Destination: Boston

Steeped in Revolutionary War history, Kennedy-esque Brahmin accents, Harvard/Cambridge/MIT brainiacs, Cheers bonhomie and a sports fanaticism that borders on the Pentecostal, Boston combines New York highbrow and New England wildbrow into an earthy, working-class mélange all its own.

Whether it’s your first or umpteenth visit, this place just feels like home, though admittedly not your home.

Some of that is due to the city’s compact, tourist-friendly geography, with Logan International right there on Boston Harbor where it should be, just a short Mass Transit ride to Boston Commons and the start of the three-mile Freedom Trail.

Plenty of sightseers, especially families, spend their entire stay strolling, Italian hoagies in hand, to visit the trail’s 16 major historic sites, from the Old South Meeting House where the Boston Tea Party was born to the Old Granary Burying Ground where Samuel Adams, John Hancock and Paul Revere rest in peace.

Even if you’re not a history buff, Boston’s unique role as the midwife of America will captivate you as much as the sight of rowing sculls churning their way up and down the Charles River or the Green Monster, the 37-foot iconic left-field wall at Fenway Park.

If you’re headed to Boston, like as not you’re already pumped to see Beacon Hill, Faneuil Hall, Harvard Square and the Cheers bar.

Here are 10 lesser-known diversions to add to your must-see list:

Boston by gondola: Located just east of the Esplanade on the south shore of the Charles, Gondola di Venezia offers four gondola tour packages for two, with photos, roses, wine – and even a message in a bottle for those looking for memorable ways to pop the question.

Skinny House: Architecture (and tiny house) aficionados won’t want to miss the skinniest house in Boston, if not the entire country. This four-story rental, located at 44 Hull Street in the North End, measures just 10 feet wide by 30 feet deep. Perhaps it helps the city’s huge collegiate population better appreciate their dorm rooms.

Isabella Stewart Gardner Museum: Go for the paintings by Michelangelo, Rembrandt, Raphael and Botticelli; linger to enjoy the Venetian palace and gardens. Admission is free to visitors named Isabella, while those rocking Red Sox gear receive a $2 discount.

BostonMITcampusMIT campus: You don’t need a science degree to marvel at the 150-acre campus of the Massachusetts Institute of Technology, located on the north shore of the Charles in Cambridge. The campus is a living museum of impressive modern and postmodern works by the likes of Alvar Aalto, Eduardo Catalano, Frank Gehry, I. M. Pei and Eero Saarinen. Do see it.

Corey Hill Outlook: Located off of busy Washington Square in Brookline, this little-known park affords the city’s best views of its skyline from 260 feet, while its walking paths provide a welcome respite from the city din below.

The Museum of Bad Art (MOBA): Sure, you can see fine art anywhere in Boston. But if you long for a peek at artwork that’s so epically bad that it warrants – nay, demands! – its own museum, don’t miss MOBA. But be forewarned: you can’t unsee some of these disasterpieces!

Have a drink at Drink: Nestled in a former wool warehouse that overlooks Congress Street in the industrial neighborhood of Fort Point, Drink feels more like a cocktail party than a bar. Cheers!

Tango across the Charles: If by chance your visit to Boston should coincide with a full moon, the Boston Tango Society holds free tango lessons on the Weeks Footbridge beginning at 8 p.m.

Da Fenway: There is no better way to tap into the Boston experience than to attend a game or tour at historic Fenway Park, home of the Boston Red Sox. Built in 1912, the oldest ballpark in Major League Baseball still raises goose bumps, empty or full.

Escape the Room: Want to test your inner Spenser: For Hire, Boston’s iconic private eye? Escape the Room presents a seemingly ordinary space that’s actually a mystery puzzle. To win your freedom, you must find the hidden objects in the room, figure out the clues and solve the puzzle within 60 minutes. After which I would suggest a visit to Drink.

Photo credits: Shutterstock; photo of Fenway: Christopher Penler /; photo of MIT campus: Marcio Jose Bastos Silva /

Jay MacDonald

Jay MacDonald

Jay MacDonald is an award-winning journalist, author and blogger who incorporates humor and human interest into a broad range of topics. Follow him on Twitter @omnisaurus

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