10 Quintessential Boston Experiences

Jul 2014

With the summer travel season in full swing and the 4th of July around the corner, here are 10 quintessential Boston experiences you shouldn’t miss when you’re in town.

wingaersheek beach gloucester ma

Boston boasts some of the best beaches around, many within easy reach of the city.  Revere, Carson and Boston’s Harbor Islands have public transportation to get you there.  A trip to Castle Island combines a meal at the infamous Sullivan’s and a walk along the water and leaves you the afternoon for other attractions.  Singing Beach can be reached by the MBTA, and others within an hours drive {like Wingaersheek Beach in Gloucester above } are well worth the effort.  Just remember to get their early, as you’ll find many visitors also have sand and surf on their mind.

boston skyline charles riverBoston’s skyline at sunset is a beauty.  Make an effort to walk along Memorial Drive on the Charles River bike path. Running next to the banks of the Charles, this popular pathway winds along the north edge of the city proper.  There are great views from all vantage points and you’ll view the city in all it’s glory.

boston chowderWhile I think you’ll find the best New England clam chowdah right here in Boston, everyone has their favorite location to sip and slurp.  Do you like it thick enough to hold a spoon upright, or thinner with more broth, served in a bread bowl and loaded with clams and potatoes?  B & G Oysters, Ned Devines, Legal Seafood and Turner Fisheries are a few of the top contenders.  I’m going to recommend you make your own decision.  With many award winning varieties, it’s on just about every menu.  Try a bowl at least once during your visit and taste a northeast specialty.  PS-you might want to sneak in a lobster roll too!

old north church paul revereLove history? Then don’t miss at least part of the Freedom Trail.  Two and a half miles of 16 sites steeped in history make up Boston’s version of the Yellow Brick Road. This path of brown pavers starts at the Boston Common and will lead you on a winding outdoor museum tour ending at the U.S.S. Constitution.

japanese lantern public garden bostonGreen space in the city occupies every neighborhood you will visit.  One of my favorites is the Public Garden.  The Japanese lantern near the footbridge was a gift to the city in 1904.  Built in 1634, this space is America’s oldest park.  The Make Way for Ducklings sculpture will delight both young and old, especially in the early evening when the surrounding trees twinkle with fairy lights.  In any season, it’s a beautiful spot to stop and sit a spell.

fenway-parkFenway Park is seeping with sports history.  As the oldest and most iconic baseball park in the country, to experience a game here is to experience the essence of baseball.  The infamous Green Monster is a city treasure and with a hot dog in one hand and a beer in the other Take me Out to the Ball Game will never sound the same again.

bunker hill bostonFind out where the saying Don’t Shoot ‘Til You See the Whites of their Eyes originated.  A horrid thought indeed, but this is the spot where that famous cry rang out in 1775 at the Battle of Bunker Hill.  If you dare, climb the 294 stairs of local granite and you’ll be rewarded at the top of the obelisk with a spectacular view of the surrounding area.  After your heart has stopped pounding, {and believe me, it will pound} stroll down the hill and have a drink at the Warren Tavern, one of the cities oldest and most infamous Charlestown watering holes.

isabella stewart gardiner museum bostonBoston has many wonderful museums covering the gamut of artwork, but one of my favorites is the Isabella Stewart Gardner Museum.  Tucked away not far from the well known Museum of Fine Arts is the vibrant collection of a woman who knew her way around the globe.  Completed in 1903, the artwork celebrates the worldly travels of a lifetime of curating and collecting.  Set in an intimate, Moorish setting, the center courtyard is sure to knock your socks off.  The new Renzo Piano designed wing brings the museum into the 21st century and houses educational facilities and performance rooms.  Cafe G features a menu inspired by the flowers and music of the museum.  The cozy reading room provides a spot for finishing off your afternoon of traveling vicariously through Isabella Stewart’s collections and generosity.

charles-street shopping-bostonStarting at the northeast corner of the Public Garden and stretching to the end of Beacon Hill, Charles St. shopping offers a more boutiquey experience than its better known Newbury St. cousin.  The feel is very European, with a mix of small specialty shops, unique restaurants and yummy dessert cafes.  Make sure to venture off the main drag and you’ll find a bounty of one of a kind goodies you won’t find elsewhere.

DSC_0551Finally, to cool off in this summer heat, make your way to a summer spot that is enjoyed by kids of all ages.  The Rings Fountain’s 64 jet sprays seem to magically appear and shoot water to heights of thirty feet on a section of the Rose Kennedy Greenway.  The unpredictable jets release water ribbons into the sky and delight everyone on a beautiful summer day.

So…when are you coming to town?


  1. noel says:

    What an excellent guide of the cool and fun places to visit in Boston. I totally love the Isabella Gardner Museum – precious!

    • alison says:

      I could spend days in the Gardner-they also have a pretty amazing gift shop where the inventory changes to work with the current exhibit. It’s one place in Boston that transports me to another country every time I visit.

  2. A fabulous guide Alison, with superb photos. I am totally sold. I will be there as soon as possible 🙂 There’s so much to love about this city in your guide …what a cool idea the water jets are.

    • alison says:

      Jackie-I hope you’ll let me give you some personal tips when you do come. {i know I’ll certainly ask the same of you when I visit Spain!}

  3. Great guide here Alison on Boston! We were there just a few weeks ago and even though we only spent less than a day there, we were able to see quite a bit and explore the beautiful city.

    One other experience I would add that we really enjoyed was the famous ‘Cheers’ restaurant which was really cool! Close to the Boston Common I would recommend anyone to head there for a bite to eat before heading on the Freedom Trail to learn about Boston’s rich history.

  4. Thank you for this post … I would love to visit. I didn’t know that Boston had so many green spaces … that’s excellent! I adore museums so they’d definitely be on my list.

  5. Lots of great tips for what to see and do when we visit Boston! The 2-1/2 mile Freedom Trail looks like a must do :-).

  6. What a wonderful collection of attractions. The Freedom Trail sounds fascinating and I HAVE to try clam chowder sometime soon!

    Having no interest in sports, the only thing I had my doubts about was the baseball game, but you’ve persuaded me that I would enjoy that too (I think it was the hot dog and a beer that swung it!)

  7. Tim says:

    Love the photo of the street lamp…very cool.