Weekend in Boston – Walking the Freedom Trail

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On the front end of our big trip to Europe, we used our Southwest Companion Pass for a weekend visit to Boston with some friends (Hey Mel & Jay!)  Brooke had been to Boston before, but this was my first time.  I was excited to explore a new city, especially one with so much significance in American history… and bonus – it was St. Patty’s Day weekend!

Air Travel/Transportation

  • Southwest Airlines – 11,342 Southwest RR Miles + $11.20 total for both (using Companion Pass)

We booked this trip to Boston as a “positioning flight” for our award flight to Ireland.  Boston is the closest US city to Ireland, which allows us to take advantage of a sweet spot in British Airways’ distance-based award chart (more info here).  We used our Companion Pass to cut the point cost in half, and as always, Southwest provided a very pleasant flight experience.


  • Westin Copley Place – 12,000 SPG Points per night x 2 nights

After quite a bit of research, we decided to stay at the Westin Copley Place in Boston’s Back Bay area.  This hotel was conveniently located within walking distance from most of the sights we wanted to see.  It was also very close to a train station, giving us easy transport from/to the airport and up to visit the Harvard campus.


The hotel itself was quite nice, with a trendy, modern design.  We booked a double queen room to share with our friends, and we scored a fantastic view of the river!  The room was spacious enough for four adults to share, without tripping over each other’s stuff.


  • Harvard Campus

Once we dropped our bags at the hotel, we headed over to the train station and rode north to the Harvard Campus.  Walking among the old brick buildings and the historic campus quads was a bit surreal.  So many brilliant people have studied on that campus, including Mark Zuckerberg, President Obama, and even Louis Litt! 🙂  While we were there, it began to rain, so we ducked into the law library for cover.  When the rain stopped, the whole area was covered in an odd orange light, which created some really cool pictures.

Tip – On a chilly night in Cambridge, be sure to stop in at L.A. Burdick for some incredible hot chocolate!

    • St. Patty’s Day Party – Undisclosed Location

As we returned to the city from Cambridge, Jay’s friend invited us to a St. Patty’s day party at a private club.  We had to see how the good people of Boston celebrated Ireland’s high holiday, so we checked it out.  They had all sorts of green accessories, green party punch, and of course, Irish Car Bombs.  It was a blast!

  • Breakfast – The Thinking Cup

In the morning, I badly needed a good cup of coffee to shake off the lingering effects from the previous night’s festivities.  Fortunately, Yelp directed us to The Thinking Cup.  I ordered a Kenyan single origin pour over (coffee snob alert), and Brooke got a flavored latte.  We downed our delicious coffees and shared a breakfast croissant.  Hangover cured, onward to Freedom!


  • The Freedom Trail

The Freedom Trail is one of Boston’s most well-known tourist attractions.  It is marked by a 2.5 mile red-brick line leading to nationally significant historic sites.  Preserved and dedicated by the citizens of Boston in 1951, the Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.

A few tour companies offer guided tours of the Freedom Trail, but we opted to go self-guided.  We downloaded and used the Freedom Trail Walking Tour app (free), which included a map of the trail and a detailed description of all 17 historic places along the way.  Wear comfortable walking shoes if you plan to do the whole trail!  These are some of our favorite pictures from the day.

  • Lunch & Snacks – Carmelinas & Mike’s Pastry

After walking about half of the Freedom Trail, we decided to carb-o-load for some extra energy.  Mel is a devout pasta enthusiast, so she scouted out one of Boston’s premier Italian cafes, Carmelinas.  She and Jay opted for the slightly spicy Crazy Alfredo, and Brooke and I shared the Gnocchi al Forno.  Both dishes were fantastic!


For dessert, we walked across the street to the famous Mike’s Pastry to try their trademark cannoli.  The place was packed, and they only accept cash, but it was well worth the effort to get a delicious pastry.

  • Dinner – Luke’s Lobster

We finished the Freedom Trail and walked back to the hotel to kick up our sore feet.  After a bit of rest, and some wine, we walked over to Luke’s Lobster (pronounced lob-STAH) for dinner.  I recommend the clam chow-DAH and a sampler of three small sandwiches, shrimp, crab, and lob-STAH.


  • Boston Public Library

Our original plan for Sunday was to watch the big St Patty’s Day parade.  However, we woke up to an email from Aer Lingus, stating that they had cancelled our flight to Ireland that evening (more on that in another post).  We spent most of the morning scrambling to re-book our flight and rental car, and to adjust our itinerary.  Instead of trying to catch the end of the parade, we strolled across the street to visit the Boston Public Library.


The library is a beautiful old building with some nice artwork and magnificent architecture.  We explored most of the complex, including the courtyard, reading rooms, and map wing.

  • Harpoon Brewing

Our final stop in Boston, before heading to the airport, was Harpoon Brewing.  This brewery is located relatively close to the airport, so it was not far out of our way.  We grabbed two sampler flights and a large pretzel while we waited to take the brewery tour.  They offer a flight of experimental beers, which are available only at the brewery and included a Bacon Lager, a Peppermint Wheat Ale, and an Ancho Chile Porter!

The brewery tour was fun, and it included a stop in their second tasting room.  We had 15 minutes to try as many samples as we liked.  Definitely check out Harpoon when you visit Boston!

 Total Trip Cost Breakdown

The following table breaks down our transportation and lodging costs.  As you see, we spent very little actual money on these items, which allowed us to use our money for good times and great food in the city!

Item Points/Miles/Loophole Actual Cost
Airfare x 2 from MCI to BOS 11,342 Southwest RR Miles (used Companion Pass) $11.20
Westin Copley Place – 2 nights 24,000 SPG points $0
Boston Metro Train – 4 rides/ea $2.65 per ride x 8 $21.20
Uber from Brewery to Airport Friend Referral Credit $0
TOTAL $32.40

We really enjoyed our time in  Boston – partying like the Irish, learning about American history, and sipping some quality craft beers.  The city is an interesting blend of historic buildings and modern skyscrapers, and I definitely recommend a visit!


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