Boston Itinerary A Weekend Trip to Boston, MA by

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 with all types of interest!


Weekend Trip to Boston, Massachusetts Itinerary

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.

One of the best things about Boston is that it is fairly compact and walkable – so you can see a lot in a short amount of time. Our weekend in Boston Itinerary is designed to insure you see the top sights and partake in the best activities. 

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

The first question many travelers ask is, How many days in Boston for a trip? In our plan for a weekend getaway to Boston, we outline the best way to see Boston in 3 days. We think visitors can squeeze the top things to do in Boston into a well planned 3 day trip.

Our Boston 3-Day Itinerary assumes that you will spend a long weekend in Boston, arriving early on Friday or Saturday and staying until Sunday or Monday evening. However, as not all Boston vacations take place over the weekend, our trip plan can just as easily be used for weekday visits.

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 with top tips on how to plan a trip to Boston for any timeframe! 


Planning a Weekend in Boston Itinerary

When we recently visited for a long weekend in Boston, it wasn’t our first trip to the city. Our previous Boston weekend trips had revolved around sporting events (admittedly, one of the best things to do in Boston), but we had missed out on a lot of the best Boston sights.

On this weekend Boston trip, we arrived with plans; big plans to see the Best of Boston! We were ready to spend a weekend in Boston that included visiting historic points of interest, exploring Boston neighborhoods and dining on local fare.

Armed with a detailed plan for our three days in Boston (including those sights and attractions we had missed on previous trips) – we were ecstatic to finally have a complete Boston 3-Day Itinerary. Now ,we are sharing those details to help you create your perfect weekend Boston trip plan!

Pro Tip: Get (and stay) organized for your Boston Trip by using our Travel Planning Printables!



Massachusetts State House, Boston

Our Boston long weekend 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 to use as you plan – and during – your trip to Boston!


Day 1: Freedom Trail, Famous Landmarks and Fenway Park

Day 1 of your Boston Weekend Itinerary is all about historic spots, local eats, parks and the Red Sox! After getting situated in your accommodations (suggestions below), start your trip by learning about the enthralling history, visiting top Boston sights and taking in a baseball game at famous Fenway Park.

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Freedom Trail Boston

Marker for the Freedom Trail, Boston, MA, USA

Walking the 2.5-mile Freedom Trail is a must-do activity on weekend trips to Boston. The full route includes 16 of Boston’s top historic sites – all of which played a role in shaping the future of the Untied States of America. 


Sights on the Boston Freedom Trail

View of the Obelisk at Bunker Hill, Boston, MA, USA

The Freedom Trail sights are listed in order so that you end in Boston Common and then continue on from there.

Technically, this is considered walking the trail in reverse – but we think that for the sake of a succinct Boston 3 Days Itinerary, it makes more sense to complete the route in reverse rather than from beginning to end. The order of the sights actually doesn’t matter. In fact, you can pick and choose which sights you want to see if you have other ambitions and interests for things to see in Boston in three days. 

Our recommendations, however is to begin your Freedom Trail Walk in Boston at Bunker Hill. 


Bunker Hill – An obelisk monument marking the first battle of the Revolutionary War; visitors can climb up the tower and visit the nearby museum. 


USS Constitution Museum – Nicknamed Old Ironsides, it is the oldest US warship still floating.


Copp’s Hill Burying Ground – Historic cemetery for North End residents.


Old North Church and Paul Revere Statue – Boston’s oldest church, which is most well-known for it’s part in the start of the American Revolution – One if by land, two if by sea.


Paul Revere House – The home where Paul Revere lived in the late 1700s.


Faneuil Hall – The site of America’s first ‘Town Hall Meeting’ and a place where many events of the American Revolution occurred. 


Boston Massacre Site – The site of the clash between residents and Redcoats in March 1770. 


Old State House – The oldest public building in Boston (circa 1713).


Old South Meeting House – The site of countless meetings and speeches that led to the events of the Boston Tea Party; now a museum. 


Old Corner Bookstore – Built in 1718; it ranks as the oldest commercial building in Boston.


Ben Franklin Statue and Boston Latin School – The oldest public school in the United States, established in 1635, which was attended by Benjamin Franklin.


King’s Chapel and Burying Ground – An Anglican church (Boston’s first) dating to 1686.


Granary Burying Ground – Cemetery dating to 1660 where many famous residents – such as John Hancock, Samuel Adams and Paul Revere – are buried.


Park Street Church – Founded in 1809, the steeple rises 217 feet; it was one of the tallest structures in Boston when it was built. 


Massachusetts State House – Gold-domed building housing Massachusetts government since 1798.


Boston Common – The city’s first (and best!) green space.


Freedom Trail Tour or Self-Guided Walk during your Weekend in Boston?

Visit the USS Constitution Museum, Boston, MA, USA

On your long weekend Boston trip, you will need to decide if you want to join a guided walking tour or complete the Freedom Trail on your own. There are pros and cons to both for your Weekend in Boston Itinerary. 


Guided Tour of Boston

An engaging guided tour – like this one – features a local guide who will provide facts about the history of Boston. Best of all, they will lead the way. However, you will be on the guide’s timetable and will likely not have time to go inside some of the sights. 


Boston Self-Guided Walk

Visitors can also opt to do a Self-Guided Freedom Trail Walk. The trail is fairly easy to follow – as it is marked by a red stripe through the streets of Boston. Plus, all 16 Freedom Trail destinations are marked with informational plaques. For more interesting facts along the way, you can download an audio 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. Expect the walk to last at least 2 hours – but it could take longer depending on your curiosity, pace and detours. We recommend getting an early start and finishing the trail by mid-afternoon.

Pro Tip: Again, we recommend walking the route in reverse of the official listing. Start in the north at Bunker Hill and the USS Constitution, then walk south on the Freedom Trail to Boston Common, from which we continue our exploration of Boston in Back Bay. However, if you complete the route in the opposite direction, just make your way back to Boston Common using public transport (just called the T)- either the Green or Orange line will get you there! 


Lunch on the Freedom Trail

There are plenty of places to stop to eat along the Freedom Trail, however we have a few recommendations for where to eat lunch on Day 1 of your Boston 3 Day Itinerary. All of our recommended Boston restaurants for lunch are in the North End neighborhood along the Freedom Trail route. 


Quincy Market

Eating at the Quincy Market, Boston, Mass

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


The Bell in Hand Tavern

Tavern Bell in Hand, Boston, MA, USA

We love the classic pubs in Boston – and The Bell in Hand Tavern is one of the best! Located along the Freedom Trail (but not an official stop), The Bell in Hand Tavern claims to be the oldest tavern in America. 


Lobster Rolls

Must eat Lobster Roll, Boston, MA

If you are looking for a scrumptious seafood lunch, then a Boston ‘Lobstah’ Roll is the way to go! These two restaurants in Boston are well-known for their Lobster Rolls: Neptune Oyster in the North End and Union Oyster House in Downtown Boston.


Boston Public Market 

An upscale, indoor market, Boston Public Market features 30 local vendors, including numerous chic eateries. The market is across the street from The Bell in Hand. 


Boston Common and Boston Public Garden

Walking in Boston Common, MA

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 walk into Boston Public Garden. 

Boston Public Gardens 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!

Pro Tip: If you complete the Freedom Trail in reverse as we suggest (starting in Bunker Hill), then Boston Common is the last stop on your walk.


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. This 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 first 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!).

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If the Red Sox are playing away or you are visiting Boston outside of the baseball season, you can take a Fenway Park Tour of the stadium instead! The engaging tour is a must for baseball fans – Get the details here!

Pro Tip: Interested visitors can catch just 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 and it’s open to the public – even during games.


More Evening Boston Entertainment

Exterior of the TD Garden Arena, Boston, MA, USA

Baseball isn’t the only sport in the city! The Boston Celtics (basketball) and Boston Bruins (ice hockey) teams play in the city center TD Garden Arena. NFL football team New England Patriots play in nearby Foxborough at Gillette Stadium. 

Not a sports fan? No problem! Instead of including a sporting event in your Boston Weekend Itinerary, spend an evening in the bustling downtown Boston Theater District watching a theatrical performance or comedy show. 


Day 2: Harvard, Districts and Boston Beer

On the second day of your 3 Days in Boston Itinerary, visit one of the most prestigious campuses in the world, explore iconic neighborhoods and end the day on an brewery tour.

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Impressive and classic, the Ivy League Harvard campus is just a short jaunt from Boston (and simple 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 wicked good burgers.

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


Beacon Hill

Historic Acorn St, Beacon Hill, Boston

When deciding what to do in Boston for a weekend, we highly recommend adding Beacon Hill to your list! Perhaps the most picturesque neighborhood in Boston, Beacon Hill (located on the north side of Boston Common) is home to 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.

Pro Tip: Visitors to the Beacon Hill neighborhood can also embark on the 1.5-mile Black Heritage Trail. The 10-sight trail features houses and buildings that celebrate the history of the Black community and the events that took place during the American Civil War. Follow the signs or get more information (and an audio tour!) on the National Park Service website


South Boston

American Flags in Southie, Boston, SoBo, MA, USA

Next up on your Boston visit is Southie. The once rough and tumble neighborhood, made famous in movies like Good Will Hunting and The Departed, has seen a flurry of gentrification in recent years. The area has transformed from a gritty district into another one of Boston’s hip places to live, eat and play.

