New in Town: The Ultimate First Time to Boston Guide

July 23, 2019 | , , , , ,
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Navigating Boston On Your First Visit

chowder and quincy market

Photo Credit: Bites of Boston

Welcome to Boston! Whether you’re here already or you’re planning a trip, you’ve landed on the right page. We are here to help you navigate the bustling city of Boston so that you can spend the most time having fun! Whether it’s a girls’ trip, guys’ trip, family trip, or couples’ trip, Boston is the place to go and we’re here to help you make your trip the best it can be. From public transportation to where to stay, what to eat, and what to do, we’ve got you covered.

Boston is really the city that has it all — it’s rich in history and culture, has amazing food, is a huge sports town, has beautiful and diverse neighborhoods, and is easy to navigate. It’s hard to want to leave, we know! We want you to soak up every moment you have here without wondering if you’re missing out on something awesome, so check out the info below and soon you’ll go from Boston first-timer to Beantown pro.


airport sign

Photo Credit: Knights Limo

Boston’s airport is called Boston Logan International Airport and it’s located just three miles outside of the city making it very easy to commute to and from. It’s a quick drive — Taxis, Uber, and Lyft are very easy to grab — or a simple trip using public transportation, which is easy and affordable!

You can take the Silver Line SL1 bus directly from the airport to South Station in downtown Boston for FREE, with an additional free transfer to the Red Line trains if you want it. The Silver Line SL1 is accessible for the disabled and runs from approximately 5:30am to 12:30am every day of the week. You can also take the Blue Line train from the Airport Station to head into the city and connect to other trains. The Blue Line runs from approximately 6:00am to 12:30am every day of the week. For even more information click here.

Public Transportation

There is both a full train and bus system in Boston called the T. In order to ride the T you can purchase a paper ticket that you can re-fill with money or you can get a Charlie Card from one of the T attendants. You fill your Charlie Card, a hard plastic card, with money at one of the stations or on the train itself (cash only if it’s on the train). Each fare is less when you pay with a Charlie Card so if you can get one do it. You can explore all over the city using the T and we suggest it! Here’s a map of the T for you to start planning.

map of the mbta trains

Photo Credit: MBTA

Where To Stay

inside the liberty hotel

Photo Credit: The Liberty Hotel

As any big city would be, Boston is FULL of hotels of all different kinds. From big names that you’ll recognize to really cool independent hotels. Some of the hotels we love that are unique to Boston are listed below for you to check out. You can’t go wrong with any of them!

The Lenox Hotel

This landmark is beautifully classic and in the heart of Boston’s most popular neighborhood, Copley Square, and will give you the true Boston experience.

Omni Parker House

This elegant hotel opened in 1855 and is a historic symbol in Boston, not to mention the home of the famous Parker House Rolls and Boston Cream Pie.

The Liberty Hotel

This hip, luxury hotel is actually a converted prison. Now it houses some of the city’s most trendy restaurants and hotel interior, nodding to it’s past, making it a mysteriously fun place to stay.

XV Beacon

This charming little hotel is located right near the State House and Beacon Hill where cobblestone sidewalks criss-cross with each other. The hotel has modern, dark interior that is mixed with the old-world elegance of Beacon Hill.

Fairmont Copley Plaza

Also located in the heart of Copley Square, close to any- and everything you may need, this hotel has stunning interior and will make you feel like you royalty.

Boston Park Plaza

This modern hotel located right near Boston Common is the perfect place to stay during your first trip to Boston. It’s located walking distance to some great landmarks, neighborhoods, and restaurants.

Hotel Commonwealth

This hotel famously packs up from April to October when the Red Sox are in town. It’s located in Kenmore Square, just at the east edge of Boston University’s campus and has some great restaurants attached to it. If you can get in between the baseball and college crowds it’s a beautiful and fun place to stay.

Boston Harbor Hotel

Located right on Boston’s harbor in downtown, this hotel gives you the best of both worlds, combining city and maritime charm. It’s also close to some great sites, shopping, and restaurants.

The Whitney Hotel

This boutique hotel is brand new and located at the end of Beacon Hill. They offer some of the city’s best hospitality with sophisticated simplicity.

The Eliot Hotel

This award-winning hotel is located in the heart of beautiful Back Bay, boasting it’s own beauty and elegance. It’s close to everything and worth the trip alone to stay there.

