The Ultimate Guide to Exploring Boston

Complete Guide to Exploring Boston
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Boston is the capital of Massachusetts and lies on the east coast of the United States.  Where the Atlantic meets the eastern border, is where you’ll find this city packed full of charm and history.  Dating back to 1630, when it was founded by the British, Boston played a crucial roll in American history.  All thanks to the Boston Tea Party, which united the 13 American colonies to join together and fight for independence, which ultimately started the American Revolution.

Aside from being able to walk through American History, there is so much more to see and do in the city.  From public parks to opulent architecture and fantastic shopping.  Intimate restaurants and crowded breweries.  Don’t miss out on anything with this complete guide to Boston.


 How to Get Around Boston


Transportation from the Airport to the City

Boston Logan International Airport services the city of Boston.  It’s located in East Boston and has a train (known as the T) and bus system that runs from the airport to the city.  The two T lines that run from the airport to the city (and vice versa) are the red line and the blue line.

The Red Line will connect you to – Cambridge, Downtown Boston, Harvard, Mass General Hospital, and MIT.  The Silver Line Route SL1 will connect you, for free, to the red line.  Here you can purchase a CharlieTicket for $2.75 (paper ticket) one way ($2.25 if you manage to get a plastic, reusable card).

The Blue Line will take you to East Boston or to the Orange Line, which will connect you to – Back Bay, Boston College, Boston University, Brookline, Downtown Boston, Fenway, Longwood Medical Area, Newton, and Northeastern University.  To access the blue line from the airport, hop on the free Massport shuttle buses, route 22, 33, or 55.  This bus will take you to the Airport Station (blue line) where you can purchase a CharlieTicket for $2.75 one way.


Confused?  Don’t be!  Along with useful information, this guide to Boston will give you loads of resources!  Download the free “Transit” app for easy directions to wherever you’re going!


Train Transportation within Boston

Boston relies on the T to navigate through the city.  While the system has flaws, and can oftentimes be delayed due to construction, it tends to be the fastest and cheapest way to get around the city.  While a one-way CharlieTicket will run you $2.75, you can get a one day pass for $12 or a week-long pass for $21.25 if you plan to ride the T often.

Ultimate Guide to Boston

*This picture was taken from Google images, and links to the Boston Discovery Guide*

The main colored “lines” concerning train travel are the blue line, red line, orange line, silver line, and green line.  These all branch out into Boston and surrounding areas, while somehow crisscrossing each other forming a tangled web of transportation.

Car/Ride Share Transportation

I would not recommend renting a car while in Boston.  The streets are congested, the street parking is limited, and the parking garages are costly.  Plus with the T servicing the city you truly don’t need one.  However, if you plan on day-tripping out of Boston or decide that you do in fact want a car there are many places to rent from.  I’ve found the easiest way to go about renting a car is to rent right from the airport.  I use Discover Cars to compare prices across multiple different rental companies.

As far as ride share, you can use both Lyft and Uber to get around.



Where to Stay in Boston

When searching for a hotel/Airbnb in Boston, I would recommend staying in one of the following neighborhoods:


The Best Things to See and Do in Boston



Complete Guide to Boston - Fenway Stadium

Catch any number of sports games!  Boston has some of the best sports teams from football all the way down to hockey.  See the Red Sox hit a homer at the iconic Fenway Stadium.  Watch the Patriots defeat whoever is in town.  Or see hockey players exchange punches at a Bruins game!



Complete Guide to Boston - The Freedom Trail

Learn the history of America as you walk along the Freedom Trail.  The Freedom Trail is 2.5 miles long and runs from Beacon Hill to Charlestown.  While you can take a free tour, I followed directions from here and was able to make the walk on my own.  I will say, however, that once you hit Paul Revere’s House, the walk seems to become bland.  The most interesting history is at the beginning of the trail so if you don’t have time to see it all, stick with the first half.





Complete Guide to Boston - Shopping on Newbury St

Shop on Newbury Street.  Newbury is referred to as the “Rodeo Drive” of Boston.  Located in Back Bay, you’ll find a number of stores ranging from designer to boutiques, and cheaper stores such as Nordstrom Rack.  Or if you’re looking for more boutique stores, hit Charles Street in Beacon Hill.



Complete Guide to Boston - Acorn Street

Visit Boston’s most picturesque street – Acorn Street.  Acorn Street is located on Beacon Hill and is one of the most photographed streets in America.  While it has recently become illegal to have a full-on “photoshoot” on Acorn Street, you’re welcome to bring your iPhone and snap a few pictures as you please.  Keep in mind that people actually live on Acorn Street and to please respect their privacy.



Complete Guide to Boston - Sam Adams Brewery Tour

Be a part of the fun and interactive, free, Samuel Adams brewery tour!  Led by people incredibly passionate about Sam Adams and the art of beer making.  A fun way to spend the day rain or shine!



