A Fun Weekend in Boston with a GoCity Pass

Spending a weekend in Boston is the perfect introduction to this busy, historical American city.

I love taking short, budget weekend trips to explore new cities. You get to experience a new atmosphere without using much PTO, if any, and you don’t have to spend much to make them happen.

To keep costs down, I tried out the GoCity Boston Pass. Let’s be honest: I do my research before I use a sightseeing pass, so I knew I was going to save money with this pass.

The question was whether or not it offered enough quality attractions that I’d be satisfied with my first weekend in Boston and not feel like I had missed out on anything.

So I built my Boston weekend itinerary entirely from sights included in the GoCity Pass, and it was totally worth it!

Not only did I get to experience the historical side of Boston that I’d always wanted to see, but I also got to do several fun things I wouldn’t have thought to add to my itinerary on my own. And I saved over $150 in the process.

I can confidently recommend this itinerary for your first weekend in Boston, whether you use the GoCity Pass or not. Let’s check it out!

GoCity gifted me a 2 Day All-Inclusive pass to Boston, but they did not sponsor the trip. I created my own itinerary and have come to my own conclusions about their product, which I recommend. This post contains affiliate links, so if you click a link and make a purchase, I may earn a small commission at no extra cost to you.

First-Timer’s Boston Weekend Itinerary

This was my first trip to Boston, and I wanted to see as much as possible. This city is a history and lobster lover’s dream, and I’m both of those things.

Even if you don’t care for the history, though, there are plenty of other fun things to do in Boston. There are specialty tours for Fenway Park, food, pubs, movies filmed here, and true crime, to name a few.

Go tour a famous college campus, or day trip to Salem. Visit the Lexington and Concord Battlefield, or find Louisa May Alcott’s Orchard House. Take the kids to the Boston Children’s Museum, Franklin Park Zoo, or the Lego Discovery Center.

Budget Tip: You can do all of those things for one price with a Boston GoCity Pass.

If you’re only doing one or two things, then skip the pass. But if you’re doing 3-4 per day, the pass will save you money.

Price it out before you make up your mind.

Here’s how I spent 2 days in Boston with a GoCity All-Inclusive Pass:

  • Day 1 – Historical Boston
    • Hop on, Hop Off Trolley Tour
    • Paul Revere’s House
    • Photos of Old North Church (entry not included in pass)
    • Freedom Trail to Copp’s Hill Burying Ground
    • USS Constitution & Museum
    • Bunker Hill Monument (free anyway)
    • Walking History Tour, including Boston Common, Granary Burying Ground, King’s Chapel, Omni Parker House Hotel, Old South Meeting House, Old State House, and Faneuil Hall
    • Eat at Parker House Hotel (original Boston Crème Pies and Parker House rolls)
  • Day 2 – Popular Boston Sites
    • MIT campus tour
    • Harvard campus tour
    • Peabody Museum of Anthropology
    • Harvard Natural History Museum
    • Harbor Sunset Cruise
    • Prudential Center Observation Deck: The View

It’s always best to group your activities by neighborhood or in a logical order so you don’t lose a lot of time crisscrossing the city.

If you use the GoCity Pass, their app has a very handy map that’ll show you everything in the area included in the pass and can be filtered by items you’ve favorited.

It makes planning out your itinerary super easy and fast.

You can do the same thing with Google Maps if you’re doing this without a sightseeing pass, but you have to take the time to save them to your personal list.

How to Get Around Boston

You don’t need a car for this Boston itinerary.

Even if you want to see some of the further out spots like Salem or Lexington and Concord, they can be reached by the T, Boston’s subway train system, and a short walk from the station.

Boston’s public transportation is good, but you can also use a hop on, hop off trolley tour to get around downtown to the specific tourist spots you want to visit.

We used both the T and a trolley tour the first day and just the T on the second day. We also made sure to choose lodging near a T station so it wouldn’t be difficult to get going each day.

Day 1 – Historical Sites

History is a big deal in Boston. The Mayflower landed here. The American Revolution started here. Famous authors, politicians, and statesmen lived here. Several Presidents have called it home.

Spend your first day in Boston taking in all the historical sites. You’ll move around often enough that you won’t get bored, and you’ll see some very American sites along the way.

Start with a Hop On, Hop Off Trolley Tour

Board at the beginning of the CityView Trolley Tour route, near the T station for the New England Aquarium.

It circles around the North End, briefly dips into Charlestown, comes back into downtown and loops around Boston Common before passing by Chinatown and returning to the Aquarium.

The drivers keep up a steady conversation filled with fun facts and jokes about the city. The jokes may be cheesy, but it’s good to laugh when you’re stuck in traffic.

