

 

Day 3: Harvard, Districts and Duck Boat Tour

On the last day of your 3 Days in Boston Itinerary, visit one of the most prestigious campuses in the world, explore more neighborhoods and end your time in Boston on an oddly popular Duck Boat Tour.

Boston Weekend Itinerary by JetSettingFools.com

 

Harvard

Impressive and classic, the Ivy League Harvard campus is just a short jaunt from Boston (and easy to reach using public transport) – so it is easy to include in your 3 Day Boston Itinerary. Visitors can wander the campus to top sights, like Harvard Yard, then head to the Mr. Bartley’s Burgers, an institution since 1960 that serves up wickedly good burgers.

Pro Tip: Discover Harvard sights on your own – or join an informative student-guided tour to all the hotspots!

 

Beacon Hill or Southie Boston

When you are tasked with deciding what to do in Boston for a weekend, neighborhood exploration should definitely be on the list. However, you will need to determine which neighborhoods to see (because the city is too big to see them all in just three days!). 

Beacon Hill

Perhaps the most picturesque neighborhood in Boston, Beacon Hill (located on the north side of Boston Common) is home to the landmark sights and quaint lanes. Visit the golden domed Massachusetts State House, picture-perfect Acorn Street and the well-to-do Louisburg Square. The original Cheers bar, which provided inspiration for the 1980s sitcom of the same name, is located in Beacon Hill…and is a perfect spot for lunch and a brew.

South Boston

Alternatively, delve into South Boston. Southie, a once rough and tumble neighborhood made famous in movies like Good Will Hunting and The Departed, has now seen much gentrification. The area has transformed from a gritty neighborhood into another one of Boston’s hip places to live, eat and play.

The revitalized district – now re-branded as SoBo – still has a few old school haunts, but it is quickly becoming known for its upscale bars and gourmet eateries. Some of the places to visit in Southie include the Lawn on D, Foodie’s Markets and a section of the Harborwalk – a 40-mile coastline walk, which connects South Boston to Pleasure Bay and Castle Island.

 

Duck Boat Tour Boston

After spending the better part of three days in Boston on your feet, it’s time to wrap up your fun weekend in Boston – so sit back, relax and enjoy the ride…on a Duck Boat Tour! Although they seem touristy and corny, a Boston weekend trip would not be complete without taking the Duck Boat Tour.

The famed Boston Duck Boat Tours use replica World War II amphibious road-and-waterway DUKW vehicles to take tourists for a spin around the city streets and on the river. The narrated tours offer a unique vantage point to some of Boston’s top landmarks from the streets and the Charles River. It’s the perfect final activity for your Boston Itinerary!

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More Things To Do In Boston, Massachusetts

We highlighted some of the best activities in our Boston Weekend Itinerary, but fellow travelers planning a trip to Boston may want to include alternate attractions into their trip plan. To help, we are identifying some of the top sights – like museums and day trips – that we left out of our 3-day trip to Boston.

 

Boston Museums

Learn about the city’s history or appreciate fine art at the best museums in Boston!

Boston Tea Party Ships and Museum

Follow the story of the Boston Tea Party, which was a pivotal event in America’s history, through engaging exhibits, historic artifacts and interactive displays. Buy tickets now!

Museum of Fine Arts Boston

The Boston Museum of Fine Arts – or MFA – features more than 450,000 works of art – and entertains more than 1 million visitors each year. The museum ranks as one of the largest art museums in the world; the collection of art spans centuries.

Mapparium Museum Boston

A gigantic stained-glass globe, the Mapparium Museum inside the Mary Baker Eddy Library introduces visitors to an intriguing look at the world circa 1935. Renovated for modern times, the 3-story museum now features a light and sound show.

Pro Tip: Travelers interested in visiting museums and other Boston tourist attractions might want to consider purchasing a money-saving Boston City Pass that allows skip the line access to top sights. Buy it here!

 

Day Trips From Boston

We have packed our Boston 3-Days Itinerary to the brim…but there is so much more to see in the region! Travelers more interested in regional exploration – rather than neighborhood discovery – might want to add a highly-rated tour into their Boston Itinerary. While there are numerous short trips from Boston, we are highlighting the best ones!