Visit Harvard University.  You can take the red line from Boston to Harvard, getting off smack in the middle of this elite university.  Take a free walking tour of the school, or explore at your own pace.  There are tons of bars and restaurants in Cambridge to keep you occupied for the day.




Complete Guide to Boston - Public Garden

Relax at the Public Garden.  Part of the Beacon Hill neighborhood, the Public Garden is the oldest public garden in America.  Bring your own picnic set up, or choose to eat at the rotating food trucks that come and go throughout the year.


The Best Neighborhoods in Boston

Boston is comprised of over 23 neighborhoods.  Each unique in their own way.  East Boston has views.  Fenway has the iconic baseball stadium surrounded by bustling bars.  South End is where you brunch.  And Beacon Hill is where you walk through history!  Whether you’re in Boston for a short while, or a long time, these are the neighborhoods worth spending time in.

Boston Neighborhoods


Back Bay – An affluent neighborhood where you’ll find some of the best restaurants in Boston, the Boston Public Library, and Newbury Street; the Rodeo Drive of shopping.

Must do in Back Bay:  Walk along Newbury Street


Beacon Hill – One of Boston’s most historic neighborhoods where you’ll find the picturesque Acorn Street, boutique shopping on Charles Street, or the expansive and relaxing public park, the Public Garden.

Must do in Beacon Hill – Hang out at the Public Garden


Fenway – Most famous for the oldest baseball stadium in America – Fenway Park, there’s more to do than watch baseball.  Fenway draws a younger crowd, packing bars and restaurants late into the night.  Go country at Loretta’s Last Call or go bowling at Lucky Strike Social.

Must do in Fenway – Catch a Red Sox game or go on a tour of Fenway Park


Downtown Boston – Walk among the Boston skyscrapers while also passing historical sites and buildings such as the grounds where the Boston Massacre occurred.  While I don’t recommend staying in the area long (I haven’t found any great bars or restaurants in the area), it deserves a stop by.

Must do Downtown – Stop by the Old State House and Boston Massacre site for a taste of American history


Seaport – The Seaport district is a redeveloped neighborhood on the waterfront.  It boasts great bars, restaurants, and rooftops overlooking downtown and the Boston skyscrapers.  One of my favorite areas to hang out in for a “fancier” night on the town.

Must do in Seaport – Enjoy drinks on the rooftop of the Envoy Hotel


The North End – Boston’s “Little Italy” and for good reason!  Here’s where you’ll walk tiny, twisting roads, that seem to always end at a hole in the wall Italian restaurant.  Bursting with character, the North End is a must-see while in Boston.

Book a food tour in the North End with a local!

Must do in the North End – Eat Italian food while in “Little Italy”!


The Best Restaurants in Boston

Complete Guide to Boston - Where to Eat

Boston has no shortage of great restaurants.  While some I enjoyed going to for the mouthwatering food, others I enjoyed going to for the sheer ambiance.  From the hot pot to lobster rolls, and everything in between!  You can truly find anything you would dream of in Boston.


Beehive – Located in the South End, Beehive is a lively restaurant with music every night.  Not only is the food great but the atmosphere is top-notch.  If you can’t make it in for a full dinner, hang out at the bar and listen to whoever is playing for the night.  Or if you’re in town for brunch, stop by for their live jazz weekend brunch.

Hours of operation:  Monday-Wednesday 1700-2400; Thursday 1700-0100; Friday 1700-0200; Saturday 0930-0200; Sunday 0930-2400


Lolita – Located in Back Bay, this gothic decorated restaurant serves elevated Mexican food.  Best for their innovative margaritas and the cotton candy served at the end of the meal.

Hours of operation:  Sunday-Saturday 1600-2400


Neptune Oyster – Also located in the North End, Neptune Oyster is where you can get some of the best, and most fresh seafood in Boston.  In my opinion, Neptune Oyster serves the best lobster roll in all of Boston.  While you’re unable to make reservations, the wait is worth it.

Hours of operation:  Sunday-Thursday 1130-2130; Friday-Saturday 1130-2230


Pomodoro – Located in the North End, Boston’s “Little Italy”, Pomodoro is a small, quaint hole in the wall.  With no sign above the door, Pomodoro is the perfect intimate setting serving fantastic Italian food.  Being such a small restaurant, the service was extra incredible.  Our wine glasses were always filled (even when our bottle was gone!) and dessert on the house was served to everyone!  Pomodoro is cash only but there is an ATM across the street.

Hours of operation:  Sunday-Saturday 1730-2300


Reelhouse.  Located in East Boston, Reelhouse serves fresh seafood in a fancy feeling atmosphere.  Situated on the harbor with views of the Boston skyline, Reelhouse is the perfect location for a drink or food outside on a nice day.  During the summer water taxis service those from the other side of the bay over to East Boston.

