Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary

Post Published October 23, 2023

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Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Getting Around Boston

Boston is an extremely walkable city, especially the areas you’ll likely be spending most of your time in as a tourist. The city’s main historic sites, museums, restaurants, and attractions are clustered fairly close together. For example, you can easily walk from the waterfront over to Beacon Hill and Boston Common in about 15 minutes. So relying on your own two feet is often the easiest and most enjoyable way to get around.
The city also has a solid public transportation system that can help you efficiently get from point A to point B. The “T”, as Bostonians refer to the MBTA subway and bus system, can get you to most places you’ll want to go as a visitor. It consists of four color-coded subway lines (Red, Orange, Green, and Blue) as well as key bus routes.

The most tourist-friendly stops on the T include Park Street (Red/Green lines), Downtown Crossing (Orange/Red), and Government Center (Green/Blue). These stops put you right in the heart of major attractions like Faneuil Hall/Quincy Market, Boston Common, and Beacon Hill.

If you plan on using the T a lot, purchasing a CharlieCard is highly recommended. The reusable plastic card can be loaded with money and offers a discounted fare over paying with cash. CharlieCards can be purchased at most T stations.
In addition to the T, Boston has an extensive above-ground trolley system that is especially convenient for getting from downtown hotels to the Seaport district and convention centers. Look for the Silver Line SL1, SL2, and SL3 routes. The trolleys come frequently and are free to ride.
Taxis and rideshares like Uber/Lyft are plentiful in the city. However, Boston’s notorious traffic congestion can make them slow and expensive options. Use them sparingly or for late night transportation when the T stops running.
If you want to travel beyond the city center, the commuter rail can take you to charming towns like Salem, Concord, and Rockport. The lines heading south and west from South Station tend to be the most popular for visitors. Purchase tickets ahead of time on the MBTA website for the best fares.
Finally, for longer day trips out of the city, Boston has three major bus depots: South Station, Logan Airport, and the brand new South Boston Waterfront bus terminal. From these hubs you can catch buses to Cape Cod, New York City, and other popular destinations in New England. Most buses allow you to purchase tickets online and offer free wi-fi on board.

What else is in this post?

  1. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Getting Around Boston
  2. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Top Sights and Museums
  3. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Freedom Trail and Historic Sites
  4. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Harbor Highlights
  5. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Foodie Favorites
  6. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Nightlife and Entertainment
  7. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Day Trips from Boston
  8. Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Where to Stay in Boston

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Top Sights and Museums

Making the Most of 3 Days in Beantown: The Ultimate Boston ItineraryWith only 72 hours to experience Beantown, you’ll want to make the most of your time and hit the highlights. Boston’s rich history and world-class museums simply can’t be missed.

No first-time visit to Boston is complete without walking the Freedom Trail and taking in sights like the Old State House and Faneuil Hall. Wandering the cobblestone streets of Beacon Hill and admiring the charming gas-lit lanterns is like stepping back in time.

Of course, you’ll also want to spend some time in the charming towns across the Charles River like Cambridge and Somerville. Harvard Square is a must-see, even if you don’t pop into the university itself.

The Museum of Fine Arts, Boston is one of the best art museums in the country. Its collections span everything from Monet paintings to ancient Egyptian artifacts. Give yourself at least 3 hours here to take it all in.

A short walk away is the Isabella Stewart Gardner Museum - a personal favorite of mine. The intimate galleries and central courtyard full of flowers make you feel like you're visiting a wealthy friend's private home, which is exactly what Mrs. Gardner intended when she built this stunning palazzo.
Fans of American history (and beer!) shouldn't miss the Samuel Adams Brewery and museum. Take an interactive tour highlighting Boston's brewing heritage and see how the famous Sam Adams lager is made. You'll get free samples too!

If you have kids or are still a science geek at heart, the Museum of Science right near the Charles River is also excellent. With interactive exhibits on everything from engineering to dinosaurs, you're guaranteed to learn something new.

To dive into Boston's maritime past, walk the Freedom Trail to the USS Constitution Museum next to the historic warship herself. Then head to the Charlestown Navy Yard to explore the World War II destroyer USS Cassin Young and other naval exhibits.

Of course, no trip to Boston is complete without reliving a bit of the American Revolution. The Paul Revere House lets you step back in time to the colonial era and hear the tale of the famous midnight ride.

With sunshine and warm spring weather, the glorious Public Garden and Boston Common are also not to be missed. See where the Freedom Trail starts and snap a photo of the famous bronze duckling statues from Make Way for Ducklings.