Martha’s Vineyard

A summer colony for celebrities and the wealthy, Martha’s Vineyard is a beautiful place to see. On a full-day tour from Boston, visitors travel by mini-coach along the coast to Cape Cod, then board a ferry to the island. Once on Martha’s Vineyard, participants can choose to explore on their own or upgrade their experience to a guided tour. Find out more!

Plymouth Colony

Take a day trip from Boston back in time! Visit the Plimoth Plantation – a recreation of the 17th century Plymouth Colony established by Pilgrims, Plymouth Rock – where the English colonists landed, and other historical sites on an all-day tour. Get the details!

Salem, Massachusetts

Well-known for the infamous Salem Witch Trials of 1692, Salem is a historic coastal city that is not too far from Boston. Visitors can make the trip from Boston to Salem on their own using the convenient ferry and can join a walking tour once in Salem.


 

How Many Days Do You Need to Visit Boston?

Boston is a diverse city. It is historic and modern. Shabby and chic. Lively and relaxing. Therefore, determining how many days to spend in Boston can be tricky. We love the city – and could easily spend weeks there, never getting bored. 

That said, to really get a good feel for the city, we think 3 days in Boston is ideal…but 5 days would be even better. 

That is not to say that if you are limited to a Boston One Day Itinerary that you should skip the city and go somewhere else instead. There is so much that you can see and do in limited time…and we will show you how!

Boston Itinerary How To Spend a Weekend in Boston by JetSettingFools.com

Sample Boston Itineraries

We detailed the best 3-Day Itinerary for Boston – but what if you are planning a longer or shorter stay? No worries! We have Boston itinerary suggestions for everything from a 1-Day Boston Itinerary to a Boston Itinerary for 5 days!

 

Boston In 1 Day Itinerary

Planning a 1 Day in Boston Itinerary is quite the task – there is so much to see and do! That said, if one day in Boston is all you have, then we suggest making the most of it!

Boston Itinerary 1 Day

For a One Day Boston Itinerary, we recommend following our outline for Day 2 of our above itinerary. If there is no baseball game during your visit, instead opt to take the brewery tour that we recommend on Day 1.

Pro Tip: Visitors pressed for time can streamline their One Day in Boston Itinerary with a convenient self-guided Boston One Day Tour on the Trolley

 

Boston 2-Day Itinerary

Planning a 2-Day Boston Itinerary allows for a lot more sightseeing in the city! That said, you will still need a succinct plan. 

2 Days in Boston Itinerary

To create the ultimate Boston in 2 Days Itinerary, we recommend simply following Days 2 and 3 of our above outlined itinerary. If time allows, squeeze the brewery tour in after the Duck Boat Tour for a fun way to finish off the trip!

 

Alternative Boston Itinerary 3 Days

While our trip plan for what to see in Boston in 3 days is perfect for us, other travelers may want to see different attractions.

Boston Itinerary 3 Days

Rather than using our outline of three days in Boston, fill your trip itinerary with the attractions that are most interesting to you. For example, use our tips for more Boston things to do (like visiting museums or going on day trips) to create your perfect Boston travel itinerary!

 

Boston 4-Day Itinerary

Planning a 4 Days in Boston itinerary allows visitors more time to see the city and the surroundings!

Boston Itinerary 4 Days

To plan a Boston Itinerary for 4 Days, we recommend using our detailed outline for 3 days in Boston, then – on the last day – add one of the top Boston day trips to your trip plan. Alternatively, if you want to stay in the city and on foot, we recommend delving into a neighborhood that you skipped – or taking a longer stroll on the Harborwalk.

 

Boston 5-Day Itinerary

Spending 5 days in Boston is perfect for visitors who really want to see it all! Planning a trip to Boston for 5 days allows plenty of time to explore districts, taste the fare and discover regional sights, too.

Boston Itinerary 5 Days

To create a 5 days in Boston Itinerary, we recommend using our suggestion for 4 days in Boston, then – on your final day in the city – visit some of the city’s most famous museums.

 

New York – Boston Itinerary

New York City and Boston are in close proximity, which makes the two cities perfect to combine on an East Coast trip. 

