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3 Days in Boston: The

Ultimate Weekend
Itinerary for Boston,
Massachusetts
BY CONTRIBUTOR | UPDATED ON: FEBRUARY 9,
2022

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Here’s a fun fact: I (Lia) was actually

born in Boston! I lived there for a grand
total of the first 3 years of my life, during
which most of my memories involved
snow, and the traumatic experience of
losing the leg of one of my favorite
Barbie dolls in said snow. (For whatever
reason, that’s my most vivid Boston
memory as a child. Lame.) Anyway, I’ve
always considered Boston to be an
integral part of my heritage, even if I
outgrew my Boston accent by age 5. I’ve
returned to Boston many times since,
even spending a summer living nearby.

So I was thrilled when Lindsay, a Boston

local, offered to create a 3-day itinerary
for the perfect weekend trip to Boston.
Take it away, Lindsay!

Table of Contents 

BOSTON AT-A-
GLANCE
Here’s a bite-sized snapshot of
everything you need to know to plan
your trip!

When to Go: Visit late April

through June and September
through November. Springtime is
preferable as you’ll get to enjoy
sitting at outdoor patios in nice
weather.
Where to Stay: We recommend
Found Boston Common in the
Theater District, Chinatown’s
neighbor. Inside a Georgian
building, it harkens to 19th
century Boston high society.
How to Get Around: Fly into
Logan International Airport and
catch the free shuttle to the blue
line, or take a Lyft to your hotel.
We recommend using Kayak to
find the cheapest option on your
flights.
Top 3 Highlights: Don’t miss this
phenomenal tour of Fenway Park,
this important Freedom Trail
Tour, and croissant sandwich and
cardamom and honey-halva
house latte from Tatte Bakery
(it’s well worth the line).
Before You Go: You MUST read
The Isabella Stewart Gardner
Museum: A Companion Guide
and History before visting the
museum.

Psst: Planning a trip to Boston? Here are

some other posts that you might find
helpful:

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···

···

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Local’s Guide)
The Ultimate 10-Day New England
Road Trip Itinerary
10 Charming Places to Experience
Fall in New Hampshire
36 Things to do in Hudson Valley,
New York: A Complete Local’s
Guide

By the way: We’ve compiled our

itinerary into a super handy, 1-page
downloadable! Print it out or load it up on
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Boston, Massachusetts in
the Winter (A Local's
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Sailboats on the water in Boston, Massachusetts on a

summer day.

BOSTON INSIDER TIPS

If you’re planning a trip to Beantown,
there are a few things you should know
about locals: most of us don’t say
chowdah, almost all of us run on Dunkin’
Donuts, and none of us approve of the
branding shift to Dunkin’–we all know
they sell more than donuts. We also
know there are far superior donuts out
there.

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You know all that David Ortiz this is our

f***in city! rallying? It’s not just for show.

The Perfect 3-Day Maui Itinerary

Call me biased (I know I am), but I don’t

think there’s a city quite like Boston’s
real-deal, shout-it-from-the-rooftops,
I’m-going-to-wear-sports-jerseys-all-
year-because-Boston pride.

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···

Whether from our founding fathers-era

history, the killer seafood, or intense
rivalry with the Yankees that forces us to
keep our guard up, there is something
about the city that elicits this collective
pleasure of being in it.

It wasn’t until I moved out of the Boston

area (and into arch nemesis territory,
New York) that I could fully appreciate
how dynamic and energetic it is. That’s
the irony of home, I guess… the further
away you are, the more you actually take
in and admire.

Boston is a city defined by its history and

sports culture; a city full of homey,
Cheers-esque bars and a thriving theater
scene; a city that continues to surprise
with refreshing tweaks and additions by
way of twenty-somethings coming,
staying, and offering craft beer.

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···

I love the idea of being a local expert on a

place, and created this 3-day itinerary to
help you see Boston like a local too.

The best time to visit Boston is during the warmer months

of the year: late April to June and September to
November.

WHEN TO VISIT BOSTON

The best times to come to Boston are
late April through June and September
through November.

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···

Springtime is preferable, and here’s why:

no matter where you’re coming from,
you’ll feel the collective sigh of relief
Bostonians let out as we open our
windows to the nice weather, sit at
outdoor patios, and frolic through life
wearing less than three layers of clothes
as we bid another winter adieu.

It’s a very happy time to be here,

because the Duck Boats are back
chugging along the streets, the Public
Gardens are spectacular in a rainbow
burst of tulips, and the cool breeze
drifting off the harbor is something to
relish.

In May, all of the colleges let out, so the

student population (which makes up a
majority of the city’s demographics)
dissipates, and it’s quiet, and you’ll
probably be able to snag a table at that
popular weekend brunch spot (yass).

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···

The fall season in Boston is #basic and

my favorite thing in the world. If foliage is
your cup of tea (perhaps the kind you’d
pour into the ocean? … Boston joke.)
then this is the place to be. Not only is
the city aglow in hues of auburn and
tangerine leaves, but baseball season is
coming to a close, and if the Red Sox are
still in, you’re in for a treat: a real-life look
at the wild and exciting world of Boston
sports.

Boston Calling, a really fun music festival,

comes around every May and
September, too. You’ll be sure to make it
if you come during either of these
seasons!

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···

READ THIS POST

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Washington DC in the
Winter (& Why
You Should Spend
Christmas in Washington
DC)

Head to Boston in the summer to see the sailboat views in

the water!

WHERE TO STAY IN
BOSTON
Boston is not cheap. You unfortunately
won’t find many places that charge less
than $100 a night. Luckily, it is a very
walkable and public transportation-
friendly city, so no matter which
neighborhood you stay in, you’ll still be
within arm’s reach of everything.

