3 Days in Boston: The Ultimate Weekend Itinerary for Boston, Massachusetts

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!

Psst: Planning a trip to Boston? Here are some other posts that you might find helpful:

• 17 Best Things to do in Boston, Massachusetts in the Winter (A 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 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!

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.

You know all that David Ortiz this is our f***in city! rallying? It’s not just for show.

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.

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.

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.

When to Visit Boston

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

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).

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!

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.

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!

• 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.

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!

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!

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.

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.

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!

Now that you’ve got all the tips you need, without further ado, here’s your ultimate weekend guide to Boston!

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.

It’s hard to pin down the best of Boston in three days but, hey, you’ll just have to come back!

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!

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.

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?!

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

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.

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!

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

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.

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.

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.

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.

• 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.

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.

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.

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.

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!

• 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.

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

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!

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.

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…

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?).

• 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.

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!

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.

• 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.

Now, here are a couple of options for the rest of the afternoon – or if the timing works out right, you can do both!

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.

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.

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

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.

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.

• 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!

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.

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

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.

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

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.

• Parker Bar | Address: 60 School Street, Boston, MA

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.

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.

• 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:

• 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!

• Yankee Lobster | Address: 300 Northern Ave, Boston, MA

Summary: Your 3-Day Boston Weekend Itinerary

Day 1

• Brunch at Neighborhoods Coffee & Crepes | Address: 96 Peterborough Street, Boston, MA
• Explore the Museum of Fine Arts | Address: 465 Huntington Avenue, Boston, MA
• Explore the Isabella Stewart Gardner Museum | Address: 25 Evans Way, Boston, MA
• 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
• Brewery Tours at Harpoon Brewery | Address: 306 Northern Avenue, Boston, MA
• Lobster Roll lunch at Yankee Lobster | Address: 300 Northern Ave, Boston, MA
• 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!

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.

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.

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