Boston Travel Guide

Acorn Street in Beacon Hill

I first came to this badass city for a Foo Fighter’s concert at Fenway in 2015 and since then I vowed to return for a proper vacation. Six years later, I finally made it back! It absolutely lived up to the hype. It’s a city that is rich in history and full of beauty. There is so much to do in Boston and the surrounding New England areas that I tried to cram as much as I could during my long weekend trip (Maybe a little too much). I visited the last weekend of September and actually got a taste of what fall feels like. The leaves were just beginning to change and the highs for the weekend were 72 degrees. I took advantage and walked 33 miles over the course of the trip! Boston really is the GOAT for walking. Their subway, the “T”, is fairly easy to navigate, but if you’re in town and its good weather, just start walking. Their downtown is compact and because of this, sometimes it’s faster to walk to your destination than to wait for the subway. Beacon Hill, Cambridge, and Seaport were my favorite neighborhoods and I wish I had more time to explore there. If you’re into picturesque Northeastern views, breweries, and Revolutionary history, Boston is a must visit. It’s the city of firsts – the country’s first subway station, the first public park, the first public school, and the county’s oldest institution of higher education, Harvard. Fun fact (not really), the city of Boston banned happy hour due to the death of a woman from drunk driving in 1984.

Boston Itinerary:

First night: Walked from my hotel to the Seaport neighborhood. Pre-gamed at Cisco Brewers and people watched until my reservation was ready at Row 34. I had the best lobster roll of the trip at this swanky restaurant. I also happened to sit next to a couple at the bar and the guy has family from both sides from New Orleans. Such a small world. He ended up telling me about this whole in the wall place in Cambridge that serves some of the best lobster sandwiches.  One of my favorite parts about traveling is meeting people you share a connection with and getting recommendations for a place you would never have found through research or stumbled upon.

Second day: The plan was to go to The Friendly Toast for breakfast but I couldn’t get a reservation :/ So I decided on Mike & Patty’s. I got within a block from the restaurant and the smell hit me like I was in a cartoon. I instantly knew I made the right choice. It was the best breakfast sandwich I have ever eaten. It’s a small place and doesn’t have seating but you can walk across the street and eat your breakfast on a bench and just soak up the neighborhood. Before I started the Freedom Trail I needed a little extra push so I went to Thinking Cup for coffee. Then I walked through the Boston Common and hopped on the trail.  The Freedom Trail is a 2.5-mile trail that starts in Boston Common and ends at the Charlestown Navy Yard. You simply follow the brick marking on the pavement, and watch for signs and historical markers. Take your time and make this the main activity of the day. Some of my favorite stops were:

  • Boston Common– America’s first public park, created in 1634
  • Massachusetts State House (You’ll know it when you see the gold dome)
  • Park Street Church – Played a major role in the abolitionist movement
  • Granary Burying Ground – Samuel Adams, Paul Revere, John Hancock, the Boston Massacre victims, and Ben Franklin’s parents are all buried here.  This was my favorite stop on the trail. There’s just something cool about standing above where some of our founding fathers are buried and seeing tombstones built in the 1600’s.
  • Old State House – Where Samuel Adams uttered the famous phrase, “No taxation without representation!”
  • Boston Massacre Site
  • Faneuil Hall Marketplace – Housed many meetings that led to the Boston Tea Party
  • Paul Revere House ($6 admission)
  • Old North Church – Its steeple was used to signal the arrival of the British
  • Copps Hill Burying Ground
  • Bunker Hill Monument
  • Charlestown Navy Yard – USS Constitution, our country’s first war ship, used in the War of 1812

After that I was completely gassed and had to carb up at Night Shift Brewing @ Lovejoy Wharf. Their IPAs were the best of the trip. For dinner I headed over to Shojo for their Wu-Tang Tiger Style Ribs and Kimchi Fried Rice. Which was then followed by a nightcap at Trillium Brewery in Seaport.

Third day: I tried to take it a little easier today and utilize more of the subway to save my legs for the hiking in Maine. But first I had to head over to Acorn Street in Beacon Hill. Once home to John Adams, it’s one of the most picturesque neighborhoods with its cobble stone streets. You actually feel like you’ve been transplanted back in time. Then I made the short walk to the Charles River Esplanade to take in the beautiful view of the Charles River and to do some people watching. This is a great vantage spot to see Cambridge and the Longfellow Bridge. Right across the river in Cambridge is Charles River Canoe & Kayak, where you can rent a kayak and paddle down the Charles River to Kendall Square. From there you can walk down Broadway Street and stop at Graffiti Alley (Street art is always changing) and Lamplighter Brewery on your way to Harvard. I was slightly hungover and in a rush to catch the Saints Patriots game so I didn’t get to kayak. Instead, I headed over to Cambridge Common and Harvard Square after the Charles River Esplanade. Walking back from Harvard I stopped at Alive & Kicking Lobsters (This is the place the guy at Row 34 told me to try) . If you’re not looking for it, you can easily miss it because it’s located on a residential street. Instead of lobster rolls they sell lobster sandwiches. I won’t put it ahead of the lobster roll at Row 34 but it’s still lobster and it’s delicious. I also tried clam chowdah for the first time here. My plan was to catch the Saints game at Lamplighter Brewery but they don’t have TVs :/ So I went back to Night Shift Brewery. I wasn’t complaining. Got to try more IPA’s and just a great atmosphere to watch a game. I then made my way to baseball’s Mecca, Fenway (If taking the subway, get off at the Kenmore stop). You can pregame outside the stadium on Jersey St. & Lansdowne St. I stumbled in the Lansdowne Pub. Great pub sliders. I can’t even put into words watching the Red Sox and Yankees play at Fenway. As a lifelong baseball fan, this was a major bucket list item for me and I’m very grateful that I got to cross it off. 