Good to Know: Traffic can get backed up in Boston, so we found it to be a better use of our time to jump off immediately to see the sights rather than do a full circuit first and try for a second loop to start sightseeing.

Paul Revere’s House

The first stop on the trolley route is Paul Revere’s House in the North End. You have to walk a couple of blocks over, but it was easy to figure out.

It shouldn’t come as a surprise when you think about it, but Paul Revere’s house is small, just 4 rooms.

There’s a little gift shop and exhibit area in a separate building in the back, and the courtyard has one of the bells cast by Paul Revere.

His silversmithing is touched on briefly in the exhibits, but he’s most famous for his midnight ride to warn the American colonists that the British soldiers were coming.

You won’t need much time here. You can be in and out in 30 minutes if there’s no line.

Photos of Old North Church

Next, we followed the Freedom Trail to the Old North Church, zigzagging past a ton of Italian restaurants as we went.

There’s an impressive statue of Paul Revere on a horse in the Paul Revere Mall, a green space that backs up to the Old North Church property.

Entry to the church is not included in the GoCity Pass but you can get photos outside for free or buy a ticket to go inside. Tickets are $10 or less, depending on if you get an audio guide or not.

Copps’ Hill Burying Ground

Up the hill from the church is Copp’s Hill Burying Ground. You can follow the Freedom Trail brick path to get here, but it’s just the road directly in front of the church entrance.

This is a fun photo op, but we didn’t linger here too long. Snap a pic of the Freedom Trail marker, walk around Copp’s Hill for some more photos, and marvel at the Spite House (Skinny House).

Then continue down the road to catch the trolley again at the stop at the Steriti Ice Rink. You have another short ride, this time across the river to see the USS Constitution.

USS Constitution

Climb aboard a wooden warship and admire the oldest commissioned warship afloat in the world. “Old Ironsides” was one of the original six ships commissioned for the US Navy.

While it’s not exactly original materials anymore, having been repaired numerous times over the two centuries since it was first built, it’s not considered a replica either because it was never rebuilt from scratch.

Regardless, it’s a cool experience to step aboard and see how sailors in the late 1700s would have lived and served on the ship.

The National Park Service (NPS) has a very informative exhibit hall at their Visitor Center at the navy yard, but the ship has soldiers watching over it, not park rangers.

Across from the NPS Visitor Center is the USS Constitution Museum, ran by a separate entity that works in partnership with the NPS and other preservation and history groups.

If you’re short on time, you don’t need to visit both the visitor center and the museum. Pick one and tour the ship, and then head over to Bunker Hill.

Bunker Hill Monument

The Bunker Hill Monument and Lodge are a short walk from the USS Constitution dock, so we headed over for a quick stop. It’s an uphill walk on the way over from the navy yard, but all downhill on the way back!

Bunker Hill is an NPS-owned site and has free entry, so don’t worry that it’s not included in your GoCity Pass.

The monument was closed during our trip so we couldn’t climb it, but I bet it’s got great views from the top.

As it was, we snapped a few photos, saw the Prescott statue, and then went back to the navy yard to catch the trolley to Boston Common for a walking tour.

Good to Know: Traffic can be bad and slow you down. We had 45 minutes to get from the navy yard trolley stop to the Boston Common stop to catch the next walking tour, and we were still 10 minutes late.

It was a Friday, terrible traffic in midafternoon, and raining, which just made it worse. We probably would have been on time if we had disembarked the trolley at the Old State House and walked over to Boston Common. That’s how bad traffic was.

Freedom Trail Foundation Walking History Tour

I can’t recommend this guided walking tour enough! It was thorough, funny, and you see A LOT.

We spent most of our time in Boston Common and at the Granary Burying Ground, but our guide was also trying to keep us out of the rain. (Yes, these tours run rain or shine.)

You’ll start at Boston Common and see the Granary Burying Ground (a lot of famous people buried here), King’s Chapel, Omni Parker House Hotel, Old South Meeting House, Old State House and the Boston Massacre Site, and end at Faneuil Hall Marketplace.

I recommend purposefully skipping touring the Old State House first even though the trolley will pass it first. You can tour it after your walking tour ends without a lot of backtracking to get there.

Good to Know: If you arrive early to Boston Common, take a stroll around the common and the adjacent Boston Public Garden.

Photo Op: The bar from Cheers, the TV show, is on Beacon Street across from the Boston Public Garden. Get a photo, buy merch in the gift shop, and even get a drink if you have enough time.

Eat at Parker House Hotel

When you’re done sightseeing, or ready for some food, step inside the Omni Parker House Hotel and eat at their restaurant.

Home of the original Boston Crème Pies and Parker House rolls. Try them both!

You don’t have to be a guest at the hotel to eat at the restaurant. Reservations aren’t required but may be wise to have in peak summer season.

Day 2 – Popular Boston Sites

Tailor today to whatever interests you most. My husband and I are both engineers, so we wanted to geek out over a couple of college campuses and museums.

Maybe you’re a Red Sox fan and you’d like to tour Fenway Park. Or you’re a foodie that wants to eat your way through the North End.

Choose whatever speaks to you.

Here’s what I did:

MIT Campus Tour

The Massachusetts Institute of Technology is the top engineering school in the United States, and they have some cool stuff! Get a peek behind the curtain at a top-tier university.

You don’t have to be an engineer to appreciate this tour, either.

Did you know MIT has humanities degrees? You could get a degree in music theory from MIT, but you’d still have to take calculus, physics, and chemistry.

I was blown away that they have their own clean rooms so they can make their own microchips. Gone are the days of waiting months for IBM to make and ship them. MIT students don’t have time for that. They make their own.

Campus is also beautiful, on the banks of the Charles River and with some beautiful architecture to boot.

After our tour, we ate lunch at a Chipotle on campus right next to the T station before continuing on to Harvard.

Harvard Campus Tour

Explore the Ivy League campus of the oldest college in the United States!

Our student tour guide started off by saying, “There are only three things you need to know about Harvard: Harvard is very old, Harvard is very rich, and Harvard is terrible at pulling pranks.”

You’ll walk around Harvard Yard, see the John Harvard statue, the exterior of the freshman bulletproof dorm, and the oldest building on campus.

Your guide will tell stories of student life as well (ours was a Philosophy major), and walk you past some of the famous houses of Harvard, where the non-freshman undergrads live.

Our guide showed off Lowell House, which has previously been home to author John Updike, Supreme Court Justice David Souter, actress Natalie Portman, and actor Matt Damon.

There’s a definite sense of gravitas that comes with touring a college campus that’s been around for over three centuries. Lots of name-dropping and impressive buildings funded by alumni.

We stayed in the area for a bit after our campus tour, choosing a couple of museums for our next stop.

Peabody Museum of Archaeology & Ethnology

Harvard-sponsored research trips have yielded some unique and very detailed exhibits for the Peabody Museum.

Each floor had something different: Native American cultures, the history of anthropology in the United States as seen through the Worlds’ Fairs, and Mayan culture, during our visit.

It wasn’t a huge museum, but it was all fascinating to me.

The Peabody connects to the Harvard Natural History Museum, so we seamlessly continued into those exhibits when we were done at the Peabody.

Harvard Natural History Museum

Before big national museums were a thing, colleges and universities created collections from their professors’ studies. That’s what you’ll see here.

The early taxidermy work is a bit jarring in some cases, but there are a lot of cool animals to see.

I thoroughly enjoyed the shark exhibits, but there were also dinosaur skeletons, geology, and a glass flowers exhibit before the main (enormous) taxidermy collection.

The botany exhibit with the glass flowers was very unique. Some of these I honestly couldn’t tell were made of glass. They looked so realistic with textures and everything.

You can see everything in this museum pretty quickly, making it and the Peabody a perfect afternoon stop before heading back downtown to the harbor for a sunset cruise.

Sunset Harbor Cruise

See the city from the water at golden hour while you sit back and relax on a Boston harbor sunset cruise.

Boston’s history started with the importance of its port, and your captain will share a bit of history while also pointing out the various famous buildings in the downtown skyline.

It’s a nice way to get off of your feet and enjoy a different perspective of the city before dinner.

Prudential Center Observation Deck: The View

I love seeing cities at night, all lit up. Even during the day, seeing a city from the top of a skyscraper is just a cool experience.

But, normally, I wouldn’t pay $40 per person for 15-20 minutes of views. I came here only because it was included in my Boston GoCity Pass and I didn’t have to pay extra to see it.

The views are stunning from the Prudential Center’s 52nd floor, an enclosed space but with raised viewing platforms.

If you want to feel the breeze in your hair, hop down a floor to the Cloud Terrace, an open-air deck with a bar and restaurant.

Walk around the perimeter and see all the Boston sites from above: Fenway Park, the Charles River and MIT, Boston Common, and the State Capitol.

Viewfinders will help you identify what you’re looking at.

Good to Know: It’s very difficult to take photos at night with a DSLR without getting a glare in the shot.

Tripods aren’t allowed, either, so I hope you have a steady hand. Phone cameras will work if you put them right up against the glass.

