Boston Travel Guide: What To Do When You Only Have 48 Hours

I’m currently sitting in my Boston hotel lobby. My friends’ flight to Atlanta is about to take off and mine isn’t for a couple more hours. Have you ever had such a good trip, you wished you had more time in the city to explore? That’s how I’m feeling right now, so I thought I would share a quick Boston travel guide with you.

The main reason for this trip was to see the Alanis Morissette album-turned-musical Jagged Little Pill and it did not disappoint (me, that is, but more on that later). Aside from paying homage to 90s angst, we of course wanted awesome food and to explore the city a bit.

Boston Travel Guide: Places to Eat

Saltie Girl

This place was a recommendation from an Instagram friend and truly had it all from killer décor – can you say mermaid style?! – to the best seafood and a generally trendy vibe. The music is loud and there are only maybe 6 or 7 tables – but don’t worry, if there’s a wait, you can head to the bar next door for a drink.

I was dying for a bowl of clam chowder and was shocked to see it was $18. How can soup be so expensive?! Not going to sugar coat it – this place will definitely hurt your wallet – but it was so worth it! Gorgeous bowl of the cream based soup with roasted potatoes, olive oil drizzle, and so many clams. The lobster roll was also insane.

Lolita Tequila Bar

This stop was a total fluke. Friends have 30 minutes before they leave for the airport. We’re about a 10 minute walk to the hotel to grab their bags and we see a patio bar on the water from across a bridge. Sure, let’s check it out. Why not?

Of course the airport early bird in me was having a near panic attack, but I always figured they could leave and I could finish up and pay the bill if necessary. Not necessary. We told our waiter the situation and in 20 minutes we had guava margs, guacamole, queso, and a really interesting take on a quesadilla. AND we had paid the bill and were walking out. I wish we had more time to linger here and try other stuff!

South End Buttery

We were trying to decide on a brunch spot Sunday and one of my friends said “I went to this really awesome place when I was here last year.” She looked it up on her bank statement and we were on our way.

We sat at the bar and had the best time chatting with the bartender over mimosas and amazing food. I had eggs benedict on a buttery biscuit, one friend got the egg sandwich, and another steak and eggs. Not a bad item between the three.

Boston Travel Guide: Things to Do

Beacon Hill Neighborhood + Acorn Street

Remember how I said our bartender at South End Buttery was awesome? I complimented her necklace and she told us exactly where to get it and recommended some other shops in Beacon Hill to check out. We all decided if we were to ever move to Boston, that’s where we’d live.

She also totally appreciated my Instagram love and sent us to Acorn Street which is an old cobblestone street hidden in the neighborhood. It was v. Instagrammable, but not exactly quiet – lots of people there with the same idea …

Median Brewery

The actual name of this is Trillium Garden on the Greenway, but it caught our attention because it’s an outdoor patio brewery (wine too) built in the median (greenway) of Atlantic Avenue. We only stayed there for one drink, but it was so pleasant and looked like it would be even cuter in the evening with string lights and cool weather.

Explore Campus

The musical was at a teeny-tiny theater on Harvard’s campus in Cambridge. It was a short Lyft from the city and I think we all wish we had more time to bum around and check out campus. As it was we had a quick drink and some nachos at Filipe’s Taqueria – which I found out has a location now in my old college town!

Go On A Boat

Given our short stay, we knew an organized tour would help us cover a lot of ground fast. Enter, the duck boat. What we didn’t realize was that with Boston being relatively condensed, we had already seen a lot of it. And the duck boat is not the most pleasant boating experience. Instead, I’d recommend finding a different REAL boat tour. We got to see the city from a totally different perspective – Beacon Hill is an actual hill – and see all the sailboats go by.

Head Out of Town

I struggled with this one since we were in town for such a short amount of time and I really wanted to see Boston more. My desire to check another state off my list (Rhode Island) outweighed in the end and one morning I woke up early and jumped on an Amtrak out of town. If you’re in Boston for more than a couple days, it might be fun to look at what day trips you could take to a neighboring city!

Back to Jagged Little Pill

My best friend’s husband and I bonded over this album years ago and were the two really pushing for this trip. Jagged Little Pill is my all-time favorite album and I went in knowing it would be a heavy story line. But, heavy was an understatement. It was truly depressing and therefore got mixed reviews from our crew. The best part was characters calling out the obvious misuse of the word “ironic.” Unfortunately, this musical is only programmed until July, so hopefully they’ll bring it back in the future.

Have you been to Boston recently? If so, what should we add to our list for the next trip?