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···

If you need a place to store your bags

check out LuggageHero, a service that
helps you find a safe place to keep your
luggage while you’re running around!
Use the code PRACTICALW for 2 hours
of free luggage storage on us.

For budget travelers, there are a couple

of hostels downtown with plenty of
common space, modern design, and an
overall cozy feel. They’re perfect
jumping-off points for your weekend
here!

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···

HI Boston is located in Chinatown,

near the Boston Common,
Downtown Crossing, and the
Boston Opera House. Not only are
you near three train lines, but also
within a 20 minute walk of Beacon
Hill and tourist-favorite Faneuil
Hall. (It isn’t included in this
itinerary, but it is a cool market of
food vendors, but it can be a little
crowded – especially on weekends.)
Found Boston Common is in the
Theater District, Chinatown’s
neighbor. Inside a Georgian
building, the period pieces harken
to 19th century Boston high society
– how else would you want to spend
your trip?

If you are a vacation home kinda person

it is going to get pricey, options for
private apartments are in short supply if
you’re sticking within a reasonable
budget. However, we found this great
apartment in Savin Hill which is a 5-
minute drive to downtown Boston or a
few minutes on the Subway. Savin Hill is
home to young professionals and artists
and has many diverse gastronomy spots
to sample.

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···

Alternatively, if you want to be closer to

downtown Boston check into ‘The Boiler
Room’, a creatively decorated, spacious
basement condo just across from the
metro.

If you prefer to stay in a hotel, we

recommend searching using Kayak, a
price comparison site that aggregates
every hotel “discount” site into one spot,
so you know you’re getting the best deal!

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···

Find Hotel Deals in Boston

Who wouldn’t fall in love with these amazing skyline

sunsets on the Boston Harbor?!

HOW TO GET TO
BOSTON
The northeast is well-connected (I have
always taken for granted just how easy it
is to transverse states and take easy
weekend trips outside of the city or
state, to destinations like New York,
Washington DC or Vermont), giving you
your choice of plane, train, or automobile
to get here! Fly into Logan International
Airport (and maybe pick up a Dunks
coffee), and from there you can catch
the free shuttle to the blue line (more on
the trains below), or take a Lyft to your
hotel. We recommend using Kayak for
price comparison on flights!

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···

Amtrak trains out of North Station and

Greyhound buses out of South Station
run frequently in and out, are perfectly
situated downtown, and have access to
the trains as well.

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George Washington Statue in the Boston Public Garden,

which you’ll visit in our Boston weekend itinerary!

HOW TO GET AROUND IN

BOSTON
There is no easy way to explain the T, as
we so lovingly call the train system, but
be warned: the Green Line is the worst of
them all, and the Blue Line is
(subjectively) the best of them. The rest
run in and out of favor, but generally
speaking they don’t experience too many
delays, and outside of rush hour move
quickly. The main train lines you will be
taking on this itinerary are the green (I
am truly sorry) and the orange lines.

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···

Charlie Tickets (How sweet is that,

Boston named the train tickets!) are
$2.75 per ride. It will depend entirely on
how much you see yourself riding the T:
if you plan on using public transportation
to get from, say, Beacon Hill to the North
End, or are taking the train upwards of
four times in a day. You most likely won’t
hop on that many times, but if you see
yourself doing so then I recommend the
weekly pass. It’s $21.50, which boils
down to about $7.08 a ticket a day, which
is just shy of three rides a day.

There are plenty of Lyfts and Ubers

around, both utilizing shares and pools,
and walking is a viable option. Everything
is so close together to make that
possible!

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···

Now that you’ve got all the tips you need,

without further ado, here’s your ultimate
weekend guide to Boston!

The best experiences in Boston for your

trip

View
Boston Duck Tour: The
Original and World-
Famous
80 minutes

1165 Reviews

View
Boston: Whale Watching
Catamaran Cruise
3.5 hours

1088 Reviews

View
Boston: Historical
Sightseeing Cruise
1 hour

845 Reviews

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···

3 DAYS IN BOSTON
ITINERARY
While I’d recommend staying in the city
as long as you can, 3 days in Boston is
definitely enough to see the main
highlights and some of the favorite local
spots, too! In this post, I’ve combined
some of Boston’s most iconic attractions
with a few local favorites into a nice, neat
little 3 day Boston itinerary.

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···

It’s hard to pin down the best of Boston

in three days but, hey, you’ll just have to
come back!

Fenway Park is one of America’s oldest ballparks. If you

visit during baseball season, you should definitely catch a
game here!

BOSTON ITINERARY: DAY

1
Your first day in Boston will take you to
some of the city’s best museums and
through the neighborhood of Fenway
Park. In the morning, you’ll head to the
Fenway neighborhood via Lyft or the T’s
green line (get off at the Fenway stop)
for coffee and crepes, and then spend
the day checking out two of Boston’s
finest museums. Then, in the evening,
you will be eating a travel-inspired dinner
and reveling in the history of Fenway
Park!

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···

BREAKFAST AT
NEIGHBORHOODS COFFEE
AND CREPES
My sister introduced me to this place,
Neighborhoods Coffee and Crepes,
which is literally her neighborhood crepe
place. I fell in love immediately. The name
gives away everything it is, that is, a quiet
spot for locals to come in, enjoy a freshly
made crepe, and have a cup of joe.

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···

Hazlenut spread and strawberries is a

classic, banana fosters is sweet in
simplicity, and then there’s the
Strawberry Patch: House-made
strawberry rhubarb jam topped with a
house-made lemon custard sauce. Um,
we’re drooling. And those are just on the
sweet roster.

