Off the Beaten Path

By Wendy van Diver

THERE’S NO OTHER TOWN QUITE LIKE BOSTON, Massachusetts. Infused with colonial history, abundant in culture, and home to 50 colleges and universities, this charming seaport city offers plenty of sites and attractions to entertain visitors. You can hop on trolleys and duck boats, follow the footsteps of America’s founding fathers with a costumed guide, and take selfies in front of dozens of historic sites. But to really get a feel for this town, it’s worth stepping off the beaten path.

Boston Common in winter  | Kyle Klein / Greater Boston Convention & Visitors Bureau
Boston Common in winter | Kyle Klein / Greater Boston Convention & Visitors Bureau

I first visited Boston as a teenager when my older brother moved there in the 1970s. Together, we followed The Freedom Trail (a 2.5-mile walking tour that leads to 16 historically significant sites including museums, churches, meeting houses, cemeteries, and a ship) to tell the story of the American Revolution. On another visit, my brother chartered a fishing boat in Boston Harbor, and I cheered him on as he snared a tough-fighting bluefish. We ate at Local Seafoods when it was only a single restaurant, not a chain. And we took the MBTA Subway (commonly known as the “T”) and walked wherever we went. Forty-plus years have passed, and I have just returned from another trip to Boston. I’m happy to report, it’s as charming as ever.

Boston is a very walkable town, so plan to wear your comfiest boots or walking shoes wherever you go. Start by getting acclimated with a stroll through the narrow streets of Chinatown and pick out an appealing dim sum restaurant to return to during your trip. Or head to Boston Harbor and check out the options for a harbor cruise. Although most companies take a hiatus in the coldest winter months, a couple of heated luxury ships still have offerings.

Boston’ skyline view from the South Boston Waterfront (or Seaport) District | Boston Harbor Association
Boston’ skyline view from the South Boston Waterfront (or Seaport) District | Boston Harbor Association
Faneuil Hall | Greater Boston Convention & Visitors Bureau
Faneuil Hall | Greater Boston Convention & Visitors Bureau

The famed Freedom Trail, marked with a red line painted into the pavement, is one of Boston’s most popular tourist attractions. You can book an informative 90-minute walking tour with The Freedom Trail Foundation, or if this sounds too touristy, follow it on your own. Many of the historic sites along the trail have docents and plaques with in-depth information. In addition, I discovered The Norman B. Leventhal Walk to the Sea, which stretches about a mile, from the Massachusetts State House to the Waterfront Long Wharf. The Walk to the Sea features eight locations. Each point is marked by a pillar with a QR code providing information, or you can use your cell phone for a virtual tour.

Beyond historic buildings, Boston prides itself on its green spaces. Beyond the park that’s on every tourist’s list, Boston Common, check out the Rose Kennedy Greenway. Home to a splendid carousel with hand-carved characters inspired by sea creatures and more, this park is a relatively new part of the urban landscape. Next, pop into The Boston Public Market for coffee, or anything your heart desires.

Inside the John F. Kennedy Library and Museum | JFK Presidential Library
Inside the John F. Kennedy Library and Museum | JFK Presidential Library

On my most recent trip, I visited two places that were new to me. The John F. Kennedy Presidential Library and Museum, located on the campus of the University of Massachusetts Boston, is stunning. The museum overlooks the sea and the city of Boston—two of President Kennedy’s greatest loves. I have visited several presidential museums and was very impressed with the way the life, leadership, and legacy of President Kennedy was presented. I felt like I had taken a time capsule back to the early 1960s. Drop-in admission is available on a limited basis, so it is advisable to reserve your tickets online.

I also spent a couple of hours at the Isabella Stewart Gardner Museum. It’s mind-boggling how much one person can collect in a lifetime! In the late nineteenth century, Isabella Stewart Gardner, a modest art collector, inherited 1.75 million dollars upon her father’s death and, with her husband, bought land in the Back Bay Fens neighborhood to build a museum. Isabella spent the remainder of her life on a buying spree, acquiring an astounding number of objects from around the world to fill her four-story museum building—a fifteenth-century style Venetian palace. The Isabella Stewart Gardner Museum comprises more than 2,500 paintings, sculptures, furniture, textiles, silver, ceramics, rare books, and archival objects from ancient Rome, medieval Europe, Renaissance Italy, Asia, the Islamic world, nineteenth-century France, and America.

To round out your visit, be sure to check out the grounds of a college campus or two, order lobster ravioli at a tiny restaurant in the North End, find new fashions in the boutiques on Charles Street and Beacon Hill, and take the “T” from point A to point B. With 23 distinct neighborhoods, you’re bound to find something new around every red-brick corner.

Isabella Stewart Gardner Museum | LnP images / shutterstock.com
Isabella Stewart Gardner Museum | LnP images / shutterstock.com

Plan Your Trip

Nonstop and connecting flights from San Diego International Airport (SAN) to Boston Logan International Airport (BOS) are available daily. From the airport, you can take the MBTA (the “T”) Subway, app-taxi, or cab to your accommodations.

Choose a hotel in a central downtown location with easy access to The “T.” Two affordable options are Langham and Harborside Inn.