If you are planning an itinerary that includes both Boston and New York, use tips from our 1-Week New York Itinerary – or, if you are on a budget, use our tips for how to experience NYC on a Budget.

Furthermore, you can add other East Coast cities to your trip – like Philadelphia and Washington DC.


 

Top Tips For Trips In Boston

Now that you know how to visit Boston in 3 days, we have a few final travel tips and packing hacks for your trip!

 

How To Get To Boston

Boston can be reached by car, bus, boat, train or plane. On our Boston weekend trips, we have always arrived by plane to the Boston Logan International Airport. Start your search for the best airfares to BOS on SkyScanner!

Boston Airport to Downtown Boston

To get from the Boston Logan Airport into the city, visitors can use taxis, Uber, private transport or shared transport. It is also possible to get from the airport to the city via The T public transportation.

 

Where To Stay In Boston For A Weekend Trip

We think the best place to stay in Boston is downtown – or in one of the adjacent, centrally located neighborhoods. On our trips to the city, we have always stayed with friends, but there is a wide range of Boston accommodations – from 4-star hotels to Airbnb apartments.

Generally, we prefer staying in Airbnb apartments when traveling. We have found that we can usually get more space (including a kitchen to make breakfasts!) for less money than hotels. (And you can save even more money when you use this link to create your Airbnb account!)

However, guests who would rather stay in traditional accommodations have plenty of Boston hotels to choose from. Top choices for the best location include Club Quarters (an affordable option in the heart of the city) and Omni Parker House Hotel (a luxury stay that is close to everything!). The citizenM is a hip and modern hotel in the nearby West End.

 

What To Pack For Your Trip To Boston

Packing for a trip can be a chore! We share our general tips for packing on our Ultimate Packing List, but have a few Boston-specific packing tips, too!

 

Weather Appropriate Apparel

The weather in Boston is unpredictable! Summers are typically hot and humid and winters can be cold and wet – and spring and autumn can be anything in between! For your trip to Boston, make sure you pack clothing that is suited for the weather – and packing clothing that can be layered is always a good idea! Regardless of the season, it is smart bring a travel umbrella or packable raincoat. And, in the summertime, sunscreen is a must!

 

City Walking Shoes for Your Weekend in Boston

In our 3-Day Boston Itinerary, we cover some ground! Be sure to pack comfortable city walking shoes for your trip. Flat, rubber-soled shoes – like these Columbia shoes for women that I wear or Merrell trail shoes that Kris likes – are best for the cobblestone lanes and Boston city streets.

 

Travel Camera

As one of the most historic cities in America, Boston is gorgeous – and, if you are anything like us, you will be snapping a ton of pictures during your stay. Rather than attempting to capture the city sights with a cell phone camera, we recommend upgrading to an actual camera. We use a Canon Rebel with an everyday 18-135mm lens that takes great pictures…and it is easy to use! Best of all, the camera comes with a complete kit, which is perfect for beginner photographers!

 

Great Day Bag

Whether you travel with a backpack or a suitcase, you will definitely want a great day pack to organize and secure all your essential, everyday travel items.

 

Travel Insurance

We think travel insurance is a must on any trip – even on a weekend trip to Boston! Trip insurance cover you in the event of cancelled flights and lost luggage – among many other unfortunate situations! Get rates and coverage details at World Nomads.

 

Start planning your trip to Boston! Search for the lowest airfares, the best accommodations and fun things to do…then start packing!  Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page!

 

More USA Destinations: East to West

There is no shortage of places to visit in the United States! Get inspired for your next trip with our list of the Best USA Destinations for a Weekend Trip!

Seeking more East Coast destinations? Find all of our itineraries for the best USA cities – like New York, Washington DC and Philadelphia – on our USA Destinations Page

Are you also venturing out West in the USA? Be sure to read our detailed guides to California, Montana, A Weekend In San Diego, San Francisco Weekend Trip, the Mile High City of Denver, hiking on the Oregon Coast, A Seattle Getaway, chilling in Vancouver WA and an adventure in Flagstaff AZ!

 

We Want To Know: How would you spend 3 days in Boston? Is there anything you would add to our Boston Itinerary? 

 

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A Weekend Trip to Boston Itinerary by JetSettingFools.com

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