How to Spend Three Days in Boston, Massachusetts

fenway park

Despite both growing up on the East Coast, neither Alex nor I had ever been to Boston. We’d talked about going from time to time but it just never happened. So when we received an invitation to a wedding in Connecticut over Memorial Day weekend, we turned the trip into a longer one to include some time in Boston!

Day One

We landed late morning in Boston after a super early flight, took a Lyft 20 minutes into the city, and checked into our hotel, The Godfrey. While it definitely wasn’t a budget hotel, everything in the city was pretty pricey for at least that particular weekend (psh, Memorial Day) and we got a decent deal through (check out Why We Love

All that travel really worked up our appetites so our first stop was Sam Lagrassa’s, a sandwich shop about a 10-minute walk from The Godfrey. Omg it was so good. We arrived toward the tail end of lunch hour and there was a line about 10 people deep, but it moved quickly. Place your order at the counter, follow the line along until you reach the other end, then order any drinks and extras. Grab your number from the cashier, stake out a spot in the open seating eating area, and wait for your food to be brought to your table. Then dig in to your Cuban (if you’re Alex) or your grilled portobello and cheese (if you’re me). And don’t forget the fries!

sam lagrassa's sandwiches

Fueled up, we walked a few blocks over to Boston Common to get our bearings and start our adventure along the Freedom Trail. The Freedom Trail is a great way to explore Boston and see all the main sites – you can do it all at once, like we did, or break it up over a few days which would be more manageable for those not up for walking the entire thing at once.

Two and a half miles, four hours, 17 sites, 250 years of history, and countless churches, cemeteries, and parks later, we arrived at Bunker Hill Monument…and then turned around and walked the same distance back to our hotel. We like to walk! Don’t worry, on the way back we stopped at Union Oyster House, America’s oldest restaurant, to rest our feet and have a couple of drinks.

After a bit of down time back at the hotel, we emerged as the sun was starting to go down and set off for some Italian food in the West End. We landed on Antico Forno. I’d read about it in an article listing the best restaurants in the West End, and while it was good, maybe we were spoiled by our time in Italy? We weren’t blown away by the food but enjoyed the meal; we shared an Amalfitana pizza and the gnocchi di patate.

All day long we had seen boxes for Mike’s Pastry, which we learned was a cannoli shop in the West End, so since we were in the area we figured we might as well try some. However, when we got there we discovered it was cash only and as typical millennials, we never have cash. Modern Pastry was just down the street so we tried there next, but it was also cash only! Neither of us were interested enough to go to the ATM so we called it a night and ambled back to our hotel sans cannolis.

Day Two

We don’t ALWAYS go to SoulCycle when we’re on vacation…but we did on this trip. It was a nice morning walk through Boston Commons to get to the Beacon Hill studio, and on our way back, a family asked us for directions as if we were locals! Even better, we actually knew what to tell them. Love it.

After showering, we went for breakfast at Thinking Cup, a cute little coffee shop right along Boston Common. Alex had a sausage, egg, and cheese sandwich while I enjoyed their breakfast burrito, hold the meat, and a latte. It was a great spot and I wish we’d had more time in town so we could have gone back!

After breakfast, we set out for the New England Aquarium. We saw a lot of cool animals, including seals, turtles, penguins, myriad different fish, seahorses, really cool jellyfish, and an octopus (don’t make our mistake; follow the signs and you’ll find the octopus in the tank right before the elevator…don’t get in the elevator because the octopus is not in it). We had the aquarium/IMAX combo ticket which also got us entry into a really fantastic IMAX movie about the Galapagos Islands. We learned so much! And of course, now I want to go there.

Obviously (or here’s your reminder) don’t go to an aquarium expecting it to be a relaxing, quiet experience where you can be one with all the fishes and penguins. There’s a million kids running around and just as many oblivious parents shoving their kids up against the glass so you can’t see anything at all. Patience is the only virtue that matters at the aquarium. You’ve been warned.

TBH I’m a little iffy on aquariums and zoos but I really appreciated all the information the Boston Aquarium presented about its work to protect and conserve our oceans. And I can also appreciate how having a place – like an aquarium – where people can see the animals that need our protection helps to raise awareness about conservation in a more tangible, relatable, less abstract way and hopefully has more of an impact. 

What’s a trip to Boston without a lobster roll? In a cruel twist, given that we had just been at the aquarium, we decided on a late lunch at Neptune Oyster, figuring if we hit it around mid-afternoon, we wouldn’t have to deal with much of a wait. WRONG-O. At 3pm on a Friday there was a two-and-a-half-hour wait. I don’t even know where all the people were who were allegedly waiting. Also, the restaurant is tiiiiiny. There’s a bar that seats maybe 12 people, and then there are a few tables that can be moved and configured as needed but seat 16 people max. Anyway, we were not going to hang around in the street for two and a half hours so Alex Googled other lobster roll hot spots and this place Pauli’s popped up…which turned out to be right next door to Neptune Oyster. Jackpot. It was really good! And now I can say I’ve had a lobster roll. I got my mine cold with mayo, Alex got his hot with melted butter.

A quick search for “brewery Boston” told us that Harpoon Brewery was just a couple of miles away, so we got a Lyft and spent the rest of the afternoon there. We were pretty surprised at how busy it was…again, it was only mid-afternoon on Friday, but we lucked out and found two seats in the beer hall looking into the brewery area. The tour schedule didn’t align with our timeline but we were happy to drink our flights and people watch.

And then it was time for the main event: Red Sox vs. Braves at Fenway Park! Before going into the stadium, we picked up some fan gear then had a drink at a random sports bar – don’t remember the name, but it was bustling with people and had the cheap beer we had been expecting.

fenway park

Game time! We stuffed ourselves on pizza, peanuts, and beer while squeezing ourselves into the tiny, 100-year-old seats and enjoying a beautiful night in America’s oldest baseball park. The night ended with a 6-2 W for the Sox!

Day Three, Part One

We had a lazy Saturday morning, our main agenda item being finding a good brunch. Explorateur‘s menu and proximity jumped out at us and it did not disappoint. Alex was doing the searching which was good because I likely would have been turned off by its 3-star rating on Yelp. There was nothing 3-star about it! The space itself is really cool, kind of a French chic meets California cool. We started with the Explorateur donuts then moved on to the croque madame and the avocado toast (I’ll let you guess who got what). I also had a really good, and large, latte.

Following brunch, we packed up, checked out, and grabbed a Lyft back to the Boston airport to pick up our rental car.

Tip: When renting from Avis, join their Avis Preferred club. It’s totally free and you get to skip the line when picking up your car (or you go to a separate pick-up spot entirely).

When we got to the main Avis line, there were – no kidding – probably 40 people waiting and it was moving at a snail’s pace. It was worse than any security line I’ve seen in at least five years. After Alex signed up for Avis Preferred from his phone, we went to the Preferred counter and were in our car in less than 10 minutes.

At this point, we left Boston and drove to Simsbury, Connecticut for the wedding. 

Day Three, Part Two

Wedding festivities over, we turned the car around and drove back to Boston for the afternoon before our evening flight.

We got back to the Boston area mid-day and decided to spend the afternoon exploring Harvard and Cambridge.

I’m glad we did it, but it wasn’t really what either of us had expected. Probably from the telly and movies, I was expecting a quiet and quaint town anchored by a small and beautiful university. What we found was a pretty busy town and a very large school (I had no idea 20,000 students go to Harvard) that, despite having a pretty quad area – Harvard Yard – was pretty spread out. All the parking around campus was residential or permit only so in the end we parked at Whole Foods, bought a snack, then walked about a mile to Harvard Yard. Only then did we learn that graduation had been that weekend, so there was quite a bit of graduation infrastructure (tents, folding chairs, trash, visitors) still around. Who has graduation on Memorial Day weekend?

harvard yard

Perhaps if we find ourselves in Boston in the future, we’ll take another visit out to Cambridge to catch it in school mode.

Boston trip coming to a close, we left Cambridge and drove the 20 minutes to the airport to drop off our rental car and make our flight home to Austin.

What should we do the next time we’re in Boston?

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