Got a work trip to Boston? Or maybe you stumbled upon this blog because you have a short, several-day stay in Boston? Either way, you’ve arrived at the right place!

Boston is a city close to my heart, having called it home for years. Its rich history, diverse neighborhoods, and lively atmosphere are hard to capture in a single post.

So you’re like to get the post right? Alright, alright. Here, I’ll be covering Beacon Hill, Fenway, and Cambridge. Also random, but I happened to be on this trip during the biggest rap beefs of 2024: Kendrick vs. Drake!

Getting to Boston

Arrival and Transportation: Upon arriving at Boston Logan Airport, you can get to your destination for free using Boston’s transit service, the Silver Line SL1. This service will take you from the airport directly to South Station. From South Station, you can catch the Red Line towards Alewife, and your recommended stop is Charles/MGH. This station is conveniently located near Massachusetts General Hospital and the Beacon Hill neighborhood, where the Liberty Hotel and nearby attractions are situated.

Fun Fact: The Silver line was originally supposed to be a train station but it ended up not being one and instead you can just imagine a tunnel being dug out for a train and now instead an electrified bus runs through the tunnel .

If your hotel doesn’t offer a shuttle, consider using the T to get to and from your destinations. Ubers and Lyfts are also readily available.

Gear Used

Essential gear that kept me going on my travels (disclaimer: contains affiliate links).

Accommodations

The Liberty Hotel: Located in the historic Beacon Hill neighborhood, the Liberty Hotel, a former jail turned luxury hotel, offers unique accommodations with a popular nightclub called Alibi, especially bustling on weekends.

While not part of the Amex’s Fine Hotels and Resorts program, the hotel offers several premium amenities. That means that if you want a later check out, say 1.30PM then they will work to accommodate you or if you want to extend the night and stay in the same room FYI–this wasn’t the case at the Omni in Nashville nor did they even bother to look this up. Of course, If your work is covering it and it’s attached to your Amex account then it’s a good deal.  

This location is a good launching point for exploration around the city or if you have meetings downtown or MGH/Longwood Medical Center. There is a free shuttle that goes from MGH to Brigham and Women’s Hospital and also to Mass General Brigham’s Headquarters in Assembly Row (an area that has a lot of fun spots). 

If that doesn’t work then you can simply catch an Uber or take the Red Line. However this does get complicated since if you want to go to a place that seems close in Boston you will have to take the Red Line back downtown to Park Street if you want to switch to the either hotel options on the Green Line or Orange Line

If you wake up and you actually want a little more for your breakfast, then I would recommend heading to Flour–which is a quick 5 minute walk. Here I would get the breakfast sandwich with bacon (for meat lovers) and without for vegetarians. This one is one of the better breakfast sandwiches I’ve had and I always used to get this especially when I would study at MIT and go to their Cambridge location here.

If you’re looking for a simple yet satisfactory option, consider Hotel 1868 in Cambridge, well-connected by the Red Line and competitively priced, especially for family visits to local universities.

Hotel 1868:

This hotel might be more familiar for those who have family enrolled at Lesley University but others might see it super far away. However, this hotel is situated right in front of the Red Line Porter T-Stop and has a Nero Café right next to it.

This is a rather low-frills hotel that has everything you need and is always competitively priced in my opinion. And if you visit there once, make sure to call in and use the discount code they provide since it offers a discount on your next stay. And the reason for calling is that websites such as Amex’s Travel Portal will show this hotel as having no rooms especially in high-season that’s why it always helps to call.

Tip: Calling Hotel 1868 directly can sometimes unlock hidden deals or repeat customer discounts. And don’t forget to use your American Express Platinum card to earn rewards on your booking!

If you need a fix for coffee just pop literally next door to Nero and get the coffee you need and if you want some breakfast items just make your way down the street to Bagelsaurus (however, you want to get there early otherwise there will be a line).

And if you’re on this side of the Charles River–you’re closer to Sommerville. In this case, I would check out Machu Chicken for Peruvian chicken and make sure to get the yellow and green sauce. Otherwise, you can venture a little further and check out Oliveira’s an all you can eat Brazilian Steakhouse and a great alternative to the over-popular Fogo de Chao. And if that’s not fitting the bill then you can check out Inman Square. And for breakfast head to a local classic S&S.

Beacon Hill: History, Luxury, and a Great Breakfast

Beacon Hill, with its charming cobblestone streets and historic architecture, is a great place to start your Boston adventure.

• Stay: The Liberty Hotel, a converted jail, offers unique accommodations with modern amenities and a lively atmosphere.
• Eat: Grab a delicious breakfast sandwich at Flour Bakery & Cafe, a local favorite just a short walk from the Liberty Hotel.
• Do: Explore the neighborhood’s charming shops and historic landmarks, or take a stroll along the Charles River Esplanade.