Fourth day: I think I was most excited about visiting Maine. It’s always been a bucket list item for me – the lobster rolls, hiking the Appalachian Mountains, the quietness, experiencing a real Northeast fall. I didn’t waste time since I was only there for the day so once I made the 2-hour drive from Boston I went straight to Wolfe’s Neck Woods State Park and hiked the Harraseeket and White Pines Trail (full disclosure, I didn’t hike the entire trail. My time was limited so I hiked along the shore) I really wanted to hike Bradbury Mountain so I could get a bird’s eye view of the leaves changing but I didn’t think I would have time so I didn’t. Looking back on it I could have squeezed this out so if you end up following this itinerary DO IT! After the hike I headed to downtown Portland for lunch. Within 5 mins of being in Portland I saw two Kombucha shops, a mead distillery, and a guy playing guitar on the corner. Portland is exactly how I imagined it lmao. I ate at Duck Fat for lunch and even though I had to wait 45 mins it was worth it. Best poutine I’ve ever had and one of the best banh mi’s I’ve ever had. I read that Austin Street Brewery was one of the highest rated breweries (Fun fact – Portland has 16 of them) in Portland so I made the short walk over. Not a bad Oktoberfest. The guy I met at Row 34 suggested going to Allagash, Foundation, & Definitive Breweries because they’re all located on the same street. If you’re staying here for more than a day you should take his solid advice. My last stop in Maine was Portland Head Light and I could have easily spent half the day here. Just look at the pictures. Words do not describe the view. I ended this amazing trip at Myers + Chang for dinner. Couldn’t have picked a better last meal. Their egg rolls are fucking amazing.

  • Portland Head Light
  • Harraseeket and White Pines Trail
  • Longfellow House
  • Boston Common
  • Granary Burying Ground
  • Site of Boston Massacre
  • Paul Revere’s House
  • Bunker Hill
  • USS Constitution
  • Fenway Park
  • St. Charles River
  • Charles River Esplanade
  • Mike & Patty’s
  • Row 34

Where to Stay in Boston:

Cambria Hotel, Downtown-South Boston – Fairly affordable and not too far of a walk to Seaport. But if money is no option, definitely stay in Seaport.

Transportation in Boston:

Walk and ride the subway (Called the “T”) or Uber when you need a break. If you’re going to Maine just rent a car for the day. The subway is fairly easy to use. Just make sure you end up on the right side of the track. Some stops can be a little confusing so don’t be afraid to ask a subway attendant. No shame in that, I did it a couple of times. To ride the subway, you can pay $2.75 for a one-way ticket (tickets are available at every stop) or you can buy a Charlie Card (reloadable), where each ride is $2.25 and it includes free transfers to buses. You can also buy a one-day pass for $12.75 and a week pass for $22.50.

Tips for Visiting Boston:

  • From the airport you can take the MBTA silver bus (SL1) to the South Station for free. From the South Station you can hop on the red line or walk out of the station which puts you close to Downtown.
  • Use Reddit for recommendations. Search for whatever city you’re visiting, there’s usually a thread. This was the first time I used it to get recommendations and it was clutch.
  • It’s a WALKING city, wear comfortable shoes – I walked 33 miles in 3 days and that’s with Ubering & riding the T! The GOAT walking city in the US.
  • Always verify where you’re Ubering to before you order the ride.  I thought I was going to a brewery in a certain area but didn’t realize that brewery has multiple locations. I had to cancel the Uber mid-ride and when I got out of the car I was in a sketchy neighborhood (Mom, don’t read this).
  • Use the AllTrails app for the Freedom Trail.
  • Make restaurant reservations at least a week in advance.
  • Visit in October. I went the last week in September and the leaves hadn’t quite changed colors yet.
  • Carry an extra mask on you.
  • If you’re a history nerd, check out the Longfellow House in Cambridge. I visited this historic site on my first visit to Boston years ago. Not only did it serve as George Washington’s headquarters during the Revolutionary War, but it was also the home to the poet Henry Wadsworth Longfellow for fifty years.

Bucket List for Visiting Boston Again:

Boston Maps: