Boston Weekend Guide: The Ultimate 48 Hour Itinerary
If you know me, you know I love weekend getaways. I need these breaks from my normal routine. And 48-hours is the perfect amount of time to explore and get the taste of a city.
After moving to New York, I knew Boston had to be one of my first weekend trips. The history, culture, and food really attracted me to this city. Let’s be real, one of the major reasons I love traveling is the chance to try different foods. And Boston is full of incredible restaurants, bakeries, and bars.
So if you are planning a trip to Bean Town, check out my Boston weekend guide. This is packed with my itinerary, tips, and suggestions for a perfect 48-hours in Boston.
Boston Weekend Guide
Getting Here
Ok, so I visited Boston as a weekend getaway from NYC. To make this affordable, I took a Greyhound bus. The trip was about 4.5 hours and cost roughly $60 (round trip). The bus dropped off at South Station, which was convenient to the North End and Waterfront neighborhoods.
Of course, you will need to decide what works best for you. You could drive to the city, just remember to factor in parking costs. Or, you could fly into the Boston Logan Airport. This international airport is one of the busiest in New England.
Where to Stay
If you’ve read my Budget Travel Tips, you won’t be surprised that I used Priceline Express to book my hotel. Air BnB and hotels can get pricey in Boston, so consider using Priceline Express to snag a deal. You can find some hotels on this site for less than $100 a night.
I stayed in the Club Quarters hotel in between Downtown and the Financial District. This area was a little quiet at night, but overall was a great location for everything I wanted to do in Boston.
The major tourist attractions are in North Boston, so consider staying near Beacon Hill, the Waterfront, or the Financial District.
Transportation
If you have a car during your weekend trip, you should have no problem getting around Boston.
For those of us who don’t have that option, Boston is still easy to navigate. This is a walkable city. Once you are in North Boston, you can easily walk to the major attractions and historical sites.
You can also use the bus or subway to get around Boston. The T services most of the city. A CharlieCard costs $2.25 for a oneway trip. You can also purchase a day pass for $12 that includes unlimited subway or bus trips.
Friday Night
Alright, let’s get to the fun stuff! As I mentioned earlier, my favorite way to experience a city it through food. So most of tonight is going to be food-focused. But trust me, you don’t want to miss the Italian food in this city. And that is exactly where we are starting.
Dinner in North End
You are now entering Boston’s Little Italy. Italian immigrants began settling here in the 19th century. They brought their traditions, customs, and culinary arts with them.
This neighborhood is filled with delicious Italian carbs. And there are more than a few places to get your fill of pasta and bread. But some of the best spots are:
You won’t be disappointed with any of those restaurants. But if you want the best experience, you need to check out Giacomo’s. This is the essential North End Italian restaurant. Get ready for some outstanding pasta dishes (I had the best lobster ravioli of my life here).
Just make sure you come prepared. This is a cash-only and no-reservations restaurant. The line will stretch around the block. And you will be rushed to leave your table as soon as you finish eating. But trust me, the meal is worth it! Especially when you try their famous Fra Diavolo sauce.
If you’re ready for something sweet, stop by one of the two rival North End cannoli shops. (Or try both, no judgment!) Spoiler alert, Mike’s Pastry was my fav.
Comedy Show
I’m not sure if you guys know this, but I love live comedy shows. Especially improv. So, for whatever reason, I usually avoid stand-up shows. But I decided to check out The Hideout while I was in Boston. And I had a great time! The line-up was funny and I stepped out of my improv-bubble.
So if you didn’t spend your entire night in line at Giacomo’s, head to Faneuil Hall for an evening comedy show. Hideout Comedy features local comedians every Friday night at 8 and 10 pm. Tickets are just $10.
Just be prepared. At night, Faneuil Hall is pretty empty compared to the tourist-filled walkways you will experience during the day. Most of Faneuil Hall shuts down in the evening so this area really clears out. But if you are looking for a post-show drink, consider checking out Beantown Pub.
Saturday
Breakfast
The best part about weekend trips? No guilt about eating desserts for breakfast! We are going to start this Saturday morning at one of Boston’s best cafes, Flour Bakery.
Here you will find a menu filled with pastries, cookies, and pies. (And if you don’t want a sweet, they also offer sandwiches)
My picks? Go for the brown butter cinnamon roll or sticky bun. You can’t go wrong with either.
You will find Flour all over Boston and Cambridge. But when I visited, I checked out the Farnsworth St-Fort Point location. This Flour is in a quiet neighborhood and offers plenty of outdoor seating.
Coffee
Yes, you could get coffee at Flour. But, if you want my recommendation for a delicious iced vanilla latte, head to Sorelle Bakery & Cafe. This is a nice, open coffee shop with friendly baristas. They also offer a full breakfast menu, so if for some reason you don’t want a cinnamon roll, you could order a bagel sandwich here. (But trust me, you want that Flour cinnamon roll)
If you decide to visit the Flour on Farnsworth St, Sorelle is only a 6-minute walk from this bakery. Even though it is short, this walk takes you over the Congress St Bridge for a nice view of the Harborwalk and Fort Point Channel. You will also pass the Boston’s Children Museum and Boston Tea Party Ships & Museum.
Walking Tour
Alright, it is time to see Boston’s sites. And walking tours are one of my favorite ways to explore a city. Boston conveniently connected their major historical sites with a walking path known as the Freedom Trail. This 2.5-mile trail takes you past 16 sites that shaped America’s history.