Ortiz jerseys may be hard to find after his recent retirement, but baseball history lives on at Fenway Park. If you can, splurge for stadium seats or at least take a tour for a behind-the-scenes look. Even if you’re not a sports fan, you can’t visit Boston without setting foot inside the iconic ballpark.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Freedom Trail and Historic Sites

No first-time visit to Boston would be complete without following the famous Freedom Trail. This 2.5 mile walking trail winds through the heart of Boston, connecting 16 key historic sites related to the American Revolution and founding of the United States.

As a history buff and patriot at heart, I knew exploring Boston's pivotal role in America's fight for independence was at the top of my must-do list. The Freedom Trail provides the perfect framework, neatly guiding you to all the major sites so you can immerse yourself in the past.
I started my journey at Boston Common, where the first leg of the trail begins. As I gazed at the golden dome of the State House shimmering in the morning sun, I felt a rush of excitement for the day ahead.

My first stop was the iconic Faneuil Hall, a marketplace and meeting hall that earned the nickname "Cradle of Liberty" for its role fomenting the Revolution. Though the shops and restaurants cater largely to tourists today, you can still feel the history in these halls. I watched a National Park Service ranger give an animated retelling of Samuel Adams and other rabble-rousers rallying the crowds against British rule.
Next up was the Old State House, the oldest surviving public building in Boston. It was here that the Declaration of Independence was first read aloud to jubilant crowds. I marveled at the balcony and lion and unicorn statues, imagining the impassioned speeches given over 200 years ago.
No Freedom Trail experience is complete without seeing the Old North Church, made famous by Paul Revere and his legendary midnight ride. I loved scouring the church's interior for clues commemorating that pivotal event. Outside, I paused to appreciate the tranquility of the gardens and reflecting pool - a peaceful contrast to the conflict and turmoil that once surrounded this site.
Of course, a quintessential Boston experience is meandering the cobblestone streets and gas-lit lanes of Beacon Hill. Walking past stately brick row houses and peering at Mount Vernon Street's charming window boxes evoked a true sense of history for me. It felt like traveling back in time to the 19th century as I wandered past Louisburg Square.
Ending my journey at the Bunker Hill Monument provided dramatic views across the Charles River. Climbing the obelisk's 294 steps left me winded but rewarded with panoramic vistas. Reading the engraved names of the fallen patriots was a poignant reminder of the sacrifices made for freedom.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Harbor Highlights

Boston's bustling harbor is so much more than just a pretty backdrop for postcard photos. This historic waterfront is the lifeblood of the city and has shaped Boston's destiny from its earliest days. Three days is barely enough time to scratch the surface of all the maritime magic waiting along Boston's banks. From tall ships to seafood feasts, you'll want to spend as much time as possible down by the water.

No harbor highlight tour is complete without some time on the water itself. Several Boston companies offer narrated cruises that give you a unique vantage point of the city and surrounding islands. Whether you choose a posh champagne brunch, a sunset sail, or a hands-on historic adventure, you're guaranteed incredible views of sights like the Bunker Hill Monument, USS Constitution, and the iconic Custom House Tower.
One of my favorite ways to soak in that salty sea air is by ferry. Boston Harbor Cruises runs several routes that connect downtown to charming coastal communities like Salem, Provincetown, and Plymouth. Spend some time strolling the historic streets and beaches across the harbor before catching the last ferry back.

Back along the bustling Boston waterfront, no visit is complete without a stroll along Long Wharf and the newly renovated Harborwalk. Watching the colorful ferryboats and swift catamarans zip off to the Harbor Islands is a treat. Don't forget to glimpse the iconic Custom House and snap some photos of the stunning waterfront views.
Of course, you can't talk Boston history without considering the pivotal role of tea - as in the infamous Boston Tea Party. Visit the replica tall ship Beaver and meet re-enactors portraying the Sons of Liberty to get the real story behind the rebellion. Nearby is the Boston Tea Party Museum, where you can even dress up and join in on a re-enactment yourself!

After soaking up all that history, stretch your legs with a walk across the Charlestown Bridge to savor sweeping panoramas of the harbor and skyline. Then reward yourself with an ice cream cone as you meander the USS Constitution Museum grounds.

No harbor tour is complete without scoping out Faneuil Hall and Quincy Market's food hall. The bounty of Boston's waters awaits you here, from heaping bowls of chowder and lobster rolls to the freshest raw oysters and langoustines. Don't miss Mike's Pastry for decadent cannolis and other Italian treats.
After stuffing yourself to the gills, work off those calories with a stroll along the Rose Fitzgerald Kennedy Greenway. Kids and kids-at-heart will love playing in the Rings Fountain. As evening approaches, follow the glowing lights of the Harbor Garage Pedestrian Bridge back to the waterfront.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Foodie Favorites

As a self-proclaimed foodie, I couldn’t wait to bite into all the culinary delights that define Boston’s eclectic dining scene. From lobster rolls to cannoli, Boston’s signature dishes reflect the city’s multicultural heritage and seaside location. With only 72 hours to spare, I had to be strategic in choosing the most iconic restaurants and mouthwatering menus.

