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Boston, Massachusetts: a buzzing gem of a city that boasts nothing but charm, a place known for its iconic Fenway Park, baseball and fall leaf color. As somewhere with a rich, colorful history, a vibrant up-and-coming food scene and so much more, there’s something to suit the tastes of every single visitor who steps off the plane, train, or just off their doorstep.
Though it is a small city, it’s almost impossible to know where to begin without the help of a trusty Boston travel blog. Aside from the tourist hotspots that are more than worth a visit, there are hidden gems here nestled between every red brick and down every street — gems you might not know about if it wasn’t for a local’s travel guide.
In this off-the-beaten-track Boston travel guide, you’ll find out all about which sights you should add to (and then promptly tick off) your list, which hotels you should stay in to feel the true magic of the city, and of course, which eateries you’ll want to spend a morning, afternoon, evening in — whether you’re on your own, here for a romantic break or with your family.
Wherever you decide to go, you’ll always have Old Town Trolley Boston by your side to help you from one destination to the next. Come rain or shine, turn to these trusty Boston travel tips backed by none other than Boston locals themselves. Excited? You will be.
Popular Neighborhoods to Discover in Boston
A local’s guide to visiting Boston doesn’t just cover the tourist hubs we all know and love but also lesser known highlights such as the Freedom Trail, one of the most exciting stops on an Old Town Trolley Boston tour — and for good reason. Dive into the Revolutionary history of Boston on this 2.5-mile walk, which winds through some of the most important historical sites in the city.
Taking you past 16 important sites from the American Revolutionary War, it’s one of those Boston travel tips you’ll be passing along from one interested listener to the next. Starting on Boston Common, you’ll learn all about various cemeteries, battlegrounds and historic churches before finishing at the USS Constitution and Bunker Hill. Depending on how much time you have planned in Boston, you’ll either want to have a quick walk or, as many a local’s travel guide will suggest, take your time learning about each checkpoint as part of a longer trip.
The next gem in this Boston travel guide is the ever-famous Fenway. Although one of the city’s most popular attractions, it holds a heartfelt spot on any local’s guide to visiting Boston thanks to its crowning jewel: Fenway Park. This buzzing neighborhood isn’t just known for its sporting ground, though; both baseball enthusiasts and culture lovers will find a home in this vibrant and welcoming area.
Known for its youthful feel, there are 12 of Boston’s 100 colleges located right here, as well as the Museum of Fine Arts and Symphony Hall. This lends a warm, academic feel to Fenway, giving way to colorful bars and clubs dotted along Landsdowne Street. An ideal spot for groups of friends and solo travelers, take one of our top Boston travel tips and visit the area from sundown onward to get the most out of Fenway.
Named for the small streets and picturesque waterfront location, Little Italy is one of Boston’s most charming spots. Defined by some of the city’s oldest buildings, no local’s guide to visiting Boston is complete without this instant classic. Take time exploring each street in this 1-square mile stretch and sample some of the local Italian delights from the most authentic Italian eateries in Boston. From budget to high-end, this local’s travel guide recommends trying out at least a few places to get the true taste of Italy before dipping into one of many shops and exploring the local historical sites.
No city break is perfect without seeing it from a completely new perspective. In this case, Beacon Hill is our number one go-to for capturing Boston from up high. Known for being home to the Massachusetts State House, this historic neighborhood is a feature in this Boston travel guide for only the best reasons.
Aside from its pleasing red brick streets and an unbeatable view of the Boston skyline, it’s somewhere visitors and locals alike can visit when they want to take a step back into the past. Magical and at times opulent, every local’s guide to visiting Boston will name this as a memorable stop on every Old Town Trolley Boston tour.
Every Boston travel guide will name one neighborhood when recommending the best place to visit in Boston. Known for being a place of stunning contrast, you’ll find modern, glittery skyscrapers alongside beautiful brownstone buildings, cozy indoor spaces and lush green parks. Sound tempting? You’ll be agreeing with every local’s travel guide in never wanting to leave.
Starting as a marshy riverside spot, a community was built into one of the most affluent waterfront areas in the city — one which feels more Boston than anywhere else. Coined as a place to wander, take more time than you need to explore each avenue: one of the Boston travel tips we can’t recommend enough.