They also have uh-mazing breakfast

crepes of eggs, cheese, and varying
veggies, savory signatures like feta,
mozzarella, arugula, and tomato, and
some with sweet potatoes. I mean, come
ON. Who doesn’t want to make that
magic happen?!

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···

Neighborhoods serves George Howell

Direct Trade Coffee, seasonal coffee
drinks such as a maple latte, and hot
chocolate that just slightly bitter enough
to round out the sweet chocolate. (Do I
sound like a connoisseur yet…?)

Neighborhoods Coffee & Crepes |

Address: 96 Peterborough Street,
Boston, MA

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The courtyard in the middle of the Isabella Stewart

Gardner Museum is designed to look like a Venetian
palazzo. Original photo credit: “A jungle of art” by
Unhindered by Talent

MUSEUM HOPPING
Boston is home to an insane number of
museums in and around the area, like the
Museum of Bad Art in Somerville, but
two that shouldn’t be missed on your
first trip are the Museum of Fine Arts
(MFA) and the Isabella Stewart Gardner
Museum. Whiling away hours in either or
both of these marvels is unavoidable,
and given that they’re so close to one
another, too easy.

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···

The MFA showcases a gallery of works

from the ancient Egyptians to the
Impressionists to the making of the Make
Way for Ducklings children’s book. The
building itself is a marble palace, every
footstep and breath echoed, and
transverses wide rooms with minimalist,
glass-paned hallways. A trademark piece
in the museum is Little Fourteen Year Old
Dancer by Edgar Degas.

Every spring, the MFA celebrates their

annual Art in Bloom festival weekend,
where flower arrangements interpret and
reflect art pieces and collections. Every
area of the museum is included in the
fun, giving a whole new meaning to art
appreciation. Plus, it smells amazing in
there!

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···

You can always expect to find a cool

exhibition going on, allowing you to visit
favorite sections of the museum while
checking out something new.

Museum of Fine Arts | Address:

465 Huntington Avenue, Boston,
MA

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···

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The Isabella Stewart Gardner Museum’s

signature room is the conservatory at the
center of the building, the rest of the
levels wrapping around it as it reaches up
to the skylight.

Isabella Stewart Gardner, a devout

traveler, purchased the building in the
late 1800s, intent on curating a museum
with the objects and artworks she
acquired on her journeys. She moved
into the fourth floor so she could be
close to the design process, all the while
hoping to ignite joy and awe at the world
in Bostonians. There is so much
tranquility, homeyness, and majesty in
her designer’s eye that lends to this
museum doubling as comfort.

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···

Until her death in 1924, Isabella hosted

guests in her private museum (party
people say what?), and on her deathbed
declared that it be opened to the public.
It is a feat of encapsulating art and
passion, and you could probably spend
hours sitting by the garden. Pick up a
companion guide before visiting to get a
deeper feel for the museum.

The museum has also been the victim of

an art heist, where some still-unknown
person stole 13 pieces from the walls.
The empty frames still hang as they were
found the following morning in 1990. And
there’s still a $10 million reward out there
in exchange for information.

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···

History, art, robbery – it’s a thrilling

romance set in the Fens.

Isabella Stewart Gardner Museum

| Address: 25 Evans Way, Boston,
MA

DINNER IN FENWAY
Depending on where you’re staying, hop
on the green T line or take a Lyft out to
the Fenway neighborhood, where hidden
gems are kept as guarded as by a
dragon.

Try Sweet Cheeks for Southern-style

BBQ meals and cocktails inspired by the
sweet teas and whiskey of the South. Or
visit the uber fun graffitied Japanese
izakaya Hojoko, try the Wasabi Roulette
or the sharing menu of tuna ribs and all
the trimmings to make your own hand
rolls. Head on through the vinyl bar at
The Groove for after dinner cocktails.

Fenway Park is home to the Red Sox and is one of the

most wonderful places to wander in Boston!

WALK AROUND YAWKEY

WAY & FENWAY PARK
Yes, it’s stereotypical. No, it never gets
old. Just a seven minute walk from
Tapestry is Fenway Park. One of
America’s oldest ballparks, and the
essence of Boston sports, is a spectacle
in its own right. The chairs are original so,
really, you’re sitting your butt right on
history. Cool, right? You can even book a
tour of the park here.

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···

Fenway Park | Address: 4 Yawkey

Way, Boston, MA 02215

If you’re visiting Boston during baseball

season, definitely catch a game – it’s the
best way to spend a Friday night in
Boston. Even if you aren’t a Boston fan,
to spend the night with a Fenway Frank
in one hand, an overpriced beer in the
other, and singing along to “Sweet
Caroline” around the 7th inning is
electric.

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···

If you find yourself here in the offseason,

a stroll down Yawkey Way is a fun little
detour (apparently the street has now
reverted back to its former name, Jersey
Street). The two scenic blocks outside of
Fenway Park, with a row of World Series
Champion banners fluttering in the
breeze, are emblazoned in the team’s
logo.

Beacon Hill is Boston’s most picturesque neighborhood,

and where you’ll be spending your Saturday morning!
(Photo by Ryan Harvey on Flickr)

BOSTON ITINERARY: DAY

2
Today you’ll be brunching in the
picturesque neighborhood of Beacon
Hill, stocking up on local goods along
Charles Street, and eating your way
through the North End, also known as
Boston’s Little Italy. You’ll cycle or walk it
all off as you follow the Freedom Trail, a
historic self-guided route, and finish the
day back in the North End with seafood
and drinks in a chic new lounge.

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···

Let’s get started!

BEACON HILL &

BREAKFAST AT TATTE
BAKERY
Instagram flatlay opportunities abound at
Tatte Bakery and Cafe. Its first location
opened in Brookline, MA, and the
atmosphere feels aligned with the
neighborhood: laid back, chic, dreamy.
It’s a Brooklyn-ish hub that still feels
distinctly Boston.

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···

A number of locations have opened in

recent years, and the one you’ll make
your way to is in the famed Beacon Hill
district, widely considered to be Boston’s
prettiest neighborhood.

To get there, take the green line to

Arlington. When you emerge, you’ll be
in Beacon Hill.

Ah, to soak in the old world glamour of

Boston’s charmed Beacon Hill, where
rent for a 1-bedroom basement
apartment runs you a pretty penny. Like,
unthinkably expensive. But who cares,
because it’s Beacon Hill!

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···

Insider Tip: October is one of

Boston’s prettiest months to visit,
and Halloween in Beacon Hill knows
no bounds, on decor, candy, or age.
If you dress up, adults are welcome
to explore the neighborhood and
trick-or-treat, suddenly transported
to an era of cobblestones and
street-lamps and potential headless
horsemen running around. Anything
feels possible.

Early on Saturday mornings is one of the

best times to be in the area, because
everyone is still in bed. There’s
something about the sound of your feet
pounding hundreds of years old
pavement, and the way the morning sun
casts its glow on the homes where once
ballgowns and 7-course dinner parties
thrived, that is SO charming.

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···

Once you’ve completed your first round

of oohs and ahs, enter the oasis of
Tatte’s embracing environment and find a
seat among the young families and early
bird laptop clackers.

For such a small place, they pack a huge

punch, with items like croissant
sandwiches, french toast with
housemade challah bread, ricotta and
jam tartines, and monkey bread. They
sell Stumptown Coffee, and even have
their own house latte, swirled to
perfection with cardamom and honey-
halva.

Tatte Bakery and Cafe |Address:

70 Charles Street, Boston, MA

Actual footage of Lia in her natural habitat: drinking

delicious coffee at Tatte in Boston.

After breakfast and coffee, head back

out to the street. Charles Street is
chock full of interesting and swoon-
worthy boutique shops that range from
home decor to glitzy trinkets to
independent clothing stores. Many
stores in the area are Boston or New
England themed, so you may have no
choice but to leave the city with
something lobster-branded, or tap into
your preppy side and buy a button-down
top. A few of my favorites are Black Ink,
Holiday Boutique, Rugg Road Paper, and
Good. Wander down the street and pop
into any shop that catches your fancy!

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···

At the intersection of Charles and

Beacon Streets you’ll find the Boston
Public Gardens, the first public botanical
garden in America and an excellent spot
to meander. Around late April, the
Gardens are bursting with color as tulips
are planted and the lawns are manicured
back to their springtime glory.

Spend some time people watching or

duck watching by the pond, and make
sure to see the Make Way for Ducklings
statues! Depending on the season, the
city of Boston dresses them up:
sometimes in bonnets, other times in
Tom Brady jerseys. And they’re every bit
as cute as they sound.

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···

Across from the Gardens is the Boston

Common, formerly a grazing meadow for
sheep. Come 11AM, food trucks begin to
park themselves on the Tremont Street
side of the park, the Cookie Monstah
among them. Their ice cream
sandwiches pair wonderfully with a day
full of walking! Which brings me to your
next activity…

The Massachusetts State House is one of the stops along

the Freedom Trail in Boston.

HISTORY TOUR OF
BOSTON
If the weather is nice, follow the red brick
road around Boston’s iconic landmarks.
This self-guided tour is called the
Freedom Trail. There are a number of
tours, like the Freedom Trail Tour, which
lasts 90 minutes and stops at 11 of the
trail’s 16 spots. You’ll get to hear the
story of the Boston Massacre at the
site, pause in the Old South Meeting
House, and admire the Massachusetts
State House while standing beside the
Massachusetts 54th Infantry
Memorial (Where are you Glory fans?).

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···

Freedom Trail | The guided tour

starts near the Park Street Station,
193 Tremont Street, Boston, Ma

Probably one of the silliest things you’ll

see in Boston is a man dressed in his
knickers and feathered cap sitting on a
park bench and scrolling through his
Instagram feed. He is most likely your
tour guide today! Plus, Boston is
probably one of the best cities in
America for feeling transported to
another era, and these guides fit right in
to this charming colonial imagery.

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···

When your tour wraps up at Faneuil Hall,

which is both incredibly famous and
incredibly touristy, stop and take a look,
but don’t eat here. Instead, walk across
the street to the Boston Public Market
and pick up a bag of Apple Cider Donuts
at Red’s Apple Farm for later. You may
even catch a street performer or two
assembling a crowd in the cobblestoned
square!

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 ···

LUNCH AT JAMES HOOK &

CO.
If Boston was a flavor, it would taste like
lobster rolls and clam chowder. James
Hook & Co. is a small shack that harkens
to coastal Maine, a little out of place in its
location next to big-time high-rises. The
inside, cramped with a few tables and
massive tanks for their lobsters and
seafood, feels like summer vacation.

Opt for one of their picnic tables outside,

and order the prescribed dosage of a
lobster roll with a cup of clam chowder.
A nice bag of Cape Cod chips and some
water will top it off nicely.

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···

James Hook & Co. | Address: 15-

17 Northern Avenue, Boston, MA

THE BOSTON TEA PARTY

MUSEUM AND
WATERFRONT
Just a six minute walk from James Hook
& Co. brings you into the Seaport
District, Boston’s fastest-growing
neighborhood. Still, they haven’t
forgotten their roots at the Boston Tea
Party Ships & Museum, where fully
restored 18th century ships bob in the
harbor and guests are led through an
interactive Boston Tea Party.

Learn more about these free-wheeling

Bostonians and rebels and partake in
“throwing tea overboard.” Then, cross
over to the Seaport side and meander
along the water to take in Boston’s
glorious skyline.

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···

Now, here are a couple of options for the

rest of the afternoon – or if the timing
works out right, you can do both!

Cycle along the Charles River Esplanade next to the

Boston Public Gardens and you’ll be participating in a
time-honored Boston tradition! This part of Boston is both
beautiful and historic.

AFTERNOON OPTION 1:
CYCLE ALONG THE
ESPLANADE
If the weather is nice, rent a bike and ride
along the scenic Charles River
Esplanade, neighboring the Public
Gardens. You can rent from Blue Bikes
(first download the app) or Urban
Adventours. At the latter company, you
make things totally romantic and rent a
tandem bike. If you would prefer a
guided tour you can book one here.

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···

The Esplanade is a 17-mile stretch of

pathways for bikers, joggers, and
sightseers, all looking for sailboats
dotting the horizon. Enjoy the breeze in
your face and the views of the river,
Cambridge just across the way (hi, MIT!),
and Boston’s iconic Back Bay
brownstones.

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···

AFTERNOON OPTION 2:
PRE-DINNER COMEDY
SHOW AT IMPROV ASYLUM
On Saturday nights at 5 PM, 7 PM, 10
PM, and 11:59 PM, nearby Improv
Asylum will work out the abs for a knee-
slapping good time. Improv Asylum
opened its doors as a Boston comedy
staple since 1998, and they now have
shows 7 days per week!

Improv Asylum | Address: 216

Hanover Street, Boston, MA

The North End neighborhood in Boston, Massachussetts

is known as Boston’s Little Italy, and it’s the best place to
get Italian food in town.

DINNER AT GIACOMO’S
Boston’s North End is famed for
remaining a largely Italian neighborhood
with family-owned restaurants and
specialty food shops galore. It
perpetually smells like pizza, and is
seriously adorable. Charm emanates
from every twisting street that deposits
you onto a similar lane of brick buildings
and 19th century exteriors, of flower
beds and neighbors meandering down
the street, of trucks unloading their
wines or bakery goods for the day.

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···

The North End is an overwhelm of

amazing places to eat. Everywhere you
look is another pizzeria, dimly-lit pasta
shop, or a varying form of carb and
sauce infused restaurant.

For dinner in the North End, head to

Giacomo’s. This tiny, no-frills Italian
restaurant serves up delicious, quick
Italian bites at reasonable prices.
Because the food is so amazing, it can
get crowded, so you may have to wait a
bit in the peak dinner times. Luckily, the
service is fast (one of the reasons why
it’s beloved by locals), and it’s walkable
from Charles Street, at ~30 minutes by
foot. Also, note that this place doesn’t
take credit or debit, so don’t forget your
ca$h money.

ADVERTISEMENT

···

Giacomo’s | Address: 355 Hanover

St, Boston, MA, USA

Although I’ve only scheduled one dinner

in the North End in this itinerary, you can
alternatively opt for an entire North End
walking & food tour (which is a 2-hour
morning tour). Taking this food tour will
give you a sample of all of the delicious
local food and desserts this
neighborhood has to offer!

Modern Pastry is the best place to get cannolis in the

North End, Boston’s Little Italy neighborhood. (Photo by
Tim Sackton on Flickr)

DESSERT AT MODERN
PASTRY
Boston’s best cannoli is not-so-secretly
homemade and sold at Modern Pastry.
Do NOT, I repeat, do NOT follow the trail
of people carrying Mike’s Pastry boxes,
because you will confuse your senses
and play a mental game of tug of war and
there’s no need to pause in your tracks
when another bakery’s logo is in sight.

ADVERTISEMENT

···

I am making a big deal of this because

the rivalry between Mike’s and Modern is
as old as the Sox and the Yankees, and
there’s one clear winner here. Modern is
a cash-only spot with rows upon rows of
lavishly frosted sweets and the smell of
freshly-baked pastries wafting through
the shop. Everything is made day-of…
SWOON. Opt for the chocolate chip
cannoli, a slice of one of their cakes,
and/or grab some butter cookies with
fig and raspberry fillings.

Modern Pastry | Address: 257

Hanover Street, Boston, MA

ADVERTISEMENT

···

GET SPOOKED ON A
GHOST TOUR
Does anyone else make it a point to go
searching for ghosts in new places? Your
best chance in Boston is on a tour with
Haunted Boston. This nighttime tour is
led by lantern light (cute AF) and dares
to cross into the peculiar, humorous, and
downright creepy phantoms that roam
the city.

ADVERTISEMENT

···

Tours are 90 minutes long. I took a tour

about eight years ago, and still freak
myself out when I think about the story
of Boston’s banshee! (I am also a
scaredy cat and not a good measure for
scare factor.) It’s only 90 minutes and
loads of fun!

Haunted Boston | Address: The

Boston Common at Boylston and
Tremont Streets, Boston, MA

READ THIS POST

10 Best Hikes in Southern

California (a Local's Guide)

TASTE DELICIOUS DRINKS

AT THE HAUNTED PARKER
BAR
If your spine is still chilling from the
night’s folklore, warm it up with a drink at
Parker Bar in the Omni Parker Hotel…
one of Boston’s most haunted hotels.
Walk over after the tour and cozy up in
the wood-paneled bar. You’ll have heard
stories earlier in the night about this
place, and why not keep the ghostly fun
going? A Champagne Cobbler will take
the edge off and help you sleep a little
better tonight.

ADVERTISEMENT

···

Parker Bar | Address: 60 School

Street, Boston, MA

Need another lobster roll during your 3 days in Boston?

We don’t blame you! Chow down at Yankee Lobster, next
door to Harpoon Brewery, for the perfect Boston lunch.

BOSTON ITINERARY: DAY

3
Your last day in Boston is all about food &
booze. You’ll visit a favorite Boston
coffee shop for breakfast and hit the
local brewery scene for beer & cider, all
while taking in waterfront views.

ADVERTISEMENT

···

COFFEE & PASTRIES AT

THINKING CUP
Time to coffee it up at a local mainstay!
It’s a 20 minute walk through bustling
downtown Boston to get to the Thinking
Cup. Thinking Cup serves Stumptown
coffee and other third wave faves along
with yummy breakfast treats. A blueberry
muffin, slice of their veggie quiche, or a
croissant are a must with any cup of
coffee.

ADVERTISEMENT

···

Thinking Cup | Address: 236

Hanover Street, Boston, MA

GO ALE OUT AT CRAFT

BREWERIES
Right now, Boston is resurging with craft
brews. Sam Adams is still alive and well,
but there are a couple of beer and cider
detours I’d recommend. You can take an
craft beer tour, or you can DIY your
afternoon of beer tasting.

Many brewing facilities and tasting

rooms are based in East Boston,
accessible by the silver line and about a
15 minute drive from one to the other,
but I recommend saving yourself the
confusion and taking a Lyft. Here are two
of my personal favorites to try:

ADVERTISEMENT
 ···

Harpoon Brewery: Harpoon’s

tasting room is pretty nifty. It’s a
long beer hall with floor-to-ceiling
windows that flood the space with
light, and the number of taps is
dizzying. For $5 you can tour the
brewery and learn about their
process, complete with samples of
their Harpoon and UFO beers.
When you’re finished, you can grab
yourself a pint and, get this,
ginormous pretzel of your flavor
choosing. The combo is life-size
here. Try their cinnamon pretzel
with icing, or parmesan pretzel with
marinara dipping sauce.
Harpoon Brewery | Address:
306 Northern Avenue, Boston,
MA
Downeast Cider House: Tours of
Downeast take place weekly from
Thursday to Sunday, they cost $9
and fill up quick. Important: If
you’re planning to visit the cider
house, you need to reserve a spot
at least four weeks in advance. It
is so worth it, you guys – the tour
includes history, awful jokes, and
tastings of their year-round blends
and seasonal favorites. From the
winter blend with cinnamon,
nutmeg, and oak, to tap-room
favorites like wild berry, inspired by
Maine, there is always something
new and delicious.
Downeast Cider House |
Address: 256 Marginal Street,
Boston, MA

ONE LAST LOBSTER ROLL

Before you hit the road, grab one last
lobster roll at Yankee Lobster, next door
to Harpoon Brewery and right on the
Boston waterfront. It’s the best way to
say goodbye to an amazing 3 days in
Boston!

ADVERTISEMENT

···

Yankee Lobster | Address: 300

Northern Ave, Boston, MA

3 days in Boston is definitely not enough to explore all of

this historic city, but it’s enough for a great introduction to
beautiful Boston. Original photo credit: “Boston Skyline”
by wuestenigel

SUMMARY: YOUR 3-DAY

BOSTON WEEKEND
ITINERARY
Day 1

Brunch at Neighborhoods Coffee &

Crepes | Address: 96 Peterborough
Street, Boston, MA
ADVERTISEMENT

···

···

Explore the Museum of Fine Arts |

Address: 465 Huntington Avenue,
Boston, MA
Explore the Isabella Stewart
Gardner Museum | Address: 25
Evans Way, Boston, MA
ADVERTISEMENT

···

Dinner at Tapestry | Address: 69

Kilmarnock Street, Boston, MA
Game/tour/walk around Fenway
Park | Address: 4 Yawkey Way,
Boston, MA 02215

Day 2

Breakfast at Tatte Bakery and Cafe |

Address: 70 Charles Street, Boston,
MA
Explore Charles Street, Beacon Hill,
and the Public Gardens
Freedom Trail Tour | Tour starts near
the Park Street Station, 193
Tremont Street, Boston, MA
James Hook & Co. | Address: 15-17
Northern Avenue, Boston, MA
Rent a bike and cycle the Charles
River Esplanade
See a comedy show at Improv
Asylum | Address: 216 Hanover
Street, Boston, MA
Dinner at Giacomo’s | Address: 355
Hanover St, Boston, MA 02113, USA
Dessert at Modern Pastry | Address:
257 Hanover Street, Boston, MA
Take a ghost tour with Haunted
Boston | The Boston Common at
Boylston and Tremont Streets,
Boston, MA
Haunted drinks at Parker Bar | 60
School Street, Boston, MA

Day 3

Coffee and pastries at Thinking Cup

| Address: 236 Hanover Street,
Boston, MA
ADVERTISEMENT

···

Brewery Tours at Harpoon Brewery |

Address: 306 Northern Avenue,
Boston, MA
Lobster Roll lunch at Yankee Lobster
| Address: 300 Northern Ave,
Boston, MA
ADVERTISEMENT

···

Brewery Tour at Downeast Cider

House | Address: 256 Marginal
Street, Boston, MA

By the way: We’ve compiled our

itinerary into a super handy, 1-page
downloadable! Print it out or load it up on
your phone so you can easily navigate
from place to place. Enter your email
below and we’ll send the itinerary right to
your inbox!

