Welcome to JetSetting Fools, here you will find our best travel tips for destinations worldwide. Some of the links on this site are Affiliate Links and if you use them to make a purchase, we may earn a commission. For more information, read our Disclosure Policy.
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 travelers can get a taste of all the city has to offer!
Weekend Trip to Boston Itinerary
One of the great things about Boston is that it is fairly compact and walkable. Our Weekend in Boston Itinerary is designed to insure you see the top sights and partake in the best events.
We highlight top Boston attractions and intriguing neighborhoods – as well as historic places and iconic 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? For our weekend getaway, we outline the best way to see Boston in 3 days. We believe visitors can squeeze the top things to do in Boston into a well planned 3 day trip.
Our 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 also be used for weekday visits.
Furthermore, we understand that not everyone is planning 3 days for Boston weekends. Some people are limited to visiting Boston in a day, while others are trying to plan a 5-Day Boston getaway. To help fellow travelers, we outline several sample 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. Far from it, actually. 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 some of the top sights.
On this weekend 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 great neighborhoods and dining on local fare.
Armed with this detailed plan, 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!
3-DAY BOSTON ITINERARY
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 our Boston Travel Guide to plan your trip to New England!
Day 1: Freedom Trail, Famous Landmarks and Fenway Park
Day 1 of your Boston Weekend Itinerary is all about historic spots, local eats, lush parks and the Red Sox! After getting situated in your accommodations (suggestions below), start your trip by visiting top Boston sights and taking in a baseball game at famous Fenway Park.
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 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
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 backwards, but we believe that it makes more sense to complete the route in reverse. The order of the stops doesn’t actually matter. In fact, you can pick and choose which sights you want to see if you have other interests for things to see in Boston in three days.
Freedom Trail Route and Sights
Our recommendations 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 for your Weekend in Boston?
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.
Guided Tour of Boston
An engaging guided tour – like this one – features a local 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 the opportunity to go inside some of the sights.
Boston Self-Guided Walk
Visitors can also opt to do a Self-Guided Freedom Trail Walk. The route is fairly easy to follow – as it is marked by a red stripe through the streets of Boston. Plus, all 16 Freedom Trail destinations include informational plaques. For more interesting facts along the way, you can download an audio guide.
Those 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: If you choose to complete the route in the opposite direction, just make your way back to Boston Common using the subway (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 suggestions. All of our recommended Boston restaurants for lunch are in the North End neighborhood along the Freedom Trail route.
Quincy Market
Faneuil Hall is an official stop on the historical Freedom Trail. Part of a complex of buildings called Faneuil Hall Marketplace, it also includes the Quincy Market. The historic Boston marketplace dates to the mid-1800s and today it is packed with many famous eateries.
The Bell in Hand Tavern
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
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 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 Public Garden
Anyone visiting Boston in a weekend will want to spend some time on the Common. Established in 1634, it’s the oldest park in the USA. Stroll through the space from east to west, passing by the popular Frog Pond and walk into Public Garden.
Boston Public Gardens is a botanical garden (the first in America) and opened in 1838. The two most popular sights 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 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 the John Hancock Tower), 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 legendary Fenway Park. Built in 1912, Fenway reigns as the oldest MLB ballpark. It’s also one of the smallest so be sure to buy tickets in advance!
If the Red Sox are 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!
Pro Tip: You can catch 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.
More Evening Boston Entertainment
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. The New England Patriots (NFL) 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 Boston Theater District watching a theatrical performance or comedy show.
Day 2: Harvard, Cool Districts and Boston Beer
Today you’ll visit one of the most prestigious University campuses in the world, explore iconic neighborhoods and end the day on an brewery tour.
Harvard
Impressive and classic, the Ivy League Harvard campus is just a short jaunt from Boston. Simple to reach using public transport, it’s a must 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: If you’d prefer not to discover Harvard sights on your own – join an informative student-guided tour to all the important spots!
Beacon Hill
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 great spot for lunch and a beverage.
Pro Tip: Visitors to the Beacon Hill neighborhood can also embark on the 1.5-mile Black Heritage Trail. The 10-sight route features houses and buildings that celebrate the history of the Black community and explains 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
Next up on your Boston visit is the once rough and tumble neighborhood of Southie. Made famous in movies like Good Will Hunting and The Departed, the area has seen a flurry of gentrification in recent years. Southie 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 Dorchester Heights and the Monument, Joe Moakley Park and Medal of Honor Park. The Harborwalk, a 40-mile coastline path, connects Southie east to Pleasure Bay and Castle Island and south to the UMass Boston campus.
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 naturally, 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 a hefty number of Boston craft breweries where you can take a tour and get a taste as well. You can create a DIY brewery tour for your Weekend in Boston Itinerary with this list of breweries.
However, joining an organized Boston brewery tour is likely a lot more fun! Evening beer tours – like one of these – include samples, transportation and dinner.
Day 3: Boston on the Water
On the final day of your Boston trip itinerary, start off exploring the New England Aquarium. Next, get a taste of clam chowder, head out on the water and then eat a divine seafood meal on Boston Harbor.
New England Aquarium
A must-see in Boston for 3 days, the New England Aquarium is a top attraction. The site 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. The card is also valid for harbor cruises, the Museum of Science and other Boston tourist attractions.
Lunch of Clam Chowder at Boston Sail Loft
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 to a mix of locals and tourist.
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 decadent 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 sit back, relax and enjoy a ride. Wrap up your fun weekend in Boston on a Duck Boat Tour!
The famed Boston Duck Boat Tours use replica World War II amphibious road-and-waterway DUKW vehicles. They are able to take tourists for a spin around the streets and then a cruise on the river. The narrated tours offer a unique vantage point to some of Boston’s top landmarks while perched above the streets and on 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. Options include the historic Boston Harbor Cruise (get the details) or 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 harbor front is a mixed-use Live, Work, Play district.
Seaport also features more than 80 places to eat, making it one of the top dining destinations in Boston. Home to numerous Boston seafood restaurants, we recommend eating at one of the city’s highly rated spots, like The Barking Crab or Legal Harborside.
Going out in Boston Seaport isn’t only about eating! For after-dinner drinks, head up to the swanky Lookout Rooftop and Bar or grab a swing at The Lawn on D. For something a little more down to earth, check out Harpoon Brewery.
More Things To Do in Boston, Massachusetts
We’ve highlighted the best activities in our Boston Weekend Itinerary, but fellow travelers may want to include these alternate attractions on their visit.
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 neighborhood 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!
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 space ranks as one of the largest art museums in the world with collections that span centuries.
Isabella Stewart Gardner Museum
From the late 1800s through the early 1900s, Isabelle Stewart Gardner amassed an impressive collection of art works. These include 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 more to see in New England! 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 a few of the most popular.
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. Then see 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 far from Boston. Visitors can make the trip from Boston to Salem on their own using the convenient ferry and then join a walking tour once in Salem.
How Many Days to Visit Boston?
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. That said, to really get a good feel for it, we believe 3 days in Boston is ideal. That’s not to say if you are limited to a Boston One Day Itinerary you should skip it. Even with limited time, our sample itineraries will show you how to visit Boston!
Boston in 1 Day Itinerary
For a One Day Boston Itinerary, we recommend following Day 1 from above. If there is no sporting or cultural event during your visit, instead take the Brewery Tour or a Boston Food Tour.
Pro Tip: Visitors pressed for time can streamline their One Day in Boston Itinerary with a convenient self-guided tour on the extremely popular Boston Trolley!
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 in 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 Days 1 and 3 from above. The aquarium and boat trip will likely be more interesting to kids than neighborhood discovery.
Boston 4-Day Itinerary
To plan a Boston Itinerary for 4 Days, we recommend using our detailed outline for 3 days, then add one of the top Boston day trips. 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 Itinerary 5 Days
To create a 5 days in Boston Itinerary, we recommend using our above suggestions for 4 days then visit some of the city’s famous museums. You could also attend another event or take an additional day trip!
New York – Boston Itinerary
Since New York City and Boston are in close proximity, they make perfect destinations to combine on an US East Coast Trip.
If you are planning an itinerary that includes both Boston and New York, start big with our 1-Week New York Itinerary – then get all our advice on 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
Now that you know how to visit Boston in 3 days, we have a few final travel tips and packing hacks for your trip!
When To Visit Boston
One thing to consider when planning a Boston trip is when to go. Personally, we believe autumn is the best time to visit Boston. However, 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. 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. The fall is also a fantastic time to delve into the spooky side of Boston on the Nighttime Ghost Trolley Tour!
Many travelers dismiss the idea of visiting Boston in winter – but it can be very romantic. Although the weather will be brisk, it is perfect for cozying up in a classic tavern, ice skating at Boston Common and visiting the excellent museums.
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 flown into Boston Logan International Airport. Read our hacks for the best airfares, then start your search for flights to BOS on SkyScanner!
Boston Airport to Downtown Boston
To get from the Boston Logan Airport into the city, visitors can use public transportation, Uber/Lyft, private transport or shared transport.
To get from Logan Airport to Boston via public transportation, it’s best 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 believe the best place to stay in Boston is downtown. 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 luxury properties to Airbnb apartments to budget hotels.
Boston Airbnb
Generally, we prefer staying in Airbnb apartments. 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. Airbnb fees can add up quickly and it can be time-consuming coordinating check-in and check-out with your host.
Weekend Itinerary Boston Hotels
Staying in a hotel is ideal on a weekend trip to Boston. While they 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 can be a chore! Be sure to read our Ultimate Packing List, but we have a few specific packing tips for your trip to Boston as well. Grab your FREE Packing Checklist and let’s get started!
Boston Weather 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, be sure to pack clothing that can be layered. Regardless of the season, bring a travel umbrella or packable raincoat.
Durable Walking Shoes
In our 3-Day Boston Itinerary, we cover some ground! Be sure to pack comfortable travel shoes for your trip. Flat, rubber-soled shoes – like these Columbia shoes for women or Merrell trail shoes for men – are what we wear while walking Boston city streets.
Travel Camera
As one of the most historic cities in America, Boston is gorgeous. If you are anything like us, you will be snapping a ton of pictures during your weekend getaway to Boston.
Rather than messing with your phone, we recommend upgrading to an actual camera. We use a Canon Rebel with a 18-135mm lens that takes great pictures…and it is easy to use! Best of all, it comes with a complete kit, which is a perfect budget option 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 these small backpacks for all our adventures. They are perfect for securing our phones, keys, camera and all of our everyday travel items.
Start planning your trip to Boston, USA! Search for the lowest airfares, the best accommodations and fun things to do…then start packing! Want more travel advice? Head over to our Travel Planning Page for 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 Weekend Trips and check out our Top Underrated US Spots!
Are you venturing out West in the US? Be sure to read our detailed guides to Oregon, California and Montana. How about a Weekend in San Diego, San 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!
Pin it! See all of our travel pins on our JetSetting Fools Pinterest Board.
