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 you can get a taste of all the city has to offer!
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Planning a Weekend Trip to Boston Itinerary
When we spent a long weekend in Boston, it wasn’t our first trip to the city. Far from it, actually. However, our previous visits had revolved around sporting events.
While one of the best things to do in Boston, we missed out on some of the top sights. This time, we arrived with plans; big plans to see the Best of Boston!
Needless to say, we were ecstatic to finally have a complete Boston 3-Day Itinerary. Now, we are sharing those details with you!
Pro Tip: Get (and stay) organized for your Boston getaway with our Travel Planning Printables!
3-Day Boston Itinerary
Our long weekend trip plan includes 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 for your trip to New England!
Day 1: Freedom Trail, Landmarks and Fenway
Begin your Boston Weekend Itinerary with historic spots, local eats, lush parks and the Red Sox! After getting situated in your accommodations (suggestions below), start by visiting top Boston sights.
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 significant sites – all of which played a role in shaping the Untied States of America.
Our 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 it makes more sense this way. The order doesn’t actually matter. In fact, you can just pick and choose which stops you want to make!
Freedom Trail Route
Our recommendations is to begin your Freedom Trail Walk at Bunker Hill.
- Bunker Hill – An obelisk monument marking the first battle of the Revolutionary War. You 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 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 he lived in the late 1700s.
- Faneuil Hall – The site of America’s first ‘Town Hall Meeting’ and 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 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 US, 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 the Massachusetts government since 1798.
- Boston Common – The city’s first (and best) green space!
Freedom Trail Tour or Self-Guided Walk?
Now you 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.
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 likely not have the opportunity to go inside all the sights.
You can also opt to do a Self-Guided Freedom Trail Walk. The route is fairly easy and well-marked. Plus, all 16 destinations include informational plaques and you can download this audio guide.
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.
Lunch on the Freedom Trail
There are plenty of places to eat along the route, but we do have a few suggestions. All of our recommended Boston restaurants for lunch are in North End or Downtown.
Part of the massive Faneuil Hall complex, Quincy Market dates to the mid-1800s and today it is packed with many excellent eateries.
We love the classic pubs in Boston – and The Bell in Hand Tavern is widely considered to be one of the best. And for good reason!
Located along the Freedom Trail (but not an official stop), it claims to be the oldest tavern in America.
If you are looking for a scrumptious seafood lunch, then a ‘Lobstah’ Roll is the way to go! These two restaurants in Boston are well-known for their rolls: Neptune Oyster or Pauli’s in North End.
A bustling, indoor venue, Boston Public Market features 30 vendors specializing in New England products. It is also just across the street from The Bell in Hand.
Boston Common
Now that we’ve sorted out lunch, you 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 into Boston Public Gardens.
They opened in 1838 and were the first botanic gardens in the US. The two most popular sights are the Swan Boats and the Make Way for Ducklings statue.
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.
The area also thrives as a commercial hub and is one of the top shopping destinations in Boston. At its heart is Copley Square, which is where the famed Boston Public Library stands.
Other significant Back Bay structures include 200 Clarendon (formerly the John Hancock Tower), Trinity Church and the Prudential Tower.
Top Tip: Get an overview of the Freedom Trail and Back Bay on this 2-hour guided tour.
Red Sox Game
This wouldn’t be the Best Boston Itinerary if we didn’t include watching the Sox! Built in 1912, Fenway reigns as the oldest MLB ballpark. It’s also one of the smallest, so buy tickets in advance!
If the Red Sox are away or it’s the off season, you can take a Fenway Park Tour instead. It is an absolute must for baseball fans!
Pro Tip: You can catch a glimpse of the action from the iconic Bleacher Bar. Occupying the former visiting team batting cages, it is situated beneath the bleachers with a window on the outfield.
More Evening Boston Entertainment
Baseball isn’t the only sport in the city! The Celtics (basketball) and Bruins (ice hockey) play at the TD Garden. The New England Patriots (NFL) take the field in Foxborough at Gillette Stadium.
Not a sports fan? No problem! 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, this Ivy League school is just a short jaunt away. Simple to reach using public transport, it’s a must on your 3 Day Boston Itinerary.
You can plan to just wander the campus, but don’t miss the top sights, like Harvard Yard, Memorial Hall and Harvard Square.
Top Tip: If you’d prefer not to discover Harvard on your own – join an informative student-guided tour!
Beacon Hill
Perhaps the most picturesque neighborhood in Boston, Beacon Hill 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.
From here you can also embark on the 1.5-mile Black Heritage Trail. The 10-sight route celebrates the history of the Black community and explains events that took place during the American Civil War.
South Boston
Next up 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.
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.
Summertime visitors might consider heading to one of the South Boston beaches. Carson and Pleasure Beach are our two top picks for sunbathing – but any stretch of the shoreline is fun to explore!