Fenway: Catch a Game and More

Fenway Park is a must-visit for any baseball fan. Catch a Red Sox game and experience the electric atmosphere. Even if you’re not a baseball enthusiast, it’s worth visiting the park for its iconic Green Monster and rich history.

• Eat: Grab a hot dog from one of the many vendors at Fenway Park, or explore the diverse dining options in the surrounding area.
• Do: Catch a concert or event at the House of Blues, or visit the nearby Museum of Fine Arts.

Make sure to at least stay until the bottom of the 8th inning to hear “Sweet Caroline” by Neil Diamond. If you want to know more about why this song is played, check out this article here. And of course, you will hear “Take Me Out to the Ball Game” during the 7th inning stretch.

If you’re seated in the bleacher seats near the bar area, you’re in luck—they often throw hot dogs to the crowd there. Here’s a tip: instead of trying to catch attention by jumping up, you can simply ask the hot dog vendor for a free hot dog.

Cambridge: Academia and Craft Beer

Cross the Charles River and discover Cambridge, home to prestigious universities like Harvard and MIT.

• Eat: Enjoy a casual meal at Russell Tavern in Harvard Square, known for its lively atmosphere and diverse menu.
• Drink: Explore the craft beer scene at Aeronaut Brewery, which offers unique brews and a welcoming outdoor space.
• Do: Stroll through Harvard Yard, visit the Harvard Museum of Natural History, or browse the bookstores and shops in Harvard Square.
• Tip: If you’re in town for Cinco de Mayo, check out the “Viva Central Block Party” for festive fun and free Modelo t-shirts.

Russell Tavern in Harvard Square

To experience Harvard Square and a popular spot, I’d definitely recommend Russell Tavern. I would definitely recommend sitting by the bar on the lower level where you can always interact with those around you, the bartender, and enjoy a view of the TV.

In our case, we happened to be there during the 150th Kentucky Derby won by Mystik Dan—and the lady alongside us gave a breakdown of what to pay attention to, mentioning that the horses have to run for approximately one mile. As for me, I know nothing about horse racing culture aside from Jack Harlow’s Churchill Downs song with Drake.

Apparently, her dad was very familiar with horse racing and could even tell which horse he would bet on based on the walk before the race.

In her case, she had two options, so of course, I had to root for those two:

• Sierra Leone with Jockey: Tyler Gaffalione (I found out this horse is worth $2.3 million dollars!) who placed 2nd. The jockey is now facing a hail of “cheating” allegations from spectators.
• Resilience with Jockey: Junior Alvarado.

I know very little about horse racing besides OTB betting or actually reading a really good book called Kick the Latch by Kathryn Scanlan that I picked up at Shakespeare and Company in Paris before it closed. But she did teach me a thing or two to make sure I can understand how to properly taste and enjoy a wine glass.

What I found ironic and an interesting takeaway is that these jockeys’ entire preparation comes down to 3 minutes, which is rather scary and impressive. Just think of how many things we do in life that require that amount of preparation and specialization.

Here’s what the jockey Brian Hernandez for Mystic Dan (Trainer: Kenny McPeek) said in a recent LA Times article: “That was the longest few minutes of my life I’ve spent waiting for them to hang the dang number up,” Hernandez said.

Such a level of preparation and prestige, along with the financialization (ad revenue, financial backing, promotion, and betting), boils down to just a few minutes in a highly televised event. I had to mention this more specifically before someone comes in here and starts mentioning stock and day trading or specific over-the-top surgeries like the loop electrosurgical excision procedure (LEEP).

I guess now I might have a slightly more elevated interest in horse racing with the upcoming Triple Crown—a callback to my previous days of horseback riding.

Oh yea! I forgot to mention what we got off the menu. Here’s the breakdown:

• Raw Bar:
  • Local Oysters: Served with cucumber mignonette and cocktail sauce. (You can get these individually.)
  • Crispy Rhode Island Calamari: Accompanied by pepperoncini, pickled fennel, tomato, capers, and basil aioli.
• Main Courses:
  • Russell House Burger: Cheddar, bacon, caramelized onion, special sauce, served on a sesame brioche. (My brother got this one.)
  • Bucatini Bolognese: A hearty mix of pork, beef, and veal with garlic crostini and grana tuile. (I got this and thought it was delicious!)
• Beverages:
  • Whalers | Rise (American Pale Ale – RI 5.5%): Features notes of citrus, pine, and malt.
  • Juggernaut, Pinot Noir (Russian River Valley, CA – 2020): Red fruits, lily, and toasted oak. (This was recommended by the lady I chatted with about the Kentucky Derby, she also mentioned the Pizzas are worth getting.)

Aeronaut Brewery

If you’re at Aeronaut, you can work up an appetite at the nearby bouldering facility or head straight in for some beers. I’d definitely recommend the following:

• Prototype – Batch #P542: This Rustic American Lager is “brewed w/ local valley malt gain & four star farms case hops,” as noted on the beer board.
• A Year with Dr. Nandu: An American IPA described as a “punchy pale ale loaded with centennial, mosaic & citra hops.”
• Mechanical Luchador: Since it’s also Cinco de Mayo, I have to mention this Mexican Style Lager, “pale, crisp light lager with notes of lemon & lime.”

Viva Central Block Party

If your extended work period in Cambridge overlaps with Cinco de Mayo, consider checking out the “Viva Central Block Party,” hosted by the Central Square Association. Located just behind Naco Taco in Central Square, this festive event offers free Modelo T-shirts, customized on-site with Boston branding, as well as elotes and other treats.

Boston Beer Trail: A Toast to Local Brews

Boston’s craft beer scene is flourishing, with numerous breweries offering unique flavors and experiences.

• Visit: Tour the original Sam Adams brewery in Jamaica Plain and learn about their brewing process. This brewery is easily accessible off the Orange Line at the “Stony Brook” stop.
• Explore: Sample a variety of craft beers at Harpoon Brewery, located conveniently on the Silver Line bus route from the airport. If you’re here in October, I’d definitely check out their Octoberfest.
• Relax: Enjoy a beer by the Charles River at Night Shift Brewing’s Owl’s Nest beer garden (weather permitting), and there is a Mini Pizzeria nearby if you get hungry. It’s a good place to stop if you walk along the Esplanade and watch the boats from the nearby Community Boating sailing club. If you wait on the dock and ask around, some people might ask you to come and help with tacking and jibing (that’s what happened last year, since I was eager to try what I learned from ASA 101).
• For the Adventurous: If you have a car, venture to Tree House Brewery for some of the most sought-after craft beers in the region.

Otherwise, I’d recommend experiencing a mix of draft beer and arcade games near MIT at Roxy’s Grilled Cheese Sandwich shop. You might be thinking, “Roxy’s, really?”

But hear me out!

You actually enter Roxy’s, go through the kitchen’s double doors, and it opens up to a vast Dave & Buster’s (Braintree)-meets-Lucky Strike (Somerville) combo that’s sort of an adult playground called Roxy’s Arcade. Here, you can enjoy boozy smoothies and plenty of draft beers, all just a short distance from your Boston or Cambridge hotel.

Returning to Logan Airport: When it’s time to leave, you can reverse your initial journey via the Red Line to South Station and transfer to the Silver Line SL1, which services all airport terminals. I was dropped off at Terminal A (which is Delta and WestJet). Remember to allow extra time if traveling during the weekend when the MBTA may schedule maintenance, potentially extending travel times.

The travel time to Boston Logan Airport can vary significantly depending on the time and day you choose. I traveled from Porter to Logan on a Sunday, and due to the MBTA’s typical weekend maintenance, it took 1 hour and 4 minutes door to door.

At the airport, the experience was somewhat expedited. Despite a queue at the baggage drop and the need for attendant support, it moved quicker than similar lines in Seattle. However, a minor hiccup occurred as they did not place a “Sky Priority” baggage tag on my luggage, which is standard procedure for quicker handling. The significance of these tags in expediting luggage delivery is often debated, as evidenced by discussions on FlyerTalk. Based on my experiences, the likelihood of “Sky Priority” tagged luggage arriving first is about 50/50.

Here’s a concise breakdown of my travel to the airport:

• Porter Square to South Station (with a bus transfer at Park Street): 1 hour and 4 minutes
• Delta Sky Priority Baggage Drop Wait Time: 3 minutes and 19 seconds
• TSA Precheck: 5 minutes
• Travel from TSA Precheck to Gate A15: 4 minutes and 39 seconds

However, despite the commotion, I snagged an upgrade to Delta Comfort. The perk of course is the Sweetwater Hazy IPA beer.

Additional Tips: Keep an eye on TSA wait times, which are generally shorter than many other airports but can vary. Consider the experiences of navigating these times and planning accordingly for a smooth departure.

Boston

Tips, Tricks, and Logistics

• Getting Around: Take advantage of Boston’s free public transportation system, the “T,” to get from Logan Airport to your hotel and explore the city.
• Accommodation: For a budget-friendly option near Harvard Square, consider Hotel 1868.
• Peak Season Travel: If you’re visiting during graduation season, be prepared for higher hotel prices. Book early and consider alternative accommodations like hostels or vacation rentals.
• Returning to Logan Airport: Allow ample time for your return trip to the airport, as public transportation can sometimes be unpredictable.

Trip Soundtrack

Because every adventure needs a soundtrack, each of my trips comes with a theme song. And for this trip's anthem? Well, it's...

Kendrick Lamar - Not Like Us

Boston may be hard to capture in a single blog post, but I hope this guide gives you a taste of what this vibrant city has to offer. Whether you’re here for work or pleasure, make the most of your time by exploring its charming neighborhoods, indulging in delicious food and drink, and experiencing its unique blend of history and modernity. Cheers to your Boston adventure!