2.5 Weeks In & Around Boston: Here’s What We Did

In mid-September we stayed five nights in downtown Boston then, after spending a month in Maine and Vermont when my parents came to visit from the UK, we returned to the Boston area for almost two more weeks.

We crammed as much as we could into our five days in downtown Boston to maximize our hotel’s location, but took things a bit easier for the two weeks on the outskirts of the city as Shae and I were both so exhausted from being on the go with my parents for a month (I don’t know how they kept up!).

Here’s a roundup of everything that we did during those 2.5 weeks.

Where We Stayed

Hyatt Regency Boston

There are two Hyatt Regency properties in Boston. One is downtown, while the other is at Boston Seaport near the airport – we stayed at the one downtown. Overall we had a great stay, with one of the hotel’s biggest selling points being its location. It’s nice and central to everything, plus it’s only a couple of blocks away from the beautiful Boston Common.

We redeemed a suite upgrade award ahead of time which meant that we were able to lock in a one bedroom suite there. That gave us much more space and comfort which was nice seeing as we were there for five days.

While the buffet breakfast wasn’t the most expansive of buffets, it still had a great selection of food. I also appreciated that the melon and pineapple were perfectly ripe (that’s never a given with hotel breakfasts) and they had some decent pastries and croissants in addition to the various hot options.

You can read my full review of the Hyatt Regency Boston here.

Hyatt House Boston/Waltham

We had to redeem 20,000-23,000 World of Hyatt points per night for our stay at the Hyatt Regency which is more than we’d usually redeem for hotel stays. Seeing as we wanted to spend another couple of weeks in the Boston area in mid-to-late October, staying at the Hyatt Regency wasn’t going to be an option as that would’ve cost 250,000+ Hyatt points.

There was another good Hyatt option in the suburbs though. The Hyatt House Boston/Waltham is almost 20 miles west of downtown Boston, so that meant its points price wasn’t as high. Rather than having to redeem 20,000-23,000 points per night, we only had to redeem 8,000 points per night for the 12 nights that we stayed there. We had even more suite upgrade awards to use up, so we applied two of those (each one is valid for a stay of up to seven nights) in order to get a one bedroom suite with a full kitchen.

We had a good, albeit unremarkable, stay there. Breakfast is complimentary for all guests and includes several hot options, fruit, cereal, bagels, etc. There are guest laundry facilities, a fitness room, etc., so it’s a decent enough place to stay. The downside is that it can take a while to drive into downtown Boston from there depending on the traffic, but we knew that going into it.

What We Did

Samuel Adams Brewery Tour

Shae and I first visited Boston back in 2011 or 2012. We were there for an event, but had a little time for ourselves and so we decided to do a Samuel Adams brewery tour. Seeing as it had been more than a decade since we’d done that, we decided to go and do it again.

While Sam Adams isn’t my favorite beer, it’s a fun experience that’s worth doing during a trip to Boston if you like beer at all. You get to try a few different beers on the tour, one of which was their Oktoberfest which had been aged in Jim Beam barrels for a couple of months.

Boston Freedom Trail

The Boston Freedom Trail is a 2.5 mile long trail running through downtown Boston which takes in many of the city’s key sites from history. That includes Bunker Hill, Boston Common, the Paul Revere House and much more.

It’s not just some nebulous route where you need to carefully follow a map to ensure you don’t make a wrong turn. It’s worth having the map up on your phone so you know which buildings are around along the way to help ensure you don’t miss seeing anything, but the route itself is marked by a non-stop brick line on the sidewalk and across roads.

The Freedom Trail is a fantastic way to explore the city, so it’s definitely worth doing, even if you don’t stop at every single site along the way. You can read more about it here.

Boston Tea Party Ships & Museum

The day after my parents arrived we visited the Boston Tea Party Ships & Museum before moving on to Maine. Shae had visited with a friend several years ago and thought it was a fun experience, so with me and my parents all being British and tea drinkers, it seemed like an appropriate place for us to visit (despite the history!)

I can see why Shae had enjoyed the tour so much. The tour guides are all dressed up as people from the 1700s and really lean in to their characters. They’re a lot of fun, get audience participation during the tour and provide a decent amount of history in a fun and enjoyable way. It’s one of those kinds of tours that’s fun for people no matter how old you are, so this is something else that’s definitely worth doing when visiting Boston.

At the end of the tour you can add on a tea tasting experience in Abigail’s Tea Room where you can get bottomless tea from five different varieties – the same kind of blends that they had back in the 1700s.

Boston Common

One of my favorite things to do when staying downtown was walking around Boston Common. Boston Common is a 50 acre park that’s been around since the 1830s. It’s a lovely space to walk around or relax.

It’s also home to The Embrace, a bronze sculpture dedicated to Martin Luther King, Jr. and Coretta Scott King which was unveiled at the start of 2023.

Beacon Hill

Most of the exploring we did was on the Freedom Trail, but we also checked out a few other parts of downtown. One of the best of those was Beacon Hill, a quaint part of the city with tall brick buildings.

Perhaps its most iconic street is Acorn Street with its narrow cobblestone road running down it. It’s apparently the most photographed street in the US and was also the setting of a graduation photo shoot the day we visited, but we managed to get an empty shot once they were done.

Beacon Hill is also where the Massachusetts State House is located.

Switchfoot Concert

OK, so it wasn’t in Boston, but it happened while we were staying there. Switchfoot toured this fall to celebrate the 20th anniversary of their The Beautiful Letdown album, playing the entire album during the concert in addition to many of their other songs.

I’d seen them live a couple of times before and they’ve always put on an amazing show, so I didn’t want to miss out on this. For my birthday this year I got a ticket to see them live which also included a pre-concert meet & greet. I think they were playing in Boston while we were actually there, but the venue they were playing at seemed to have weird seating arrangements, so I got a ticket for where they were playing in Connecticut seeing as that was only about 1.5 hours away. It was another fantastic concert and I was pleased that I managed to time this shot perfectly!

Where We Ate & Drank

Samuel Adams Brewery

In addition to the brewery tour – or even if you don’t go on a tour – you can grab a drink from their bar. It was a nice day when we visited, so we sat on outside on their patio enjoying the live music.

Bearmoose Brewing Company

Sam Adams wasn’t the only brewery we visited (surprise!). We stayed in downtown Boston just after finishing up in Wareham which is only an hour or so away. We had to be out of the Vacasa property in Wareham by 10am on our day of checkout which was likely going to be too early for us to be able to check in at the Hyatt Regency.

We had to stop by a storage unit to leave most of our belongings there for a month so that we could fit my parents and their cases in the car with us (they were arriving a few days later). Despite pretty much everything we own fitting in our 2004 Toyota Corolla, it turns out that we have a lot of stuff that we can live without for at least a month!

We finished up at the storage unit at about 11:30am. It was a dreary, damp, somewhat chilly day that day, so we weren’t keen on killing time outside at a park or something like that. We therefore looked up pet-friendly breweries, wineries and distilleries. Most of the ones we found that were pet-friendly were only pet-friendly out on their patios which wasn’t appealing due to the temperature and weather. It also seemed like most eateries and drinkeries in downtown Boston aren’t pet-friendly at all – I think there might be some kind of regulations or bureaucracy which limit that.

Thankfully we did discover one brewery north of downtown Boston that allowed dogs inside – Bearmoose Brewing Company. We arrived just as they were opening and so were the first people there, but a brewery tour bus arrived shortly afterwards which added some atmosphere.

Shae was happy to drive the short distance into downtown Boston after that, so I got a couple of beer flights while we were there. I got different beers each time in order to try more of them, with the exception of their Oh My Gourd which I got on both flights as I liked it so much. That’s a pumpkin spice beer where they coat the glass’s rim with caramel and then dip it in something like cinnamon sugar – delicious!

City Winery Boston

City Winery has several locations around the country and we’ve been to the ones in St Louis (excellent) and New York (OK) as we have a bunch of referral credits earned in the inKind app. We still have loads of those to use up, so we visited City Winery in Boston a couple of times while we were there – once when it was just Shae and me and then with my parents just before they flew back home.

We had an enjoyable time both times. It was better than our experience in New York, but not quite as good as that first time in St Louis. The first time we visited the Boston restaurant it seemed like the dishes are served tapas style. We figured that meant they’d be small portions, so we each ordered four dishes each – that’s a big mistake unless you don’t mind taking some food home with you! The portion sizes were larger than we were expecting, so there ended up being far more food than anticipated.

Here’s some of what we ordered – I think Shae liked the hanger steak most of all, while my favorite was the lox n’ flatbread.

Hei La Moon

We had a couple of Grubhub credits to use up too, so we ordered General Cheung’s Chicken from Hei La Moon. The chicken was decent, but we hadn’t realized it didn’t come with rice. Thankfully we had some wraps that we ate with it.

Mike’s Pastry

While walking along the Freedom Trail we spotted lots of people carrying string-lined boxes from Mike’s Pastry.

They’re most well-known for their cannolis, with something like 20 different flavors available. That’s not all though – they have a huge array of other pastries.

There’s no way we were going to pass up on an opportunity for some delicious pastries, so we got a few to try. I was a little disappointed as I hadn’t realized until later on that they’d given me the wrong type of cannoli (I’d wanted a chocolate cream filled one), but the pastries were all tasty nonetheless.

What We Missed

Although we spent quite a bit of time in the Boston area, there were still quite a few things we didn’t get to – here’s a list of future things to do in Boston. Some of these are based on our own research, while others are suggestions from friends and readers.

• Hop on, hop off trolley tour
• Boston African American National Historic Site
• Museum of African American History
• The Bell In Hand Tavern – has a Sam Adams beer you can’t get anywhere else
• The Paul Revere House – we stopped outside while on the Freedom Trail, but didn’t go inside
• Boston Public Library – Central Library
• Rock City Pizza
• Millers River Potato Monument
• Charlie’s Kitchen for chicken wings
• Bagelsaurus
• Franklin Park Zoo – breakfast with sloths
• Boston Pops