Hours of operation:  Sunday-Wednesday 1100-2300; Thursday 1100-2400; Friday-Saturday 1100-0100


The Friendly Toast – With multiple locations throughout Boston, The Friendly Toast is your go-to place for brunch!  Serving mimosa flights, bloody mary flights, and breakfast, lunch, and dinner all day every day, The Friendly Toast can conquer any craving.

Hours of operation vary between restaurant locations


Toro – A Spanish restaurant located in the South End, Toro is a hot spot on the Boston restaurant scene.  Perfect as a solo traveler or for date night, Toro serves their food tapas style.  While you can reserve a table for lunch, dinner is determined on a first-come, first-serve basis.

Hours of operation:  Monday-Thursday 1200-1500, 1700-2200; Friday 1200-1500, 1700-2300; Saturday 1600-2300; Sunday 1030-1430, 1700-2200




The Best Bars in Boston

Boston has both casual and elevated drink spots.  There are bars that serve fancy cocktails, your classic beer, and even the Boston staple, the espresso martini.  While some of these places double as restaurants, I find it more enjoyable to sip cocktails and save the food for the restaurants mentioned above.


Banyan Bar + Refuge – This Asian fusion restaurant is located in the South End.  While the food was fine, it was the ambiance that knocked me off my feet.  I especially enjoyed their quirky décor and fresh, fun, and lively atmosphere.

Hours of operation:  Monday-Thursday 1600-2300; Friday 1600-0100; Saturday 1100-0100; Sunday 1100-2300


Bostonia Public House – Located inside The Bostonian Boston, head here for the classic espresso martini.

Hours of operation:  Sunday 1000-2400; Monday-Tuesday 1130-2400; Wednesday-Friday 1130-0200; Saturday 1000-0200


Citrus and Salt – Located in Back Bay, Citrus and Salt is a Mexican tapas restaurant.  With a quirky, edgy atmosphere, it’s a fun restaurant to sip on cocktails at the bar as you watch the bartenders whip up endless margaritas.

Hours of operation:  Monday-Wednesday 1600-2400; Thursday 1130-1400, 1600-2400; Friday 1130-1400, 1600-0100; Saturday 1100-1500; 1600-0100; Sunday 1100-1500, 1600-2400


Drink – Located in Seaport, Drink is a menu-less cocktail bar.  Belly up to the bar and describe to the bartender what you typically like and they make it up for you!  While Drink doesn’t have a cocktail menu, they do have a wine and food menu.

Hours of operation:  Sunday-Saturday 1600-0100


Night Shift Brewing – Local craft beers in a lively atmosphere.  Located in Everett, hang out at Night Shift more so for the atmosphere than the beer.

Hours of operation:  Monday-Saturday 1100-2300; Sunday 1100-2000




The Best Day Trips from Boston

You can skim the surface of Boston in about three days.  If you plan on staying longer and are looking to venture outside of the city, there are tons of places to take day trips too!  My favorite thing about the east coast is how easy it is to cross state borders in a matter of hours.  Want to eat lobster on the coast of Maine?  Head north!  Looking for hiking?  Drive to Acadia National Park!

While I was in Boston I was able to make two days trips out of the city.  My first-day trip took me to the fun and fresh gay capital of America, Provincetown, MA.  Where the art scene is as good as the seafood and a festival can be attended any summer weekend.  My second-day trip took me to Newport, RI where I felt part of the rich and famous touring the infamous Newport Mansions.  If you fancy a day trip I’d highly recommend checking out these two locations.  And if you need to rent a car to get there, you can book here.


Did I miss anything in this guide to Boston?  Let me know in the comments below!


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Disclosure:  This post may contain affiliate links, meaning I get a commission if you decide to purchase through my link, at no cost to you.


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Kylee is a Neonatal Intensive Care (NICU) nurse passionate about making travel affordable and accessible to nurses. Inspiring nurses to travel both near and far, Kylee began Passports and Preemies in 2017 while volunteering in Skopje, North Macedonia as a way to reach nurses and advocate for the prevention of nurse burnout by traveling. Kylee is the original creator of the “8 Day Vacay” – a vacation geared towards nurses who aim to take advantage of the potentially 8 days off between work weeks with no need to use PTO.

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  1. Wandering Crystal
    June 15, 2019 / 3:40 pm

    Amazing! I can’t wait to get to Acorn Street – how pretty are those cobblestones?! I sure wouldn’t want to be walking around there in high heels though. I will follow your advice and walk the Freedom Trail! I know there are two cemeteries along the Freedom Trail I want to visit.

    • June 16, 2019 / 8:16 pm

      There are loads of cemeteries along the freedom trail! I thought of you when I passed them! Are you going to Boston for TravelCon?

  2. June 20, 2019 / 4:57 pm

    Wow! I’ve always wanted to visit Boston but your guide has me looking up flights. I love the charming neighborhoods and added the Freedom Trail to my bucket list. Thanks for the tips!

    • June 22, 2019 / 6:29 pm

      Ooh I love to hear this! The neighborhoods definitely sold me. All so different and charming in their own ways!

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