Non-Touristy Things to Do in Boston
Kelleher Rose Garden – While Boston’s tourist spots are still well-loved local institutions, its hidden gems are where its charm lies — many of which Old Town Trolley Boston stops at. First on this local’s travel guide is Kelleher Rose Garden. Located just behind the Back Bay Fens are sprawling, pristinely kept flower beds filled with over 200 varieties of roses. When in bloom, this picturesque slice of calm provides an oasis away from the hustle and bustle of the city and offers a vibrant pop of color among the urban cityscape. Escape here whenever you want to reconnect with nature, and you’ll find it impossible to be torn away.
SoWa Open Market – Boston is nothing if not versatile. A haven for history buffs and food lovers, keen crafters can also find a home here with SoWa Open Market. Popping up on every local’s guide to visiting Boston, it’s a hub for creative types and foodies. Housing over 200 makers, there are art studios, galleries, food trucks, ceramics stalls, local farm produce sellers, and even vintage clothing pop-ups. A place to get lost in, and only in the best way, fill an entire afternoon picking up keepsakes from your trip and trying some of the best local delicacies around. Visit during summer on a Sunday to catch this gem in full bloom.
Brattle Book Shop – Book lovers rejoice: This is one of the Boston travel tips you won’t forget in a hurry. One of the oldest and largest used book stores in the whole of the United States, Brattle Book Shop is every avid reader’s heaven. Find every genre under the sun here, from your most reliable chick lit to classical literature and volumes of beautiful poetry. With prices starting from as little as $1, you may need to bring an extra bag to fill with all the treasures you find. Or better yet, come with your own, and Brattle Book Shop will buy them from you, giving you more to spend on whatever you find here. Rare book enthusiasts will also delight, as there are also often rare editions on sale.
Harvard Film Archive – In this Boston travel guide, you’ll very quickly learn that Harvard is not just for students. The Harvard Film Archive is open to everyone — especially those who love their cinema. Home to over 36,000 movies of all genres, there’s no better place to come to satisfy your creative taste buds. Explore the archives, or visit the HFA every single day of the week to catch one of their showings. With so many films on offer, you’re likely to find at least one you’d love to watch in their ornate, state-of-the-art cinema. When you’re done, you’ll feel more than ready to tackle the next stop on your Old Town Trolley Boston adventure.
Best Areas to Stay in Boston
A favorite neighborhood among locals and visitors alike, Back Bay represents the best of Boston in its diverse streets. Known for its brownstones and modern skyscrapers, it rests on the Charles River and boasts some of the richest cultural and historical sites in Boston — perfect for first-timers who want to take in as much of Boston’s history as they can.
Offering a more suburban feel, South End is an artsy part of the city that makes it onto many a local’s guide to visiting Boston. With cozy bars, galleries and places to eat, there’s an international feel here you won’t get in other parts of the city. Alongside traditional Victorian-inspired housing and sprawling parks, there’s accommodation here to suit every kind of budget imaginable.
One of the most popular parts of Boston to stay, there is something here every kind of visitor will love — especially families. Spreading from the northernmost part of the city up to the picturesque waterfront, it’s one of the oldest parts of Boston and is filled with both history and great foodie spots. One of our best Boston travel tips? Stop by Little Italy if you’re staying here to catch some of the best food in the area.
Boston is known for being very walkable, and Downtown is the place at the center of it all. In the financial hub of the city, expect older, cobbled streets, and stare up at glassy skyscrapers as you back onto the historical Freedom Trail. Use it as your base to explore Boston quickly and easily, especially with Old Town Trolley Boston stops nearby.
Few places in Boston do luxury quite like Beacon Hill. One of the oldest parts of Boston, it’s known for its steep streets and unbeatable views across the Boston skyline. Street lamps and cobbled streets make Beacon Hill truly beautiful; filled with historic landmarks, it’s a wonderful place to get a glimpse of Boston’s past.
Where Do Locals Eat in Boston?
Ever the example of eclectic eateries, Boston is home to Dakzen. A bustling Thai eatery with none of the pomp, you’ll find an array of authentic Thai classic dishes here, from Tom Yum soup to Chiang Mai’s local dish, Khao Soi. Located just off Somerville’s Davis Square, stop by for a quick bite in the evening to perk up your taste buds and energy.
Pizza is the world’s favorite dish for a reason, and you won’t find this Boston travel guide missing it. At Brewer’s Fork in Charlestown, there are homely, oven-fired pizza options that are perfect for fall-winter visitors, as well as a medley of other food staples. With beer and brunch sandwiches also on the menu, don’t be surprised if you’re back more than once.
If you’re looking for somewhere unique to eat, look no further than Cicada. Framed by tropical greenery, this Vietnamese café and wine bar has a distinctly artsy feel that will instantly make you feel at home. A place that comes to life in summer, you’ll find everything from spicy salads to fan-favorite Bánh Mì on the menu.
In every local’s travel guide, some eateries capture the heart as much as the tongue. In Boston, Tawakal Halal Cafe is your go-to. This Somali eatery is known for its homely and casual dining feel, drawing in food influences from its namesake country as well as East Africa and the Middle East.
If you’re searching for a lunchtime spot that ticks all your boxes, stop by Gene’s Chinese Flatbread Cafe for counter-service food that doesn’t compromise on taste. Serving up Xi’an-style Chinese food, their beef- and pork-stuffed flatbread sandwiches have become somewhat of a staple dish present in many a local’s travel guide.
Places to Drink
One of the most bustling drinks spots around, Time Out Market is nestled in the heart of Fenway, making it a prime spot for taking in the local ambiance afternoon or night. With everything from fine wines to local beers, it’s the perfect place to come with friends for a casual drink before moving on to your next drinks spot.
This aptly named bar does exactly what it says on the tin, and so much more. A staple on this local’s guide to visiting Boston, Drink is tucked away in the Seaport District and offers a strictly off-the-menu experience. Take your seat at a table or bar and enjoy as an expert bartender creates a cocktail for you from their premium spirits collection.
Nothing feels better than stumbling across a hidden gem like Offsuit. Coined as no frills, no fuss, enter this minuscule, 20-seat bar from a back entrance to find a collection of classic cocktails, each worth trying. With antique lamps, records on the wall and bookcases, it’s somewhere that feels a lot like Boston and home all at once.
Looking for a low-key kind of night? One of our best Boston travel tips here is to head to J.J. Foley’s. Located Downtown, it’s a reliable, homey hotspot for reasonably priced drinks – Perfect for those traveling on a shoestring budget and also for those wishing to live like a local on their weekends in Boston.
Kitsch and affordable, Delux Cafe is another great spot for those wishing to experience Boston like a local. With Elvis memorabilia, it’s certainly not a place you’ll forget on your travels — but all for the right reasons. Head here for a relaxed evening in the fall months for a cheap drink among friends. It’ll be your best introduction to the artsy South End.
For a small city, Boston has endless places to try — making it perfect for those wanting to get a taste of life as a local. Many people head to the Boston Public Market to immerse themselves in daily life or make the most of the Boston parks scattered around the city. One of our best Boston travel tips is not to be shy: Boston locals are a friendly bunch, and they will be more than happy to point you in the direction of their favorite haunts.
You’ll still want to tick off Boston’s tourist spots, as they hold much of the magic any local gem does. Many a Boston travel guide will recommend watching a game at Fenway Park and checking out museums, such as the Museum of Fine Arts. You will also want to take time ambling along the Freedom Trail, which is an excellent way to start or end a trip. For avid shoppers, Faneuil Hall is a prime location for getting your retail fix. No matter where you go, Old Town Trolley Boston is your best bet for getting from A to B.
Every city has its perks but none more so than Boston. Walkable, filled with history and defined by its eclectic hotpot of cultures, it’s ideal as a weekend break or a month-long immersive experience in equal measure. A local’s guide to visiting Boston will surely promise a city more than worth a visit, and they’d be right. Whether you’re a group of friends or a cityscape-loving couple, there is something here to suit everyone.
Like many cities, Boston comes alive in the summer months. Many a Boston travel guide will recommend visiting from June to October, where outdoor bars, baseball games, open-air concerts and summer activities make it a dreamy city to be in. What a local’s travel guide will say, though, is that fall is the best time to come if you want to escape busy crowds and expensive hotel rates. In October, you’ll see the trees light up in the city’s parks — a sight nowhere else can beat.