The Envoy

This super modern hotel in Boston’s Seaport is one of the coolest spots in town to stay. From it’s hip interior to it’s stunning roof deck and amazing food, it’ll be hard to even leave the hotel but luckily it’s close to so much awesome stuff that you’ll have to.

Things To Do

paul revere statue and old state house

Photo Credit: @alexsip1215 via Instagram

There is sooooo much to do in Boston and there’s something for everyone! This list is just the beginning of what you can do when you visit Boston for the first time, but it’s safe to say that if you start here you won’t be disappointed!

Visit the Museum of Fine Arts (MFA)

The MFA is the fifth largest museum in the United States, containing more than 450,000 works of art. You could spend an entire day alone here getting lost in all the works!

Visit the Isabella Stewart Gardner Museum

For a museum smaller in size but not in richness, visit the Isabella Stewart Gardner Museum. It has the feel of a Venetian Palazzo with a lush courtyard in the center. It’s art collection is from all over the world including paintings, sculpture, tapestries, and decorative arts.

Take a Food Tour with Bites of Boston Food Tours

For a truly unique Boston experience join Bites of Boston for one of their walking neighborhood food tours where you’ll learn fascinating history about the area as well as tasting some of the neighborhood’s most delicious bites. They run tours in four different neighborhoods including a Classic Bites Tour where you’ll learn taste some of the foods Boston is most known for and the history behind them. They have friendly and knowledgeable tour guides who are waiting to show you some of the awesome neighborhoods and food that Boston has to offer. Leave it all to them!

Visit Fenway for a Red Sox Game

One of the most famous baseball stadiums lives right in the heart of Boston. Go cheer on the World Series Champion Red Sox for a game or take a tour of the stadium. You can even stand right on the Green Monster itself to watch the action!

Walk Through Boston Common & Take a Swan Boat Ride

Boston’s beautiful public park, actually the oldest city park in the United States, is a wonderful place to stroll through, have a picnic, or take a swan boat ride. The greenery is lush and bright in spring and summer and picturesque in fall. There’s nothing like a New England fall so make sure to bring your camera!

Visit the Skywalk Observatory

See Boston from way up high! Take in the stunning views from the Skywalk Observatory, a truly unique experience.

Shop on Newbury Street

If you want to shop til you drop, Newbury Street is the place to go. With stores both local and big name you’ll need help carrying all your bags by the time you’re through. And as an extra bonus there are amazing restaurants and cafes all along the street to stop and refuel at.

Walk the Freedom Trail

For a true taste of Boston’s history check out the Freedom Trail. The Freedom Trail is a 2.5 mile red brick trail that will lead you through the streets of downtown Boston stopping at 16 noteworthy sites. You can walk all the way through or just pick some of the sites to stop at. If you’re a history buff, this is the activity for you!

Stroll Through & Eat in the North End

The famous North End is known as Boston’s “Little Italy.” The quaint streets are packed with little Italian restaurants and cafes letting out tempting smells of pasta and pastries. Walk through and experience it for yourself and let your nose lead the way.

Visit the New England Aquarium

One of the best attractions for all ages, the New England Aquarium is a global leader in ocean exploration and a great place to visit on your trip to Boston.

Walk Through Faneuil Hall Marketplace

Fanueil Hall Marketplace is always at the top of things to do in Boston lists because it has the history, the food, and the fun. Lined with cobblestones, this open air space was proclaimed “The Cradle of Liberty” by our nation’s fathers in 1742 and today is filled with restaurants and shops. There’s always a bunch of people both local and visiting. You can also hop on or off a Trolly or Duck Tour here.

Play Retro Arcade Games at A4cade

For an awesome night of retro gaming, think Skee-Ball and Frogger, head to A4cade in Cambridge. You’ll feel like you stepped back in time a little but will be reminded with the up to date craft food and drinks from Roxy’s Grilled Cheese that you are in fact in 2019.

What/Where To Eat

boston cream pie

Photo Credit: @bostonfoodgram via Instagram

Breakfast / Brunch


Photo Credit: Tatte Bakery

The Friendly Toast

Hip & retro diner serving comfort classics.

The South End Buttery

Neighborhood bakery and cafe.

The Paramount

Cafeteria-style spot serving American comfort food.


Bakery and cafe serving Mediterranean fare and photo-worthy pastries.

Little Dipper

Space-themed diner with all the diner classics.

