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Boston, MA
Weekend Vacation Getaway

Destination Overview


Called the most European of American cities, Boston is an exciting contemporary city steeped in history, but keeping pace with the rush of modern times. History, culture, fine dining, shopping, sports and outdoor activities combine to make this a destination worthy of any special weekend. Sleek new architecture sits side by side with Colonial era history and distinct ethnic cultures remain loyal to their past and account for many of the unique neighborhoods.

Click picture to enlargeNorth ChurchBoston CommonSailing on the Charles

This is one of my favorite weekend destinations. Unlike some major cities, Boston is “manageable” and doesn’t overwhelm. It is easy to navigate and you can walk to most everything. It has pretty much anything a major city should have, but with a unique character all its own. It is just as much fun to just wander around as it is to have a planned itinerary. Charles Street offers art galleries, pubs and beautiful brownstones, Newberry Street is the place for great shopping, the Back Bay has great restaurants, the waterfront area has my favorite place for oysters and a cold one, the Public Garden is a beautiful urban oasis and you can enjoy the Charles River in any season.

The locals are passionate about their Boston sports teams (the curse is finally over!) and even if you are not a baseball fan, a day at Fenway is not something you will soon forget. Another passion? