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Everything to Put on Your Boston Itinerary

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The best Boston itinerary, by travel blogger What The Fab

Sharing everything you need to put on your Boston itinerary today! Boston is such a cool city. My sister and my best friend have lived there at one point in time, so I’ve had plenty of opportunities to visit and explore.

The capital of Massachusetts, this old city has a ton of history in its streets—from its centuries-old buildings to its historic eateries. It’s the epicenter of the history of the United States and home to key figures in the American Revolution.

And even if you’re not a history buff, there’s still a ton of things to do in Boston! Think rooftop bars, aquariums, contemporary art, and food.

If places like New York City are a little overwhelming for you, I think you’ll love Boston. It has a fun city vibe, but in a more relaxed, low-key way.

I’ve put together a bunch of awesome stuff to add to your Boston itinerary to give you some inspiration and get you pumped for your trip. So let’s do it!

Everything to Put on Your Boston Itinerary

The best Boston itinerary, by Travel Blogger What The Fab

Freedom Trail

You may have heard of the Freedom Trail—and there’s a good reason for that. Spanning 2.5 miles through Downtown Boston, this path through the city passes by historic sights that paint a picture of American Independence.

Starting out at Boston Common, if you want to truly understand the background and significance of the sights (and properly soak up all the information), it will probably take you a whole day to meander the route.

Boston Common is worth its own trip, to be honest. It’s actually the oldest public park in the United States, and there’s a Visitor Center where you can learn more about its history.

From there, it’s on to Park St. Subway Station—another first for the U.S.! It opened up in 1897. The Freedom Trail then continues through a total of 14 further official sites, including the Massachusetts State House, among others.

Basically, it’s a super interesting way to see the city. Of course, you can take yourself on a free self-guided walking tour (there are plenty of maps and online guides), but you could also opt for a bus tour.

Old State House

The current Massachusetts State House is definitely a sight to see in Boston, but for even more history, you should head to the Old State House.

The clue’s in the name; this is actually the oldest public building in the whole of Boston! Dating back to 1713, it was a meeting place and the center of politics in the colonies, but most importantly, it’s here where the Declaration of Independence was read (from the balcony, to be exact).

Just below is where the Boston Massacre took place.

Visiting the Old State House is a great option if you don’t have time (or the interest, lol) to walk the entire Freedom Trail. You get a whole lot of insight in one place and get to feel a concentrated sense of striving for independence.

New England Aquarium

If you happen to be in Boston with children (or even without kids) and you’re looking for fun things to do, I would recommend swinging by the New England Aquarium.

This big center is home to more than 20,000 marine animals. The main draw here is the huge ocean tank, complete with its very own coral reef.

The coolest thing about the New England Aquarium is the spiral walkway that surrounds the main tank. But the cutest part has to be the penguin exhibit. Here, you’ll find different types of penguins, including the adorable rockhopper penguins (you know, with the funky eyebrows). When we visited with my friend and her little boy, he was so in love with the penguins he kept asking if they could adopt one and keep it in their bathtub. 🤣 It was so sweet.

Located on the waterfront in Downtown Boston—on the Central Wharf—visiting the New England Aquarium is a fun day out and also a great option if it’s raining.

The best Boston itinerary, by travel blogger What The Fab

Boston Public Garden

Definitely put a stroll through Boston Public Garden on your itinerary.

This Victorian-era public park, located next to Boston Common, was established in 1837, and it’s the first public botanic garden in the United States.

Flowers, pretty walkways, and statues are strewn throughout. Walking through here on a sunny summer day is pretty idyllic.

One of the statues here is super cute and you might recognize it from your childhood. It’s the “Make Way for Ducklings” statue based on the famous 1941 children’s book by Robert McCloskey. Very nostalgic to see!

If the weather’s good, you should totally take a ride on one of the swan boats! Not only are they fun, but they’re also historic—they’ve been in action since 1877.

The best Boston itinerary, by travel blogger What The Fab

Isabella Stewart Gardner Museum

Pretty much like a palace, the Isabella Stewart Gardner Museum actually started life as a 15th-century Venetian style palace for an art collector and philanthropist Isabella Stewart Gardner.

She started collecting art when she has left a large inheritance and opened a museum in 1903.

Don’t you wish you could have attended the opening party?? The guests dined on champagne and donuts to a backdrop of music by the Boston Symphony Orchestra. Sounds like a great night!

One strange fact about this museum is that they had $500 million worth of artwork stolen in 1990—a case that remains unsolved.

Art and architecture fans should definitely check this place out (it’s a good one for Insta, people).

The best Boston itinerary, by travel blogger What The Fab

Fenway Park

Batter up! Fenway Park is home to the Boston Red Sox—one of the most famous baseball stadiums there is. First opened in 1912, it’s the oldest Major League Baseball stadium.

Needless to say, if you’re a fan of the Boston Red Sox—or if you just love baseball—taking a Fenway Park tour should be very high up on your Boston itinerary.

Head out on ballpark tours where you can learn about the legends that have played there from experienced guides. History, sports, and even the chance to sit on the prime seats at the leftfield wall— aka the Green Monster—it’s all here.

And if you’re lucky, you might just be able to score tickets for a game. A must-do if baseball is your jam!

Harpoon Brewery

Harpoon Brewery is a super popular brewery, especially for beer nerds. They not only puts on tours (hosted hourly for $5) where you can learn about the beer-making process—and sample a few cold ones for yourself, of course—but it also has a German-style beer hall.

Settle in at the super-long wooden bar and begin an odyssey of beer-tasting. There are 20 different taps to choose from!

My tip is to grab a pretzel (ok, maybe a few pretzels!) because they’re all sorts of amazing and go very nicely with a beer or two.

There’s a great vibe here. It’s not super touristy at all, and is a pretty local place to come for music, merriment, and munching on hearty food. If you find yourself in Boston on St Patrick’s Day, for example, this is an awesome place to come.

Boston itinerary, by Travel Blogger What The Fab

Eat seafood

Foodies should already know that Boston is a prime location for seafood. There are a ton of lobster shacks and seafood joints where you can dive into creamy clam chowder or freshly-shucked oysters. Yum!

Not all places are equal, obviously, so for one of the most famous places in town to chow down on seafood, head to Union Oyster House. Sure, it may be touristy, but that doesn’t mean it’s not worth it.

Founded way back in 1826, this well-established eatery is actually the oldest continuously operating restaurant in the whole country. That’s one reason to visit. But the food is another.

The oysters Rockefeller, for example, and the lobster pots are amazing. The most coveted seat in the house is the “Kennedy Booth.” Yep, you guessed it—it was JFK’s favorite seat in the restaurant.

For something a bit different, go to Porto for a Mediterranean twist, or Neptune Oyster for fresh and delicious (be warned: there’s always a line outside).

Boston Common

I said earlier that Boston Common was worth a visit all by itself—even if you’re not planning on walking the Freedom Trail.

It’s basically the more carefree sibling park to Boston Public Garden. This is the place where Bostonites and visitors head to for relaxing and to meet friends on warm summer days.

My personal favorite place is the Boston Common during the fall (it’s beautiful). But then again, in winter, there’s an ice skating rink here.

Bring a book, find a bench and read, or simply people-watch as you enjoy some time out from sightseeing.

Watch out for the squirrels though—they may act cute, but you shouldn’t feed them. Some people claim they’re “almost domesticated,” but they’re still wild animals!

Blue Hills Reservation

If you’re looking to get out in nature, then you should consider going to the Blue Hills Reservation.

Literally travel just a few minutes from Downtown Boston by car and you’ll be in this huge green oasis of nature. Over 7,000 acres of nature, to be more exact.

The park’s varied landscape is ideal for hikers, mountain bikers, and even skiers (at the right time of year, of course).

There are 125 miles of trails that wind through the park, some gentle and pretty easy, some more challenging. You can actually climb to the top of the Blue Hills Mountain Range, which means you’ll get an incredible panoramic view of Boston’s skyline.

It’s a pretty steep way up though, so be careful and pack snacks and water!

For something easier, the Wolcott and Border Path is a woodland lane that runs from the reservation headquarters through pines and hemlock trees.

Faneuil Hall Market Place

Opening in 1743, Faneuil Hall Marketplace may be historic and have some pretty neat stories—for example, Samuel Adams used to make speeches here—but it’s also about the present-day vibe.

Stores, restaurants, and cafes now occupy the historic building, making for a unique local spot to hang out, watch the world go by, grab something to eat, or pick up some special gifts and souvenirs.

It’s charming, in a word. There are cobblestone promenades where you can be wowed by street performers and window shop for hours.

If you want some history infused with your visit, there are local guides posted around that you can chat to, and ask about the goings-on that have happened over its 270-year spot. On the 4th floor, there’s even a military museum, if that’s your thing.

A fun mall-with-history setting where you can sip a coffee in the morning and grab an alcoholic beverage after dark, a trip to Faneuil Hall Marketplace is totally one of the best things to do in Boston—one of my favorites, actually!

The Rose Kennedy Greenway

A park with a difference, the Rose Kennedy Greenway—or simply “the Greenway”—is a ribbon-like green space that runs through the city, connecting several Downtown Boston neighborhoods.

The Greenway is actually the result of an expressway being demolished. Rather than building over the vacant gap left by that event, the city decided to create this urban green space instead.

Today, it’s filled with landscaped gardens, promenades, fountains, artwork, and plazas to hang out in. More than simply just a park, however, this makes for a great way to get from A to B via the scenic route.

It’s also a great spot for any weary traveler who needs to take a breather from pavement pounding to regroup and relax for a minute.

There are even swing seats to chill in! And sometimes, there are food festivals going on here, making it even more of a worthwhile place to visit.

What’s here now couldn’t be more different from the expressway that was here before—and I absolutely love it. A cool idea that more cities should get on board with.

Boston itinerary, by Travel Blogger What The Fab

The Museum of Fine Arts Boston

Art fans listen up! The Museum of Fine Arts Boston has a super wide-ranging art collection, all the way from prehistoric to the modern-day.

The building itself is this huge, palatial, Neo-classical building that definitely deserves some time outside admiring the exteriors.

The museum actually contains more than 450,000 works of art. If you want big names, they’re here too—there are van Goghs, Rembrandts, and Monets. But there are also mummies, ceramics, and sculptures from the Roman Empire, Egypt, and Greece, and artifacts from the African continent.

The fashion exhibits are pretty cool, too! You get to see gorgeous designer pieces from throughout the 20th century, plus some iconic fashion photography on as well.

Basically, if you like art, history, fashion, or any combination of those three—or if you’re just visiting Boston for a few days—then I totally recommend paying a visit to the beautiful pieces and exhibits here.

Newbury Street

Located in the Back Bay area, which runs from Boston Public Garden to Brookline Avenue, Newbury Street is a super chic area for shopping!

Here, you’ll find stylish salons and boutiques set along the leafy, tree-lined avenue itself, with a few cafes and eateries along the way for those well needed (and very elegant) pitstops.

This trendy shopping district isn’t just about high-end stores though; there are some smaller, more quirky establishments that are well worth a window shop.

Of course, you could drop some serious cash if you wanted to, but Newbury Street is honestly nice enough for a wander—particularly in spring and summer when the sun’s out. That also happens to be the best time of year for sitting outside cafes sipping on your drink of choice!

One particularly cool place is Trident Books & Cafe. I highly recommend their ALL DAY breakfast menu—totally necessary after a late night!

SoWa Open Market

SoWa (South of Washington) is Boston’s creative art and design district—a favorite of hipsters and creative types. While it’s worth a wander any time of year if you’re into craft coffee, repurposed buildings, and street art, there is a particularly good time to find yourself in SoWa.

Every Sunday between May and October, SoWa comes alive with the Open Market—Boston’s largest extravaganza of all things music, art, and food.

Thousands of people make their way to the district to sample street food, check out the latest work from local designers, and pick up produce at the farmers market.

When you’re done shopping and browsing, it’s time to head to the beer garden. Each Sunday sees a different local brewery takes over the beer garden, serving up their take on beer—complete with snacks, of course. Throw in some live music and you’ve got a winner; a perfect Sunday afternoon in Boston!

The Paul Revere House

The Paul Revere House is on the Freedom Trail, but if your Boston itinerary only affords you enough time for a short trip, then you should take a trip to this landmark.

This 17th-century house is the oldest building in Downtown Boston and one of the oldest wooden dwellings of its kind in any American city. Pretty cool!

But if you know your history, you’ll already be aware that Paul Revere is also a famous Bostonite and patriot of the American Revolution. He lived in what is now called the Paul Revere House from 1770 to 1800.

Today, you can take tours of his home (entry $5), learn about life in the 18th century, see artifacts from way back when, and learn the story of his famous Midnight Ride.

Guides dressed in period clothing will take you on a tour (in character, too) for a bit more of a fun approach to history that isn’t just signs.

The best Boston itinerary, by Travel Blogger What The Fab

Skywalk Observatory

Want to see Boston from up high? Then head to the Prudential Center—the second-tallest building in Boston.

Once you’re there, take the elevator to the 50th floor. This where you’ll find the Skywalk Observatory, complete with panoramic views of the city skyline and further afield. Some days, when it’s clear, you can see as far as New Hampshire!

My favorite time for this sort of thing is sunset. There’s nothing quite like watching as evening falls on the city and the buildings start lighting up. Everyone else thinks so, too—it can get pretty busy around sunset!

It closes at 10 pm, so if you want to miss the crowds as the sun goes down, you can still go up later to see the glittering lights of the city. There are also places to grab a seat, exhibits, and interactive displays about the past of Boston.

If you want to avoid the crowds completely, is to go early in the morning.

Whatever time you go, it’s a very cool thing to do in Boston and makes for an awesome way to wrap up—or start—your time in the city. The views are incredible!

Go for rooftop drinks

If views from up high are your thing and you want a more lingering and interactive experience than the Skywalk Observatory, there’ll be nothing better for you than pairing a glittering view of the city with a cocktail in hand.

There are actually quite a few places dotted around the city where you can get a view of nocturnal Boston with added drinks—from upscale and elegant to more affordable fun.

A selection of them is hotel bars. There’s Sky Lounge at YOTEL Boston, with insane skyscraper views in a chic setting, while Colonnade Hotel has a notoriously hip rooftop bar with prices to match, and Lookout Rooftop and Bar—atop the Envoy Hotel—is a sparkly setting (there can be a wait).

Less high-end and a bit more lively, Dorchester Brewing Co. has outdoor terraces and amazing BBQ for a more down-to-earth in-the-sky experience. There’s also Sam Adams Faneuil Hall Taproom, complete with a rooftop deck and great views.

Take your pick—I’m sure you’ll find the best rooftop bar in Boston for you!

Everything to put on your Boston itinerary, by Travel Blogger What The Fab

Boston Public Library

Ok, so visiting a library may not seem like the coolest thing to do in Boston, but trust me, you should consider stopping by the Boston Public Library.

It may not be for everybody, you know, just going into a library, but if you want somewhere to admire architecture—or if you want to fill your Insta with some cool interior shots of the library—then you should make a a stop here.

Though it’s free to go in by yourself and check out the much-loved Reading Room (and take some photos, too), you may be better off with a guide. The library offers free guided tours, where you’ll be filled in on the Renaissance style architecture, murals by John Singer Sargent, and the general history of the building.

Tip: The library also has a beautiful cloistered courtyard, complete with fountain, where you can take some time out—maybe with a book if you feel like it.

But remember—ssshhh!

Everything to put on your Boston itinerary, by Travel Blogger What The Fab

Harvard University

A few miles from Downtown Boston is the world-famous Harvard University. It’s the oldest of its kind in the United States and rightly holds an iconic place in the country’s higher education scene.

Can you believe it was actually established back in 1636?? That’s old af, for the U.S.

The student-led tours of Harvard University are pretty fun. The daily, 70-minute guided tour will walk you through the historic campus, where you can check out the Widener Library, the Memorial Hall, and the John Harvard statue.

Everything to put on your Boston itinerary, by Travel Blogger What The Fab

Hit the Beach

Summer totally means beaches.

And lucky for you, Boston has a selection of beaches—some within the city limits, others just a short drive away.

Nantasket Beach is one of the best beaches near Boston. Just outside the city, it takes 30 minutes to get there, and there’s a Victorian, seaside feel to it. It has a classic New England vibe, with sandy beaches, taffy shops, and a family-friendly atmosphere.

Another option is Crane Beach. This very pretty public beach is great for a stroll among its coastal dunes—more of a natural, windblown feel than one to layout on.

There’s also Revere Beach. Just five miles from Boston, it’s actually the oldest public beach in the United States. There’s a boulevard, restaurants, and amusements along its three-mile-long crescent of sand. It’s pretty fun here!

Everything to put on your Boston itinerary, by travel blogger What The Fab

Go whale watching

If the beach isn’t your sort of coastal jam, then maybe spotting whales is.

Best seen from April to October, Boston is a great jumping-off point to go see whales in their natural habitat.

Most tours will set sail to the 842-square-mile Stellwagen Bank Marine Sanctuary, which is a feeding ground for an array of marine life, particularly whales.

You may be lucky enough to have the chance to see several different species of whales, including Minkes, Finbacks, and Humpbacks.

There are a number of different companies that will be able to cater to your whale watching needs, or you could take a whale watching tour from the New England Aquarium in town.

Institute of Contemporary Art

The Institute for Contemporary Art is a striking building. It’s all square, sharp angles, and glass, making it one that you’re going to want to snap a zillion photos of before you even step inside! Super cool.

Inside, it’s all about the art, of course.

Edvard Munch, Roy Lichtenstein, and Andy Warhol (to name just a few) have all had some of their iconic works displayed here. There are usually contemporary, relevant artists being shown, sometimes in themed exhibits.

It’s a serene space to take it all in. There’s even a viewing deck on the 4th floor that looks out over the water, so you can reflect upon all the awesome art you’re admiring. It’s a really nice space.

The gallery has sparked a bit of cool development in the surrounding area, with stores and places you can stop by to have a drink.


For late night eating and a lively vibe at any time of day, go to Boston’s Chinatown!

It’s the beating heart of Downtown Boston, open—it seems—24 hours to anybody with an empty stomach who needs it full of delicious food STAT!

As you’d expect, there are a TON of places to eat in Boston’s Chinatown; you will never be without something to eat. With hidden areas to explore, as well as history to learn about, this district makes for just more than an enclave of eating (though I’d say that’s pretty important, too).

First populated by Chinese migrants in the 1890s, this is actually the third-largest Chinatown in the United States.

Even if you’ve only got one day, Boston is such a cool place to visit. There are so many awesome things to do in this city listed here that you won’t have any trouble finding a few things to do in Boston that are perfect for you.

Go ahead and tag me (@wtfab) in your Insta stories and pics—I wanna see what you get up to in Boston!

Planning a trip to Boston? Be sure to check out my other Boston content here.

Boston Airbnbs
Boston Travel Diary
Photos from Boston


How many days do you need in Boston?

It is recommended to spend at least 3 to 4 days in Boston to really explore what the city has to offer.

What is the best time to visit Boston?

The best time to visit Boston is spring or fall since the weather will be at its best.

Is Boston safe for tourists?

Yes, Boston is overall a very safe place for tourists, however, it is always important to be aware of your surroundings. Avoid areas that make you feel uncomfortable.

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