Rosebud American Kitchen & Bar

Iconic diner setting serving chef-driven food and craft cocktails.

The Classics

lobster roll

Photo Credit: @down4dessert via Instagram

Lobster Roll

Check out the lobster roll from James Hook & Co.

Clam Chowder from Legal Seafoods

Classic and delicious in a lovely setting.

Baked Beans & Brown Bread from Beantown Pub

As classic Boston as it gets all around.

Boston Cream Pie Different Ways

Boston’s quintessential dessert. Explore different ways to eat it in Boston.

For the History Buffs

baked beans and brown bread

Photo Credit: Bites of Boston

Molasses Flood Foods

Check out these foods incorporating molasses in different ways.

Classic Sites & Bites

Visit these classic sites in Boston and eat great food along the way.

Tea Party

Take a look at all these unique ways to drink / eat tea in Boston.

Locally Owned / Unique Concepts

lots of food

Photo Credit: Shojo

Bootleg Special

Cajun-style seafood boils in an industrial-chic setting.


Trendy, mural-filled gastropub with modern takes on Asian fare.


Sophisticated and stylish supper club with incredibly creative food and drinks.

Citrus & Salt

Baja Coast-inspired Mexican food and drinks in a dining room with beach-y vibes.

Double Chin

Hong Kong cafe putting a modern and playful spin on Asian classics.

Saltie Girl

Intimate seafood-focused spot.

Alden & Harlow

Creative New American fare and cocktails in rustic Harvard Square setting.


A Latin Kitchen inspired by “taguaritas,” rustic, inviting, family-run eateries found along Venezuelan roadsides.

The Elephant Walk

Innovative French-Cambodian fusion with an earthy ambiance.


Classic Italian in a cozy setting serving fresh, homemade pasta.


Eastern Mediterranean dishes in a warm, welcoming interior with a peaceful garden patio.

New England Seafood

oysters and other seafood

Photo Credit: Island Creek Oyster Bar

The Daily Catch

Sicilian-style pasta and seafood in an intimate and rustic setting.

Yankee Lobster Co.

Low-key counter service spot with seaport views and delicious food.

Island Creek Oyster Bar

Farm-fresh raw bar, inventive and classic seafood dishes in a sophisticated setting.

Neptune Oyster

Tiny high-end oyster bar worth the wait.

James Hook & Co.

Waterfront shanty offering live lobsters plus prepared shellfish fare for takeout.

The Barking Crab

Lively waterfront seafood joint with open-air picnic-table dining and views of the Boston Harbor.


*For more check out our blog post on summer seafood here!

Good for Groups


Photo Credit: Cinquecento

Sweet Cheeks Q

Texas BBQ in a wood-filled setting serving big portions and to-die-for biscuits.


House-made pastas & other small plates are served at this casual-chic wine bar with a rear patio.


Rustic beams & brick walls adorn this upscale Italian restaurant that also offers outdoor dining.

Eastern Standard

Happening scene starring masterful cocktails and modern brasserie fare in a glamorous atmosphere.

On the Sweet Side

rice kridpie

Photo Credit: Flour Bakery

Union Square Donuts

Creative, fluffy, flavorful, addictive donuts.

Toscanini’s Ice Cream

Perfectly creamy ice cream in classic and inventive flavors.

Flour Bakery

Incredible pastries and more, known for their famous sticky bun.

Clear Flour Bakery

Tiny neighborhood bakery that always has a line but is absolutely worth the wait.

Mike’s Pastry

The go-to place for cannoli’s of all flavors and sizes.

Specialty Markets / Food Halls

cheese counter

Photo Credit: Formaggio Kitchen

Boston Public Market

Year-round indoor market with scores of vendors selling local produce, fish, gourmet treats, and more.

Formaggio Kitchen

Compact cheesemonger offering European and American varieties, plus beer, wine, and artisanal foodstuffs.

Time Out Market

BRAND NEW: Boston’s innovative eating-and-drinking destination features the city’s top chefs, most-talked-about restaurants and buzziest bars—plus the latest in arts and culture—all together under one roof.

Quincy Market

Shopping center with many stores & restaurants comprising three historic market buildings and a promenade.


Italian dining emporium with groceries, seafood markets and a dozen eateries.

Neighborhoods to Visit

Check out our neighborhood guides for the awesome neighborhoods below and get to exploring!



North End

Harvard Square


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