Food, Freedom, and Brews 3-DayTrip in Boston, MA
Day 1
Drop off your bags at your hotel of choice and begin your Boston weekend by heading over to the Boston Seaport Area for a brief Brewery Tour and lunch,
Where to Stay
Boston Seaport
Stop at Legal Sea Foods-Harborside to enjoy a nice meal on the water before checking out 3 local Boston Breweries in the Boston Seaport area
Breweries
After lunch begin your Brewery Bar Crawl of the Boston Seaport area. I recommend walking all the way down to Harpoon and then making your way back towards the Downtown area.
Dinner Recommendations
After Dinner head over to the area around TD Garden for some local Bar hopping or turn in early for some extra rest.
Additional Recommendation based on show times:
Day 2
Breakfast RecommendationÂ
Stop in at George Howell conveniently located next to The Godfrey before walking over to Boston Common to begin the Freedom Trail.
Freedom Trail
I prefer using the self-guided audio trail by Free Tours by Foot that can be purchased at the following link:Â
If you prefer a guided tour then you can book one of the tours offered by the official Freedom Trail site here:Â
According to their site, and my experience, the self led tour can take about 2 hours depending on your pace and how long you want to stay at each location. The trail is easy enough to follow by the markers laid out around the city, but if all else fails you can use one of the many Maps options on your cell phone if needed. I preferred starting in Boston Garden and ending at the USS Constitution Museum.Â
After the Freedom Trail, head on over to the North End to grab lunch at the Sail Loft
After Trail Pastries
Stop by one of, or all, Boston's famous pastry shops in the North End either after your Trail tour, or along the way to beat the crowds.
Spoiler: There is never a bad time to eat pastries.
New England Aquarium
Stop by the Aquarium after your lunch at the Sail Loft or when you can hardly move from eating so many pastries in so little time...
I highly recommend to buy the tickets ahead of time. The Aquarium is popular for school trips, families, and others enjoying a weekend in Boston.
Pre Dinner Drinks
Before heading back to your hotel to get ready for dinner, stop by the Sam Adams Downtown Taproom. I personally prefer this stop over heading out to the Brewery on a short trip when time is precious. The brewery is worth visiting if you plan on doing the full your experience. If not, save the trip out there and enjoy this Taproom nestled right in the heart of Boston
Night Time Options
Boston is a huge sports town. I highly recommend buying last minute tickets to a Celtics, Red Sox, or Bruins game, regardless if you have any other allegiances. The atmosphere will be electric and a fun way to spend your night. You can also look up concerts going on during your visit, if this wasn't already a main reason for your visit, to see if you can snag last minute tickets to a show.
If this is of interest, I recommend grabbing a quick bite to eat neat the sports venue or fully commit to the experience and get something at the game.
Dinner Options If Needed
Day 3
Breakfast Recommendation
Boston Public Garden
Walk to Boston Gardens after breakfast and enjoy the beautiful scenery. Sit on the same bench as Robin Williams and Matt Damon from Good Will Hunting.
Cambridge
Head over to MIT to take a walk around the campus. After, rent Citi Bikes and head over to Harvard Square and Harvard University to continue your academic tour.
Lunch Stop
Academic Break
Take an academic break and enjoy some good ole fashioned arcade games. Save some room at lunch for a grilled cheese as you embark on your high score quest.
Ice Cream Break
Before leaving Cambridge, continue your Dairy streak with a stop at a local favorite Ice Cream spot near Roxy's Arcade.
Boston Sunset Cruise
End your weekend with a romantic sunset cruise in the Harbor (weather permitting)
Trip Extension Recommendation
If you have more time, I recommend combining this trip with a visit to Newport. You can do them in any order you would like depending on where you are coming from. A free weekend guide of Newport is here:
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