Boston with Teens: A Perfect Family Day

Boston with Teens: A Family Vacation


Boston promises a rich blend of historic landmarks, impressive architecture and, in more recent years, great food – it's an excellent destination for a vacation with teens. This perfect day of family activities in Boston with teens is sure to be a hit!


Charlie's Sandwich Shoppe, at 429 Columbus Avenue (617-536-7669?) in Boston's South End, is a living, time capsule, an old-school diner frozen in time. Nothing appears to have changed since it opened in 1927 when this was a working-class neighborhood and the shop was open 24 hours a day, 7 days a week. When, in 1959, the decision was made to close on Sundays, they realized they had never even made a key.

In a city steeped in history, Charlie's offers an excellent start to the day, just as it has for generations of politicians, celebrities, electricians, plumbers and their families. Grab a few of their coveted seats, but don't expect to order a latte here. This is a real-deal diner, without any pretension. The menu is varied and reasonably priced, and the portions are large, so start your Boston family vacation with some blueberry pancakes, waffles and eggs made just right!

Most of Boston's South End was constructed in the mid-nineteenth century, and it is a marvel of aesthetically uniform rows of five-story, red-brick bow fronts in various architectural styles. A brief stroll through this neighborhood provides a real appreciation for history and economic issues. Though it began as a wealthy neighborhood, by the middle of the twentieth century, the South End quickly deteriorated as the elegant homes were broken up into tenement apartments for the rapidly expanding immigrant population. The South End dodged a fatal bullet in the 1960s, when city planners were met with fierce opposition after they had begun razing acres of housing to construct a highway into the city. The project was abandoned, but not before leaving an urban scar that remained for several years. Local residents responded by establishing community gardens on the cleared land, and City planners then relocated the Elevated Washington Street line of the subway and placed it underground where the highway project had been withdrawn.

By 1990, the Southwest Corridor Park was completed, creating a 4.7-mile stretch of tennis courts, playgrounds, basketball courts, and walking, jogging and biking trails – a treasure trove of fun Boston activities for teens. A stroll through the South End and the Southwest Corridor Park provides a testimony to the power of a community's desire to preserve the past and restore it for present and future use, and it is a perfect morning activity for a family vacation in Boston.

Take the "T" from Prudential inbound to Haymarket. Exit at Haymarket, and if you've planned your visit on a Friday or Saturday, you and your family can experience the excitement and commotion of the open-air fruit and vegetable market, held here since 1830. But whatever you do, don't touch! Stop by the Rose Fitzgerald Kennedy Greenway Conservancy, a mile-long stretch of gardens and parks, and take in one of the numerous festivals, performances or kid's activities held at this Boston green space.


At the southern extremity of the area is Urban Adventours, offering bike tours of Boston from their location at 103 Atlantic Avenue on Boston's scenic Waterfront. Their knowledgeable staff combines a passion for cycling with a love and respect for Boston, its architecture and history. It's an excellent way to get some exercise and see the sights of Boston with teens. Tours depart at 10AM, 2PM and 6PM, including rides to the Emerald Necklace, Boston Harbor or even Fenway Park to catch a game or tour the hallowed grounds. They also offer private, customized or extended rides, following the trail of Paul Revere or even a one or two-day trip to Provincetown on Cape Cod. Call for reservations at 800-979-3370.

Another excellent activity in Boston that teens might find interesting is the Faneuil (pronounced like "flannel," but without the "L") Hall Marketplace (Address: 4 South Market Street, Boston, MA). Here, an abundance of talented performers populate the cobblestone plaza, which is flanked by restaurants and old, majestic trees. Also nearby, at 340 Faneuil Hall Market Place, is Durgin Park (617-227-2038), a historic dining establishment where a surly wait staff serves up a healthy (and humorous) side of attitude – a sure bet for entertaining teens. In Boston, Durgin Park is an icon, and while it can be pricey, the portions are huge and the food to die for. Try the prime rib or the clam chowder.

Teens in Boston will find Heaven in the Back Bay area along trendy Newbury Street, which offers a unique and eclectic mix of independent shops, salons and high-end fashion boutiques. Designed for foot traffic, the street features broad, red-brick sidewalks and storefronts that extend into the sidewalk. You can find nearly anything here, with hundreds of retail options along an eight-block stretch. If you've made it as far as Hereford, wedge yourself into Emack and Bolio's Ice Cream (290 Newbury Street Boston, MA 02215; 617-536-7127), which offers more than 100 flavors throughout the year. You'll have no trouble finding it - the crowd of patrons is a dead giveaway, and there is no better way to please the family while traveling in Boston.


What better place to wind down your family day in Boston than Hanover Street in the North End? The North End is Boston's Little Italy, and Hanover Street offers dozens of Italian restaurants, pizzerias and cafes covering every budget and cuisine. The Daily Catch at 323 Hanover Street (617-523-8567) is a top choice for simple, inexpensive pasta, and it's conveniently located across the street from Mike's Pastry at 300 Hanover Street (617-742-3050). With unbeatable cannoli and excellent Italian dining so close together, where else do you need to look?

It has been said that if you don't like the weather in Boston, wait a moment and it will change. At some time during the course of your family vacation in Boston, you will probably catch a glimpse of one of the city's most treasured landmarks atop the "old" John Hancock Building. Since 1950, a weather beacon has been forecasting the weather, using predictions from a meteorological company on the 26th floor. An intellectual undoubtedly came up with the following poem to decipher the signal:

"Steady blue, clear view
Flashing blue, clouds due
Steady red, rain ahead
Flashing red, snow instead"

No matter what the weather may be (it could truly be anything!), there is no shortage of options for a perfect day in Boston with teens.

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