Now re-branded as SoBo – it 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 the Harborwalk – a 40-mile coastline walk, which connects South Boston to Pleasure Bay and Castle Island.

The Beach at Pleasure Bay, Boston, MA, USA

Pro Tip: Summertime visitors might consider heading to one of the South Boston beaches. Carson Beach and Pleasure Beach are our two top picks for sunbathing – but any stretch of the shoreline is fun to explore!


Boston Brewery Tour

Boston has a long and interesting history with beer – so when you plan a trip to Boston, hoisting a few pints should be on your list! 

The classic taverns and historic brewpubs – some of which date to the city’s founding in the mid-1600s – are excellent places to socialize. There are also an incredible number of Boston craft breweries where you can take a tour and get a taste as well. 

You can create your own brewery tour for your Weekend in Boston Itinerary, as it is fairly easy to plan your own craft taproom route. You can use this list of breweries for tips on where to go.

Pro Tip: However, joining an organized Boston brewery tour is likely a lot more fun! An evening beer tour – like this one – includes samples, transportation and dinner.


Day 3: Boston on the Water

On the final day of your Boston trip itinerary, explore the New England Aquarium, get a taste of clam chowder, head out on the water and then eat a divine seafood meal on the Boston waterfront. 

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New England Aquarium

A must-see in Boston in 3 days, the New England Aquarium is a top attraction – and should definitely be on a Boston family vacation itinerary! 

Located on Central Wharf, the aquarium is a 4-level facility that features a massive fish tank and a variety of sea life. Top attractions are the penguins, seals and the you-can-touch tidepools. 

Pro Tip: Tickets can be purchased at the aquarium or visitors can use the Boston CityPass for entry – which is also valid for harbor cruises, the Museum of Science and other Boston tourist attractions. 


Lunch of Clam Chowder at Boston Sail Loft

Sail Loft Boston Clam Chowder

There are countless restaurants to get a good bowl of chowda in Boston, but far and away our favorite place is Boston Sail Loft. Perched over the water, the relaxing restaurant serves up a delectable and creamy clam chowder. 

Other dishes that we love at Sail Loft are the lobster roll – which is piled high with huge pieces of tasty lobster – and the absolutely decident potato skins!

Pro Tip: If the weather is nice, try to get a seat outside on the small deck! 


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 might seem silly, 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 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!

Pro Tip: If the Duck Boat just isn’t your style, instead consider taking one of the fun Boston Harbor cruises, like the historic Boston Harbor Cruise (get the details!) or join the ever-popular Whale Watching Tour (reserve your seat!).


Seaport District Restaurants

Seaport – or the South Boston Waterfront – is another recently revitalized area. 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 Boston.

On a weekend in Boston, eating seafood is a must – and it would be difficult to find a 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.

Pro Tip: Going out in Boston Seaport isn’t only about eating. 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.


More Things To Do in Boston, Massachusetts

View of North Bank Bridge, Boston, MA, USA

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! You can easily add one of these fascinating museums to your 3 Days in Boston Itinerary by swapping out some of the district exploration or the Duck Boat Tour. 


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.


Isabella Stewart Gardner Museum

From the late 1800s through the early 1900s, Isabelle Stewart Gardner amassed an impressive collection of art works – including masterpiece paintings, tapestries and rare books. The world-class art exhibits are displayed in her beautifully designed, Venetian-inspired mansion. 


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.


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 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!


Boston Tours to 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 Trip from Boston

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 town 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.

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How Many Days Do You Need to Visit Boston?

Old and New in downtown, Boston, MA, USA

Boston is diverse, 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 it, we think 3 days in Boston is ideal…but 5 days would be even better. 

That’s not to say if you are limited to a Boston One Day Itinerary you should skip it and go somewhere else instead. Even limited time…we will show you how to visit Boston!


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 1 of our above itinerary. If there is no sporting event during your visit, instead opt to take the brewery tour that we recommend on Day 2 (or a Boston Food Tour).

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 extremely popular Boston Trolley


Boston 2-Day Itinerary

Planning a 2-Day Boston Itinerary allows for a lot more sightseeing! 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 1 and 2 of our above outlined itinerary. With this trip plan, you can get a really good feel for the city. If time allows, squeeze the duck boat tour after exploring Southie for a fun way to finish off the trip!

However, if you are planning what to do in Boston for 2 days for a family trip, then we recommend using our outlined Days 1 and 3 from above. The aquarium and boat trip will likely be more interesting to kids than neighborhood discovery. 


