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How To Have A Fun-Filled Weekend In Boston, Massachusetts

boston travel guide
How To Have A Fun-Filled Weekend In Boston, Massachusetts

My usual style is solo travel; however, the stars aligned recently for myself and the good friends I met last year on my Latin America Way to San Jose trip with Intrepid Travel. Eric, the Kenyan guy living in London, decided to visit Boston, so Michelle, Tim and I went to meet him.

Typically when I visit a place I have a few focuses in mind: cool solo travel activities, hikes, cycling and offbeat adventures. For this trip, though, I simply wanted to relax and have fun with my friends. And fun we did have, of course mixed in with some prerequisite Boston history and culture.

Copy or tweak the below Boston travel guide for a fun-filled weekend of your own.

Getting There

Eric stayed with me for a few days before heading to Boston; but while his love of trains and extra leg room had him booking a ~$100 round trip train ticket, my love of saving money had me booking a MegaBus ticket for $40 round trip. MegaBus is one of my favorite options for drive-able trips, as their prices are incredible and the buses are comfortable (you can even purchase extra leg room seats for $7 or less). Note: while they say they have Wi-Fi I’m yet to see it be reliable.

boston travel guide
Wandering Washington Street in Boston

Getting Around

My friends and I pretty much walked everywhere — so easy to do in Boston. You can also rent bikes from the New Balance Hubway Bike-Share System, very accessible with 140+ Hubway stations in Boston, Cambridge, Brookline and Somerville. The cost is $6 per day, $12 for 72 hours, $20 for a month unlimited and $85 for the year unlimited, though note you’ll need to dock your bike every 30 minutes to avoid penalties. You can dock and then take it right back out.

boston travel guide
Walking the Freedom Trail in Boston. The brick line on the ground denotes the path for this important attraction.

For a few attractions like Harvard and Fenway Park we used the subway, which cost $2.65 for a one-way pay-as-you-go ticket. Here is more information on the local subway system. You can see below the subway map is pretty easy to read as long as you know your starting point, ending point and the direction you’re heading. Even though I’m good at reading subway maps I still use the CityMapper app, which works in many cities and tells you exactly how to get from Point A to Point B, where to exit a train, how to get around a city by bike and on foot (including how many calories you’ll burn), and provides offline maps.

boston travel guide
Boston subway map via the Massachusetts Bay Transportation Authority


We researched quite a few hotels, hostels, and AirBNBs, and HI Boston Hostel (HI Boston) was a clear winner. Our location was on the edge of Chinatown and the Theater District, walkable to all the major sites and nightlife areas. We paid $50 per person, per night for the 4- and 6-bedroom dorms we stayed in, including free Wi-Fi, access to free tours and activities like pub crawls and history walks, and a breakfast featuring toast, jams, cereals, juices, coffees/teas, yogurts, waffles and fruits. There were also numerous common areas for chilling out, playing pool and socializing. Bathrooms were shared but one-person-at-a-time for extra privacy, and each bed had its own light and outlets.


HI Boston has a communal kitchen, so we certainly made use of that (and the Trader Joe’s that was about a 20-minute walk away). We also explored some of Boston’s other budget-friendly bites, like:

Duck Tongue & Chicken Pho In Chinatown

In Chinatown at Joy Luck Hot Pot I savored a massive Tom Yum soup laced with lobster, beef, duck tongue, pumpkin, broccoli and vermicelli for ~$25. A bit pricier than what I’m used to in NYC where I do a buffet for $18, but still a blast. Note there is no alcohol served here and it’s not BYO.

Oh, and the duck tongue? If you’re picturing simply a tougher meat, as with beef tongue, the duck tongue tasted like hard cartilage poking my insides. If I went back I’d order the exact same thing sans tongue.

Nearby, Pho Pasteur provided a heaping bowl of chicken pho for $7.50.

boston travel guide
A heaping bowl of Pho from Pho Pasteur in Boston’s Chinatown

Eating Italian In The North End

In the North End you’ll find Boston’s “Little Italy,” where I wish I would have spent more time. There’s an awesome Italian deli called Salumeria Italiana selling quality Italian classics like cured meats, aged cheeses, handmade pastas, olive oils, vinegars and more. A spicy Calabrese-syle Soppressata is just what I needed to immerse myself in my own heritage without leaving the country (my grandma is from just outside Calabria).

boston travel guide
Italian signs in Boston’s East End

I also indulged in some pastry at Modern Pastry (instead of the famous Mike’s, as my cousin who lives in Boston wanted me to try something less trendy but still delicious). I had a Boston Cream Pie — invented at the local Omni Parker House — and the largest dessert lobster tail I’ve ever seen.

The main thoroughfare of the East End is Hanover Street — one of the oldest streets in Boston and originally a Native American path providing access to the waterfront. I’d recommend wandering and just seeing which aromas permeating from the many open air cafes and authentic eateries catch your attention.

boston travel guide
A Boston Cream Pie and a Lobster Tail (Sfogliatella) at Modern Pastry

Local Lobster In The Seaport District

My friends and I wanted some local seafood, and the locals we spoke to all touted Yankee Lobster Company in Boston’s Seaport District as one of the best for those on a budget. We got whole lobsters with slaw, fries and corn on the cob for $24.99, as well as a lobster roll full of meat ($14.99) and a filling salmon burger ($9.99). This is also where you can get Boston’s famous fried clams.

boston travel guide
Tim and Eric digging into their first lobsters — albeit in a confused fashion — at Yankee Lobster

The restaurant was about a three-minute walk to the fun Harpoon Brewery. Note: we went for the 4pm brewery tour on a Thursday and it was sold out until 6pm, so if you want the tour then book in advance. Alternatively, a Boston Brewery Tour of the city is fun idea.

At Harpoon we enjoyed just trying the many flights and Harpoon IPA-laced pretzels. Get the cinnamon sugar pretzel with maple and peanut butter dipping sauces to go with your beers (then promptly fall into a sugar coma).

Communal tables make it easy to socialize whether you’re with friends or traveling solo, though this would also be a great option if you’re looking for casual Boston date ideas.

Also make sure while in the Seaport District to take a walk along the waterfront. There are lovely photo opportunities here.

boston travel guide
Enjoying the flavors of Harpoon Brewery

History Meets Limitless Local Eatery Options

Faneuil Hall Marketplace (Quincy Market) — which has been a marketplace and meeting hall since 1743 — was my favorite foodie stop on the trip. I opted for the clam chowder and a baked haddock pie from Boston Chowdah, who won twice at the Boston HarborFest ChowdahFest. I like to taste different things in one sitting making this market — with everything from Clam Chowdah to sushi to fresh salads — a great choice. You’ll also find artisans selling non-food wares, entertaining buskers and, at night, the trees lining the market are lit up with whimsical fairy lights for a nice walk.

Tip: A Boston Sightseeing Tour or a Full Day City Tour of Boston and Cambridge are two options for exploring the market with a local guide while adding on additional experiences.

boston travel guide
Dining in Faneuil Hall Marketplace

A Unique Take On Roast Beef

One dish my cousin recommended that I just didn’t have time to try is braised roast beef tossed in barbecue sauce and served on a potato roll. “The Place” to get this is Kelley’s Roast Beef Co on Revere Beach. It’s on my list for next time.


Walk Through History

The Boston Freedom Trail is certainly something you should do to better understand US history and explore downtown Boston by foot. It’s 2.5 miles with 16 stops, including churches, historic homes and more. Some are free and others, such as the Site of the Boston Massacre and Paul Revere’s House, require admission. It’s easy to follow; there’s literally a brick line denoting the trail running through downtown.

boston travel guide
Old City Hall along the Freedom Trail in Boston

Take In The View

Along the trail you can visit the Bunker Hill Monument, a historic site commemorating the Battle of Bunker Hill that also offers an aerial view of Boston from 221-feet up. You’ll need to get a free ticket — and some fitness — to access the 294 winding steps that take you to the top.

boston travel guide
Climbing and chillen on the grass at the Bunker Hill Monument. Great spot to take in history, views and a picnic!

Parks Galore

As I’m a nature lover, I really loved wandering the 50-acre Boston Common. It’s part of the Freedom Trail and the country’s oldest city park, dating back to 1634. Within its bounds you’ll find softball fields, memorials and monuments, a bandstand, and a Frog Pond where visitors and families can wade in the waters.