Optional Day 2 – Day Trip to Salem

The Boston GoCity Pass includes several of the big tourist sites in nearby Salem, Massachusetts. If you’re more into history than college campuses or food tours, a day trip to Salem is a solid option for your 2nd day in Boston.

Take the T out to Salem in the morning. It’s a small, walkable town so you don’t need a car to get around.

Good to Know: Salem has a hop on, hop off trolley tour, too! It’s not included in the GoCity Pass, but the entry fee to several of the sites on the trolley route are included.

While visiting Salem in October is the peak of all things witchy and fun, it’s never a bad time to see Salem.

Here’s what I’d see at a minimum if I visited with a GoCity Pass.

Salem Witch Museum

Salem’s unfortunate claim to fame is the infamous Salem Witch Trials of the 1690s. Hysteria gripped the area, and 19 people lost their lives in sham witchcraft trials.

There are several witch museums in Salem, all of them cheesy but also all mostly accurate. Just don’t expect this to be a museum with exhibits and historical artifacts.

It’s worth a visit once for the experience.

Large tan stone building with crenellated roofline and large cathedral windows houses the Salem Witch Museum. A white tarp out front protects visitors from the elements.

Peabody Essex Museum

An art museum with quite a lot of history mixed in, tucked into the center of town, the Peabody Essex has a lot of Asian artifacts in particular, thanks to early trading routes connecting Boston to the Far East.

One of the most impressive exhibits is a complete 200 year old Chinese home, deconstructed, shipped overseas, and rebuilt on the grounds of the PEM.

Headstones at Old Burying Point in Salem, MA with a large green tree and red building in the background

The House of the Seven Gables

The actual house from Nathaniel Hawthorne’s book of the same name. Built by a Salem merchant in the mid-1600s, there’s a lot of history here besides its link to Hawthorne.

Take a guided tour of the house, and then explore the grounds at your own pass.

Real Pirates Salem

A great spot for kids that love pirates! The museum includes honest-to-goodness pirate treasure recovered from a wreck, so you get to see real pieces of eight, cannons, and other artifacts.

If you’re tired of all the witchy themed sites, this is a good palate cleanser.

Trip Savings & Cost Breakdown

I’m all about the math when it comes to sightseeing passes. Here’s the cost breakdown for my 2 Day Boston itinerary, if I had paid for each activity individually.

ActivityCost Per Adult
Day 1 
CityView Hop on, Hop Off Trolley tour $ 82
Paul Revere House $ 6
USS Constitution Museum $ 15
USS Constitution (ship tour) FREE  
Walking History Tour $ 17
Old Statehouse & Old South Meetinghouse $ 15
Day 2 
MIT Tour $ 22
Harvard Tour $ 22
Peabody Museum of Archaeology & Ethnology $ 15
Harvard Museum of Natural History $ 15
Boston Sunset cruise $ 55
View Deck Prudential Center $ 30
Total Weekend Costs$ 294
Costs for Activities without a GoCity Pass

The Boston GoCity 2 Day All-Inclusive Pass currently costs $124 per adult.

Even if you did half of the activities on this itinerary, the pass would still pay for itself.

The Verdict: The Boston GoCity Pass paid for itself and then saved me an extra $170 compared to buying each activity individually without a pass.

Tips for a Weekend in Boston on a Budget

Boston is easy to visit on the cheap. Boston Logan International Airport is one of the country’s busiest airports, and it serves a lot of airlines so cheap flights are usually easy to find.

Here’s how I kept costs down on my whirlwind weekend in Boston.

  1. Book a hotel/rental within walking distance of a T stop.
  2. Use the T and walking to get around. No Ubers, no rental cars.
  3. Use a GoCity Pass to narrow down what to do and limit spending on activities.
  4. Choose your weekend wisely. Fall and summer are busy, but so is St Patrick’s Day weekend.

Is a Boston GoCity Pass Worth It for 2 Days?

Yes, everything on this itinerary is covered by the Boston GoCity 2 Day All-Inclusive Pass. It’ll save you over $150 compared to paying for these same sites individually!

If you’re an adventurer that likes to do a lot each day, then a GoCity Pass is always worth it. I’ve used them in multiple cities and always got my money’s worth.

Happy travels!

Headshot of Rachel Means at Clingmans Dome in Smoky Mountains

About the Author: Rachel Means

With six-figure student loan debt and only 10 PTO days per year, Rachel started traveling the world. A decade later, she’s paid off her loans, changed careers, and been to 38 US states and 17 countries. She’s an expert at planning and budgeting for travel and loves to help others do it, too! Read her full story here.