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WEEKEND IN
BOSTON
ITINERARY!
Enter your details below to get a
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About our Contributing

Writer: Hey there! I’m Lindsay,
a native Bostonian and new
New Yorker whose secret
weapon is my Bachelor’s
degree in writing (watch out,
us wordsmiths are reclaiming
the world!). I am a freelance
travel writer and full-time
proofreader and copywriter.
My money goes almost
exclusively to travel, Target,
books, and dessert!

Interested in sharing your travel tips or

giving our readers the local scoop on
your hometown? Contribute an article to
Practical Wanderlust! Check out our
contributor guidelines for more
information on how to pitch.

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···

Psst: Planning a trip to the East Coast?

Take a look at some of our other helpful
posts, or check out this guide to things
to do in Boston from our friends at New
England with Love and these East Coast
vacation spots on Diary of a Nomad.

17 Best Things to do in Boston,

Massachusetts in the Winter (A
Local’s Guide)
Self-Guided Walking Tour of Lower
Manhattan
The Ultimate Local’s Guide to
Washington, DC
10 Charming Places to Experience
Fall in New Hampshire

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OUR TOP TRAVEL TIPS &

RESOURCES
Here are our favorite travel tips &
resources for saving money and
planning travel logistics! For more tips,
check out our travel tips resource
page or our guide to planning a trip.
Booking Flights: To score flight
deals, search on Google Flights
or Kayak. Money-saving tips: fly
mid-week or on the weekend; fly
carry-on only on a budget airline;
and take red-eyes or early
morning flights.
Accommodations: We usually
stay in budget-friendly vacation
rentals, boutique hotels or private
rooms in hostels. We use
Booking.com to book hotels (we
love their flexible cancellation
policy) and Hostelworld to book
hostels (low deposit, easy
change/cancellation, and
excellent reviews). For vacation
rentals, we prefer to book using
VRBO because they've got lower
fees and better support than
Airbnb, and we're not fans of
Airbnb's unethical track record.
You can also book vacation
rentals on Expedia and
Hotels.com. We also use
TrustedHousesitters as both
hosts (for our home and our fur-
child) and travelers!
Travel Insurance: We always,
always, ALWAYS buy travel
insurance for international trips,
and we STRONGLY suggest it -
visit our Travel Insurance Guide
to find out why. We recommend
either World Nomads or
SafetyWing for international
travel insurance. SafetyWing is
one of the few policies that
covers Covid-19, and they have
excellent monthly policies that
are perfect for Digital Nomads
and long term travelers!
Travel Credit Card: We book all
of our trips on our favorite travel
credit card. Not only do we earn
cash back that we can spend on
more travel, but the card offers
fantastic travel perks like travel
insurance, trip delay and
cancellation coverage, lost
baggage reimbursement, and
rental car coverage, which helps
protect us on our travels. Learn
more here.
Vaccines & Meds: We use the
travel guides on the CDC
website to research
recommended medications and
vaccines for international trips.
We always recommend getting
every vaccine recommended by
the CDC! You can get them at
your primary care doctor's office
or a walk-in pharmacy.
Tours: We love booking guided
tours, especially food tours and
walking tours, to get a local's
perspective and a history lesson
while sight-seeing! We book our
tours using Viator and
GetYourGuide.
Transportation: We use
Rome2Rio to figure out how to
get from place to place, and book
local transportation online using
Bookaway wherever we can.
When we book a rental car, we
use Kayak to compare rental
companies and find the best
deal.
Luggage Storage: Whenever
 Luggage Storage: Whenever
we're checking out early or
taking advantage of a long
layover, we use LuggageHero to
safely store our luggage while
we're running around. Use the
code PRACTICALW for 2 hours of
free luggage storage on us.
VPN Service: A VPN keeps your
digital information (like website
login details, bank info, etc) safe,
even when you're connected to
an unsecured network while
traveling. Plus, it lets you use
Netflix & other streaming sites
abroad! We use NordVPN. Use
the code WANDERLUSTPROMO
when you sign up!
What to Pack: Here are the
travel essentials that we bring on
every trip. We also have packing
lists for hot weather, cold
weather, and many more. Take a
look at all of our packing guides!

BOSTON CITY TRIPS

ITINERARIES MASSACHUSETTS

THE EAST COAST USA CITY

W E E K E N D G E TA W AY

Written by Contributor
This blog post was created by a
contributing writer. Are you a
blogger, writer, or just an avid
traveler with lots of travel tips to
share? Take a look at our
Contributor Guidelines and pitch
us your idea!

COMMENTS

ABIGAIL REAGAN SAYS

S E P T E M B E R 3 0, 2 0 2 0 AT 1 1 : 3 7 A M

I’m also from Boston! Loved reading about my

hometown from your perspective ♡

R E P LY

ANGELA TAYLOR SAYS

A P R I L 2 7, 2 0 2 0 AT 3 : 4 5 A M

Boston is an amazing city to visit. I am

planning to go to Boston for a trip for that I
have to prepare an itinerary for a systemic
trip. But I don’t think now I have to put much
efforts and time in this. After reading this blog
my work becomes easy. Thanks for sharing!

R E P LY

VERTOE SAYS
A P R I L 2 0, 2 0 2 0 AT 1 0 : 1 0 P M

Amazing blog! People who are planning a stay

for 3 days in Boston must enjoy the hop-on
hop-off sightseeing trolley, a Fenway park
tour, skywalk observatory, old state house,
and the New England Aquarium. These are
some of the best attractions which one
cannot miss in Boston.

R E P LY

MARY BETH SAYS

M A R C H 3 0, 2 0 2 0 AT 7 : 2 7 A M

Great post. Springtime is definitely ideal to

visit Boston because of the lack of college
students, although October can be a fun time
to check out the Salem shenanigans. Boston
is “America’s Walking City” so the Freedom
Trial is definitely an on-point suggestion for
those who want natural scenery, history,
culture AND to burn some calories. It’s also
great for the “navigationally challenged”
people like me because with the red brick
road, it’s impossible to get lost.
For affordable hotels, I would highly
recommend the YOTEL in the Seaport area.

R E P LY

NEW YORK CENTRAL SAYS

JA N UA RY 8, 2 0 2 0 AT 6 : 3 7 A M

Been to Boston a number of times, and would

like to recommend the Boston Museum of
Science and the New England Aquarium as
alternatives if your interests run more to
science than art. :). The NEAQ’s Giant Ocean
Tank is a truly impressive sight, and they run
whale watches from the pier at various times
of the year.

R E P LY

LIA GARCIA SAYS

JA N UA RY 8, 2 0 2 0 AT 1 1 : 2 4 A M

Fantastic recommendations, thank you!

R E P LY

WALT YOUNGLOVE SAYS

S E P T E M B E R 1 4, 2 0 1 9 AT 5 : 3 8 P M

Loved the idea of taking in a Red Sox Game.

They will be in town when we go in June. Any
advice on when individual tickets for the 2020
season will go on sale?

R E P LY

LIA GARCIA SAYS

JA N UA RY 2 4, 2 0 2 0 AT 2 : 4 5 P M

You know, I just am not sure! You’d have to

Google that one.

R E P LY

MELANIE PEREZ SAYS

J U N E 8, 2 0 1 9 AT 1 0 : 5 2 A M

Loved this post! Thank you for giving an

inside scoop on the best parts of Boston – I’m
visiting mid July and was thinking of bringing
along my dog with me. Do you see a lot of
dogs around Boston? Or is it more of a people
city
Thank you again!

R E P LY

LIA GARCIA SAYS

J U N E 1 2 , 2 0 1 9 AT 7 : 3 1 A M

Honestly it’s not something I pay very

much attention to since we don’t have a
dog ourselves, but there are absolutely
plenty of dogs in Boston

R E P LY

APARNA SANJAY SAYS

M AY 7, 2 0 1 9 AT 9 : 4 8 A M

This is such a great post. We are in Boston in

late July and will definitely be following this
itinerary. Also, I wanted to thank you for your
wonderful walking tour of Lima post which I
used when we were in Peru in early April. We
couldn’t finish the entire suggested route as it
was a super hot day but managed to get
some good sights and click some good
photos!

R E P LY

LIA GARCIA SAYS

M AY 8, 2 0 1 9 AT 1 0 : 1 1 A M

Oh fantastic! I’m so glad to hear that you

liked the Lima walking tour Have a
great time in Boston!

R E P LY

HARMONY, MOMMA TO GO SAYS

A P R I L 1 3, 2 0 1 9 AT 5 : 0 1 A M

My husband is from boston – and went to BC!

We need to get up there this summer – esp
since my son is learning so much about
American History this year. I love the North
End, and all the parks. Walking around for
sure. Its an easy city to just walk!

R E P LY

KATIE DIEDERICHS SAYS

A P R I L 1 2 , 2 0 1 9 AT 1 1 : 1 8 P M

Boston has been in our minds lately. This blog

post has given us the push we needed to
finally decide on going through with it. We
plan on following this amazing itinerary,
however, my niece may be coming on the trip
with us. Are there any child-friendly places,
you would suggest we go to?

R E P LY

HEATHER ALFANO SAYS

M AY 1 1, 2 0 2 0 AT 2 : 2 2 P M

Hi there! If there’s nice weather, Boston

has tons of stuff for kids! You can see it
just by how many playgrounds there are
around the city. The Museum of Science is
a wonderland for kids’ curiosity (and
people of all ages), and so is Boston
Public Library’s central branch in Copley
Square. The modern side of BPL Central is
particularly engaging for kids. Depending
on your niece’s age/interests, she may
enjoy the Boston Ballet (like The
Nutcracker) the top of the Prudential
Center observatory, and performances at
the Boston Opera house (I’m thinking a
musical). Also, pro-tip: the local restaurant
chain Bertucci’s is great for kids. They
give kids dough to play with, and my
rambunctious four siblings and I always
loved going And if you’re able to do a
day trip, Canobie Lake Park in Salem, NH
is an hour’s drive away and is a a sweet,
family-run amusement park with plenty to
do for people of all ages. Hope some of
this is helpful!

R E P LY

LIA GARCIA SAYS

M AY 1 1, 2 0 2 0 AT 2 : 4 6 P M

These tips are so helpful! Thank you,

Heather!

R E P LY

APRIL SAYS
A P R I L 1 2 , 2 0 1 9 AT 8 : 0 4 P M

Sadly I’ve only ever done Boston as a day trip

from NYC. And both times I did the Freedom
Trail (it was 10 years apart) as I’m a history
junkie. And, I can’t leave without stopping in
Little Italy for cannoli from Mike’s Pastry (will
need to try Modern’s next time). I realy need
to go back so I can expand out further. Boston
looks so colorful!

R E P LY

KAY SAYS
A P R I L 1 2 , 2 0 1 9 AT 7 : 1 6 P M

BOSTON IS ONE OF MY FAVORITE CITIES IN

THE UNITED STATES!!! You got all the best
spots on here!

R E P LY

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In 2016 we quit our jobs, put our stuff in

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