No first-timer’s visit to Boston is complete without tearing into a freshly grilled lobster roll, best enjoyed with a cold craft beer along the waterfront. Every local has their personal favorite lobster shack, but Island Creek Oyster Bar, Yankee Lobster, and James Hook & Co. came highly recommended. I was not disappointed by the overflowing piles of sweet, tender meat bursting with flavor. For the ultimate experience, time your lobster roll lunch or dinner with a harbor cruise at sunset.

Of course, you can’t discuss Boston cuisine without mentioning the city’s beloved baked beans. This classic Yankee dish gets a modern twist at retro dining institutions like Durgin Park, which has been dishing out pots of molasses-laden beans since 1827. The signature crusty cornbread and Indian pudding make perfect accompaniments. Just leave room for Boston cream pie – the official state dessert.

No weekend morning is complete in Boston without grabbing a dozen doughnuts and a large coffee. Locals swear by their neighborhood bakeries, but as a tourist, I made a beeline straight for Kane’s Donuts. With both traditional and gourmet flavors, it was love at first bite. Try the decadent crème brûlée doughnut for an unforgettable breakfast indulgence.

Boston is also home to the historic Faneuil Hall Marketplace, more commonly known as Quincy Market. The lively food hall makes grazing on local specialties a breeze. I enjoyed sampling Greek dips at Para Doe, steaming bowls of chowder from the Boston Chowda Co., and fresh-shucked Island Creek oysters. Don’t miss the chance to watch expert flippers grill up pad Thai at BAO BAO or load up on Italian treats from Mike’s Pastry.
Of course, if you want to experience where Bostonians really eat and drink, get out of the touristy downtown area and head to some local favorites. In the North End, twinkling lights and old-school charm drew me into cozy restaurants like Giacomo’s Ristorante for heaped plates of pasta and Legal Sea Foods for seafood straight off the boat.

Farther afield in Cambridge, I joined the crowds queued up outside Mr. Bartley’s Burger Cottage, whose juicy gourmet patties demand your attention. And I couldn’t visit Boston without popping into the historic Union Oyster House for chowder served in a bread bowl, just like Daniel Webster himself used to order.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Nightlife and Entertainment

After long days spent pounding the Freedom Trail pavement, my weary feet were eager to let loose and delve into Boston’s renowned nightlife. From cozy Irish pubs to rowdy sports bars, Beantown offers no shortage of options to unwind over frothy pints or fancy cocktails.

No neighborhood captures the city’s quintessential mix of history and revelry quite like the North End. As the sun set over Old North Church, I slipped down narrow alleys to find cellar taverns like the Bell in Hand - America’s oldest continuously operating bar. Squeezing into a tiny wooden booth underneath the flickering gas lamps transported me back in time. I half expected Samuel Adams and other revolutionaries to barrel through the doors as I sipped local craft brews and soaked in the atmosphere.
Of course, a sports-crazed city like Boston offers plenty of lively spots to catch a game. If you want to hang with the locals, Hurley's in Downtown Crossing came highly recommended. With cheap beer specials and walls plastered in memorabilia, it captured that old-school Boston Irish spirit. For a splashier scene, modern bars like Game On! feature giant screens perfect for taking in all the Celtics and Bruins action.

Near trendy Faneuil Hall, I stumbled upon Cheers - a replica of the iconic bar from the classic TV sitcom. Joining other tourists for a spirited rendition of “Where Everybody Knows Your Name” provided an only-in-Boston moment I’ll always treasure. The Bull & Finch Pub, which inspired the original Cheers exterior, is just steps away if you prefer a cozier neighborhood feel.

Of course, Boston boasts no shortage of sleek lounges and hip hotel bars primed for a glam night out. For delicious Prohibition-era inspired cocktails, Beehive Boston's jazz club vibe had me feeling like a flapper. Meanwhile at Downstairs at Henrietta’s Table, moody candlelight and leather banquettes set the scene for their delicious house-made vermouth cocktails.

For a uniquely Boston experience, nothing beats catching a Red Sox home game at Fenway Park. Joining the fanatical crowds to sing “Sweet Caroline” and cheer for the hometown team should be on any visitor’s bucket list. But be prepared to shell out big bucks for seats at America’s oldest ballpark.

Luckily, even teetotalers can soak up Boston baseball lore at Bleacher Bar. This lively watering hole secretly tucks under the Fenway bleachers, offering patrons an awesome view inside the stadium through a giant garage door window. Sipping local brews alongside the Fenway faithful while eavesdropping on sports debates felt like a true insider’s experience.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Day Trips from Boston

As much as I wanted to spend all 72 hours soaking up Boston proper, the historian in me couldn’t resist taking a few day trips to visit the colonial towns surrounding the city. After all, a huge part of appreciating Boston’s pivotal role in America’s founding means getting out of the urban metropolis and into the countryside where the first revolutionary sparks were lit.
At the top of my day trip wishlist was Lexington and Concord. As the site of the “shot heard round the world” that kicked off the American Revolution, a pilgrimage here felt like a must. I joined the Patriots Day reenactors bright and early to watch the sunrise in Lexington before wandering battle sites like the Old North Bridge where the fighting began. Costumed guides expertly set the scene, transporting me back to that fateful morning of April 19, 1775 when brave farmers took up arms against British forces.
After soaking up the past in Concord center, I wandered authoress Louisa May Alcott’s home, Orchard House. As a bookworm who grew up adoring Little Women, I loved perusing Alcott’s original manuscripts and strolling through the lovely grounds. Nearby in Sleepy Hollow Cemetery, I paid respects at Alcott’s grave along with other famed writers like Thoreau and Hawthorne.

For a dose of literary inspiration paired with oceanside tranquility, a day trip up the coast to Cape Ann was just the antidote to bustling Boston. I began in downtown Gloucester, which felt refreshingly real compared to the tourist-swarmed city. At the Rocky Neck Art Colony, I admired the shingled cottages and salty harbor views that have inspired artists for centuries. Seafood lovers can’t miss the Gloucester Fresh Seafood Trucks, clustered right on the wharf, for the island’s famous lobster rolls and clam chowders.

Farther up the cape, Rockport’s stunning beaches and windswept vistas stirred my soul at Halibut Point State Park. I could imagine why this landscape so captivated painters of the early 20th century. Back in Rockport village, Motif Number 1 is the most photographed site on Cape Ann. I tried my own hand at capturing the red fishing shack on canvas with a leisurely outdoor painting class.

Of course, no escape to rural New England is complete without some time spent browsing country stores and farm stands. I stopped into Russell Orchards in Ipswich to taste their just-picked apples and sample fresh cider doughnuts. Their sprawling farm has entertained families for over a century.

Before heading back to Boston, I couldn’t resist detouring through Salem for a dose of witchy history. From the chilling Witch Trials Memorial to the fabulous witch-themed Peabody Essex Museum, this city does Halloween right even in springtime. Costumed interpreters get you into the spooky spirit along the Historical Witch Trail.

Making the Most of 3 Days in Beantown: The Ultimate Boston Itinerary - Where to Stay in Boston

With charm and history around every corner, Boston offers no shortage of accommodations options for visitors. But choosing the right home base is key to making the most of your Beantown getaway. Luckily, the city’s compact size means you can base yourself just about anywhere downtown and still easily access top attractions. It just comes down to selecting the ambiance and amenities that best fit your travel style.
For convenience, it’s hard to beat staying right along the Freedom Trail in the heart of downtown. This puts you steps from Faneuil Hall, Quincy Market, and the harbor, not to mention endless restaurants and nightlife. Boutique gems like XV Beacon shine in historic Beacon Hill amidst gas-lit streets. Meanwhile, the Boxer Hotel sits just across from TD Garden and North Station for game nights or train trips.

Near Boston Common, check out the Godfrey Hotel’s swanky lounge and hip rooftop bar. Or soak up luxury and great city views at the Ritz-Carlton perched overlooking the Common. Family travelers love the Residence Inn for its spacious suites with full kitchens and seasonal rooftop pool.

Across the Charles River in lively Cambridge, boutique hotels like Hotel Veritas put you in the bustling Harvard Square area, rife with restaurants, shops, and culture. For a historic stay, check out the storied Charles Hotel with its jazz club and old-school charm. Or opt for scenic riverside views at the Hyatt Regency nestled alongside the scenic esplanade.
If you prefer being along the water, Boston Harbor Hotel oozes luxury right on the downtown harbor-front. Watch boats glide by through floor to ceiling windows or take a swim in the scenic indoor lap pool. For equally gorgeous harbor views on a budget, the vibrant Seaport Hotel can’t be beat.

Nearby in the lively Seaport District, the luxe Intercontinental and W Hotel anchor the popular waterfront area filled with dining, shopping, and attractions. Baseball fans love staying practically on top of Fenway Park at Hotel Commonwealth, with stadium views from some rooms.

But many discerning travelers prefer to stay outside the tourist zone in Boston's charming neighborhoods. In Back Bay, colonnaded brownstones and stylish boutiques set the scene for accommodations like Colonnade Hotel and Loews Boston. South End oozes trendy, artsy vibes with options like the dual-branded AC Hotel and Residence Inn.

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