From this park you wander straight into the Boston Public Garden, dating back to 1837. Here there are 24 acres of bridges, gardens, trees, hanging moss and a pond with swan boats you can ride for a small fee ($2-$3.50 for a 12-to-15-minute ride).

Connected to this large park is a greenway of beautifully manicured parks cut into pieces by cross streets. This strip brings together Boston Common and Boston Public Garden to form the Emerald Necklace, an apt name due to the shape and color.

boston travel guide
Enjoying parks and architecture in Boston

Girl Power

As you walk the above-mentioned parks take note of the historic Federal-style row-houses and streets featuring gaslights and brick sidewalks. It’s the type of stroll you don’t need an iPod for entertainment. There are also a number of public works, memorials and monuments as you walk, my favorite of which was the Women’s Memorial. The site showcases relaxed bronze female sculptures writing and thinking, and quotes from important women in history sharing Boston history. These include Abigail Adams (wife of the second US president), Phillis Wheatley (a former slave who became the first published African poet in the US), and Lucy Stone (an abolitionist and suffragist).

boston travel guide
The Women’s Memorial in Boston

Shops Galore In The Back Bay

The parks end about two blocks from a bustling hub of the Back Bay neighborhood called Newbury Street. There’s so much to see here! Along with big brand shops there are tons of little boutiques, a mix of luxury and thrift retail, book shops, cafes, comic venues and artisanal eats in beautiful renovated brownstones. It reminded me of Bleeker Street in the West Village in my home of NYC where there’s a lot to experience in just a few blocks. Some favorite stops:

boston travel guide
Newbury Street in Boston
  • I spent about an hour in Trident Booksellers and Cafe, an awesome bookstore with funny cards, unique gifts, mandala coloring books, inspiring quote-laced items, literary-themed temporary tattoos, coffee table books, graphic novels and more — including a cafe.
  • In every city I visit I try to eat at an homemade ice cream shop, and Emack & Bolios did not disappoint. The “hippie ice cream store” is now a chain, but was started in Boston in 1975 by a lawyer and self-declared hippie who worked pro bono mainly with the homeless, civil rights activists, Vietnam War protestors and big name bands like Aerosmith and U2. Cool backstory, but the real reason I went in was because their ice cream is all natural and void of fructose and dextrose. Plus, they offered 100-calorie-per-scoop probiotic live culture ice cream. The giant waffle cones dipped in fudge and cereal and the micro brewed sodas helped, too. I had the Black Raspberry Chip live culture ice cream, refreshing on a hot day.
boston travel guide
Yummy Emack & Bolio’s
  • I’m a hardcore hot head, so the sandwich board at Pavement Coffeehouse touting cayenne ginger ale beckoned me in. Yum! They also do an indulgent Spanish Latte laced with sweetened condensed milk and a monthly comedy night.
  • For me eating healthy isn’t about avoiding carbs, gluten or meat; it’s about eating natural. So Wich!t Sandwich was perfect as their thing is salads, soups and sandwiches made with all natural ingredients. Eats also come with homemade fries and condiments. Recommendation: the “Carolina Pork” featuring smoked pulled pork, barbecue sauce and tangy coleslaw on a brioche bun.
  • I’m obsessed with anyplace offering free tastings, especially if the free tastings are delicious. Boston Olive Oil Co. features over 60 varieties of olive oil and balsamic, all available to sample in small paper cups and with tiny breads. Along with varietal bottles they infuse products with ingredients like truffle, blood orange, chipotle, cilantro and garlic, and staff are happy to help you pair. I ended up buying Roasted Walnut Oil and Blackberry Ginger Balsamic, which paired insanely well together.

A Somber Experience At The New England Holocaust Memorial

One of the most moving sites I visited in Boston was the New England Holocaust Memorial, located along the Freedom Trail. It’s interactive in that you walk through its six towers representing six major extermination camps, each engraved with the unique ID numbers of those who lost their lives during the Holocaust. There are also messages to help visitors better understand the horrific events that took place. The towers emit smoke from the ground, a particularly emotional effect when you walk through at night.