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. We have made it simple to swap out some of the attractions on our recommended itinerary by offering tips in our section of More Boston Things To Do (like visiting museums or going on day trips). Use these ideas to create your perfect Boston travel itinerary!

For example, art lovers could use our described outline for two days in Boston, then on Day 3, swap out the aquarium for the unique Isabelle Stewart Gardner Museum. 


Boston 4-Day Itinerary

Planning a 4 Days in Boston itinerary allows visitors more time to see sights and the surroundings – and we have tips and fun Boston vacation ideas to show you how!


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

There are still more Things To Do Boston! 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 – visit some of the city’s famous museums.


New York – Boston Itinerary

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

If you are planning an itinerary that includes both Boston and New York, start with our 1-Week New York Itinerary – then get all our top 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 Travel Tips For Trips in Boston

View of Boston Skyline from Constitution Dock

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


Organizing Boston Weekend Getaways

There are a lot of details to consider when planning quick Boston getaways. In addition to figuring out what to see and do, travelers are also tasked with determining how to get there and where to stay. Besides the above itinerary of things to do in Boston for a weekend, we share trip planning tips in the next sections, as well. 

As you begin to make your plans and reservations for your Boston weekend getaway, you need to stay organized. We recommend using a travel planner – like our Trip Planning Printables – to help organize the details of your weekend getaway in Boston. 

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When To Visit Boston

One thing to consider when planning a Boston trip is when to go. Personally, we think autumn is the best time to visit Boston – but there are reasons for visiting Boston in every season! 

Summer is a fantastic time for a Boston visit. The weather is usually sunny and dry and the days are long – which is ideal for sightseeing. Plus, the Red Sox are playing. However, Boston summers can get hot and humid – and the city can feel crowded. Additionally, prices for hotels and flights tend to peak during the summer months. 

The fall is an ideal time for exploring Boston. With slightly cooler weather and fewer fellow tourists, it is delightful to explore Boston on foot during the autumn months. In early autumn, visitors can still catch a Red Sox game, too. The fall is also a fantastic time to delve into the spooky side of Boston (the Nighttime Ghost Trolley Tour is fun – get the details here!).

Many travelers dismiss the idea of visiting Boston in winter – but it can be a very romantic time to see the sights. Although the weather can be brisk (or downright cold!), it is perfect for cozying up in a classic tavern, ice skating at Boston Common and visiting the best museums in Boston. 

Springtime in Boston can be hit or miss. Travelers who go to Boston in the spring will beat the crowds (and likely find better prices, too). If the weather cooperates, it is a great time to see Boston and enjoy the spring blossoms!


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 Logan Airport to Boston via The T public transportation. In fact, from the airport, the best way is to take the free Silver Line SL1 Bus into Downtown Boston. The last stop is South Station, which has Boston subway and other bus connections. 


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. A central location will put you within steps to our outlined activities of what to do in Boston in 3 days. 

There is a wide range of Boston accommodations – from 4-star hotels to Airbnb apartments that visitors can choose from. 


Boston Airbnb

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. 

That said, on a short Boston weekend trip, it might not be the best option. Fees can add up quickly and it can be time-consuming coordinating check-in with your host. 


Weekend Itinerary Boston Hotels

We think staying in a hotel is ideal on a weekend trip to Boston. While hotels do tend to be pricey, weekend Boston visitors can sometimes score a deal on downtown hotels that typically cater to business travelers. 

Top choices for the best location include Club Quarters (an affordable option in the heart of town) 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 and can be a fun place to stay for Boston weekends. 


What To Pack For Your Trip to Boston

Packing for a trip can be a chore! We share our best tips for packing on our Ultimate Packing List, but have a few specific packing tips for your trip to Boston as well. Need a Packing Checklist? Get your FREE Packing Checklist here


Weekend in Boston 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 for the weekend, 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 for the Best Photos of Boston

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 weekend getaway to Boston.

Rather than attempting to capture the 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, it comes with a complete kit, which is perfect for beginner photographers!


Weekend Trip Boston Day Bag

Whether you travel with a backpack or a suitcase, you will definitely want a great day pack for your Boston trip. We like to carry small backpacks for all our adventures – as it is the perfect place to stow, organize and secure our phones, keys, camera and all of the other essential, everyday travel items.


Travel Insurance for your Boston Weekend Trip

Trip insurance may cover you in the event of cancelled flights and lost luggage – or if you get sick or injured on your vacation. Consider traveling protected with 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 and check out our Top Underrated US Spots!

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 venturing out West in the USA? Be sure to read our detailed guides to Oregon, California and Montana. How about a Weekend in San DiegoSan Francisco, or the Mile High City of Denver? We also have great tips for visiting Seattle, Portland, OR or Vancouver WA or an adventure in Malibu, Phoenix or 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