Along the trail, you can see Faneuil Hall, Paul Revere’s House, Boston Common, the Old North Church, and more. There are a few ways you could experience the trail.
- Follow the official Freedom Trail map: If you wanted to see every site, simply follow this map and the red-bricked pathway. Signs at each site give you a brief description of the significance and history.
- Follow a Self-Guided Tour: This guide also covers the entire Freedom Trail, but is more of a walking tour instead of just following a map.
- Sign up for an Official Tour: The Freedom Trail Foundation offers daily public tours. The tours are led by 18th-century costumed guides. Adult tickets cost $12.
- Take a Free Tour by Foot: This is my pick! I love Free Tours by Foot and I have taken their tours all over the world. They offer a 2-hour Freedom Trail tour that covers the main sites. Since this is a “free tour” you don’t have to pay for a ticket (but you still need to reserve a spot online). And please tip your guide! Yes, it’s free, but you are still expected to tip. Check their website for updates, but this tour currently starts at 10:30 am.
Lunch at the Market
After a walking tour, you’ve probably worked up an appetite for lunch. Time to check out one of Boston’s popular markets.
- Faneuil Hall Marketplace: Since the 18th century, this has been a gathering place for Bostonians. Sam Adams, George Washington, Susan B Anthony, and Bill Clinton have all used this hall as a speaking and rallying center. Unfortunately, the historical Faneuil Hall is currently under renovations. But you can still visit the Marketplace, which is filled with food stalls.
- Boston Public Market: If you want a less touristy lunch, check out the Boston Public Market. This is a year-round indoor market filled with New England food vendors. (Seriously, everything here comes from New England) The Public Market is only a 5-minute walk from Faneuil Hall, so you could even check out both!
Sam Adams Brewery Tour
When in Boston you need to have a Boston lager, right? So why not enjoy one in the Sam Adams Brewery?
So full disclosure, this isn’t a production facility. You won’t see bottling. But this is a test site where they create beers for competitions and local bars. And the tour includes a walkthrough of the Sam Adams brewing process and a tour of the facility. And it ends with free beer! Yes, at the end of the tour you are given free samples of Sam Adams. If you want to stay longer, you can enjoy another beer in the tap room.
Tours are offered 6-days a week (the brewery is closed on Sundays) on a first-come-first-serve basis. Check their website for available times.
The Brewery is located outside of Boston’s city center. If you are following this guide, you can take a 30-min metro trip from Faneuiluial Hall to the brewery. Take the Orange Line from State Street to Stony Brook. From here it is a 5-min walk to the brewery.
Get Educated
We are ending out Saturday with a late afternoon stroll through Harvard’s campus. If you want to follow a self-guided walking tour, this is a great option. If not, just soak up the history and beautiful architecture of America’s oldest university.
Harvard is a 40-min metro trip from the brewery. Take the Orange Line from Stony Brook to Downtown Crossing. From there, transfer to a Red Line. Take this to the Harvard station.
Once you are done exploring the campus, check out Harvard Square for dinner. This square is filled with restaurants and bars. If you want a classic Harvard experience, stop by Pinnochio Pizza. This unassuming shop has been serving Sicilian squares to Harvard students (including Mark Zuckerburg) for over 30 years.
Dessert in North End
If you didn’t try the cannolis last night, its time to visit the North End again (or even if you did, no judgment!) Mike’s and Modern Pastry are the top two Italian pastry shops in the city. And they both serve delicious cannolis. You really need to try them both to see where you stand on the rivalry.
Sunday
Breakfast at Tatte
I am so excited about Sunday’s itinerary. This is a relaxed and classically Boston day.
We are starting with breakfast at one of Boston’s most popular bakeries. Tatte Bakery and Cafe first opened in 2007 and they haven’t slowed down since. Especially on a Sunday, these bakeries will be packed. But embrace the crowds and know you are about to enjoy a delicious meal.
Their brunch menu includes classic pastries, coffee, and breakfast sandwiches. If you want a more unique dish, try the Shakshuka. This North African-inspired recipe includes tomato sauce, vegetables, cheese, and eggs.
Tatte shops are scattered around Boston and Cambridge. I suggest visiting the Beacon Hill location. This will give you the opportunity to explore this historic and picturesque neighborhood.
Acorn Street
While you are wandering along brick sidewalks past Federal-style rowhouses and gaslamps, make sure to look for Acorn Street. This is only 2-min from the Beacon Hill Tatte location. This cute, quiet street is one of the most photographed streets in the country.
Explore Back Bay
For the rest of the morning and early afternoon, explore Back Bay. This area is filled with some of Boston’s popular sites (like the Make Way for Ducklings statue and Newberry Street).
Consider following this walking tour. Along the way, you will explore the Public Garden and Copley Square. If you don’t want to do the full tour, spend some time relaxing in the Public Garden. This green space is a relaxing space to read or enjoy a warm Sunday morning.
Cheer on the Red Sox
When they are in town, go to a Red Sox game. The Red Sox are such an iconic Boston institution. I’m really not a baseball fan, but I still enjoyed my afternoon at Fenway. Get a Fenway frank, cheer on the Sox, and enjoy the energy of the stadium.
If you can’t make it to a game, consider touring the historic Fenway Park. This is still a great way to experience Boston’s iconic ballpark. The 60-min tours cost $20 for adults.
I hope you enjoyed this Boston weekend guide. Let me know if you are planning a weekend trip to Boston! I would love to hear about your itinerary.
Looking for more? Check out these Boston Guides:
What You HAVE to Eat in Boston
25 Free & Cheap Things to do in Boston
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