Get Smart At Prestigious Schools

HI Boston offers free walking tours of Harvard University — one of the USA’s eight Ivy League institutions — though you can easily take the subway to the Harvard Square stop on the Red Line. Along with admiring the beautiful campus buildings there are lots of activities to do here and even a free audio tour of the campus.

Nearby is also the Massachusetts Institute of Technology (MIT), where you can visit the interactive MIT Museum and its many futuristic technology and science exhibitions. Right now they have an interesting exhibit with creation stations helping you understand photography as a tool for communicating science and technology theories.

This area features a number of unique tours, including a Haunted Harvard Square Ghost Tour, Harvard “Hahvahd” Campus Walking Tour and a Historical Hysterical Tour of Harvard with costumed guides and lesser-known history.

boston travel guide
Photo via Harvard Square

Enjoy Booze & Baseball Culture At Fenway Park

Of course, no trip to Boston would be complete without seeing a Red Sox game at the historic Fenway Park. I’ll admit, I was hesitant to do this as I don’t really enjoy watching sports (unless it’s a soccer match in Colombia where I can salsa dance in my seat); however, my friends really wanted to go. Since the tickets were only $30 each I sucked it up and went — and had a blast. Yes, the wine and stadium hot dogs helped, but in general it’s a fun atmosphere whether you’re a baseball fan or not. Plus, Fenway Park is an attraction in itself, the oldest ballpark in Major League Baseball and home to the Red Sox since 1912.

boston travel guide
Having fun at Fenway Park in Boston

Eat + Party On Historic Union Street

Cobbled Union Street provides a nice opportunity for indulging in history, literally. Have some “chowdah,” raw oysters, lobster ravioli and other seafood delights at Union Oyster House, a National Historic Landmark open since 1826 and one of the USA’s oldest restaurants.

I also had a blast seeing live music at the Green Dragon Tavern, established in 1654 and a favorite hangout of Paul Revere and John Hancock. It was also an important site for Pre-Revolutionary War organizing. Note though that the original tavern was in another location, and some doubt its affiliation at all. Either way, it’s a fun spot.

Live The High Life At The Colonnade Hotel’s Roof Top Pool

Called RTP (Roof Top Pool) this seasonal activity was our one splurge, though the Colonnade Hotel was kind enough to comp a cabana for my friends and me (thank you!).

The 12th story rooftop pool is typically $45 admission for non-hotel guests, and features a great aerial view of the city. There’s also a pool, fun dance music and refreshing cocktails (I loved the vodka-focused “Cucumber Cooler,” and the “Pina Colada” was a delicious dessert). If you think about the price of admission for most observation decks it’s not a bad deal.

While the cabana prices aren’t cheap — they’re listed below — it’s worth it if you’re with friends and want a taste of Boston’s laid back luxury. We had a blast getting tipsy, watching sports on the cabana flatscreen, and alternating between dips in the pool and laying out in the sun. In fact, I came back from Boston looking like I’d gone to the Caribbean.

Note: The pool is closed to the public on Saturdays and Sundays so renting a cabana is the only way non-hotel guests can get access on the weekends. Rental prices range from $250-$450 plus food and beverage minimum for up to four people.

boston travel guide
Rooftop cabana fun at The Colonnade Hotel Boston

What would you add to this Boston travel guide?

About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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Hi, I’m Jessie on a journey!

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  1. Eric on at 10:01 am

    mmmm! legroommmm…! Nice write up Ms. Nice to see you guys again.

  2. Camilla on at 9:46 pm

    Great!!! Visited Boston in 1 day (less than a day actually) and I loved their city so much!

  3. Jordan on at 11:04 pm

    Loved your list, I recently visited Boston and loved it. Next time I go I will have to check out some of the stuff on your list that I missed this trip. My visit actually led to be creating a blog and my first post is on this great city,

  4. vertoe on at 3:34 pm

    Really useful travel guide about and informative content about boston.Thanks for sharing.

  5. Daniel Barker on at 1:36 pm

    This is an awesome guide for anyone looking to explore Boston! I’m so excited to plan my trip and explore all the great things this city has to offer. Thanks for sharing!

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