Boston Brewery Tour
The city has a long and interesting history with beer. So naturally, hoisting a few pints should be on your list!
The classic taverns and historic brewpubs – some of which date to 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. You can create a DIY brewery tour for your Weekend in Boston Itinerary with this list.
However, joining an organized Boston brewery tour can be a lot fun, too! 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 visiting the aquarium. Next, get a taste of clam chowder, then head out on the water and finish up in buzzing Seaport.
New England Aquarium
Located on Central Wharf, this 4-level facility features a massive fish tank and a variety of sea life. Top draws are the penguins, seals and the you-can-touch tidepools.
Tickets can be purchased at the entrance, but admission is included with the Boston CityPass. The card is also valid for harbor cruises, the Museum of Science and other Boston tourist attractions.
Clam Chowder at Boston Sail Loft
There are countless restaurants to get a good bowl of ‘chowda’, 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 – and the absolutely decadent potato skins.
Boston Duck Boat Tour
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!
These tours use replica World War II amphibious road-and-waterway DUKW vehicles. They are able to take you for a spin around the streets and then a cruise on the river.
The narrated excursion offer a unique vantage point to top landmarks while perched above the streets and on the Charles River.
Other nautical options include a classic Boston Harbor Cruise or this popular Whale Watching Tour. Whichever you choose, it’s the perfect final activity for your Boston Itinerary!
Seaport District
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 enclave.
Seaport also features more than 80 places to eat, making it one of the top dining destinations in Boston.
Home to numerous seafood restaurants, we recommend eating at one of the highly rated spots, like The Barking Crab, Row 34 or Legal Sea Foods Harborside.
For after-dinner drinks, grab a swing at The Lawn on D, a cocktail at Lucky’s Lounge or a pint at Harpoon Brewery. Cheers to Boston!
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 on their visit!
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 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 venues 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 exhibits are displayed in her beautifully designed, Venetian-inspired mansion.
Martha’s Vineyard
A summer colony for celebrities and the wealthy, MV is a beautiful place to see. On this full-day tour, you travel by mini-coach along the coast to Cape Cod, then board a ferry to the island.
Once on Martha’s Vineyard, you can choose to explore on your own or upgrade to a guided experience.
Plymouth Colony
Take a day trip from Boston back in time! Visit the Plimoth Plantation – a recreation of the 17th century colony established by the Pilgrims.
Then see Plymouth Rock – where the English colonists landed, and other historical sites on this all-day excursion.
Salem, Massachusetts
Well-known for the infamous Salem Witch Trials of 1692, Salem is a lovely coastal town today. You can make the trip using the convenient ferry and then join a walking tour once there.
Boston Travel Tips
Now that you know how to visit Boston for 3 days, we have some honest advice and important packing hacks!
When To Visit Boston
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!
Fall is an ideal time for exploring Boston. With cooler weather and beautiful foliage, autumn is also a fantastic opportunity to delve into the spooky side of the city on the Nighttime Ghost Trolley Tour!
Many dismiss the idea of visiting Boston in winter – but it can be very romantic. Although the weather will be brisk, it’s perfect for cozying up in a classic tavern, ice skating at the Common and visiting museums.
Springtime can be hit or miss. If the weather cooperates, it is a great time to enjoy the blossoms flowers. The Boston Marathon also takes place in April on Patriot’s Day.
How To Get to Boston
On our Boston weekend trips, we have always flown into Logan International Airport. Read our hacks for getting the best airfares, then start your search for flights to BOS on SkyScanner!
To get from Logan Airport into the city via public transportation, take the free Silver Line SL1 Bus to downtown. The last stop is South Station, which has subway and bus connections.
Where To Stay in Boston for a Weekend Trip
Staying in a centrally located hotel is ideal on a weekend Boston trip. While they do tend to be pricey, you can sometimes score a deal on properties that typically cater to business travelers.
Top choices include Club Quarters (an affordable option in the heart of town), Omni Parker House Hotel (a luxury stay that is close to everything) and the hip CitizenM near North Station.
What To Pack for a Weekend Trip to Boston
Packing can be a chore, but it’s an inevitable aspect of traveling. So, grab your FREE 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 Boston for the weekend trip, 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 itinerary, we cover some ground! Be sure to pack comfortable travel shoes. Flat, rubber-soled shoes – like these New Balance trainers for women or Merrell trail shoes for men – are what we wear.
Travel Camera
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.
Day Bag
Whether you travel with a backpack or a suitcase, you will also want a great day pack. We carry these small backpacks, they are perfect for securing all of our everyday travel items.
Start planning your US Trip! Search for the lowest airfares, the best accommodations and fun things to do…then start packing! Want additional advice? Head over to our Travel Planning Page and for country-specific information, take a look at our Travel Guides Page!
More USA Destinations
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!
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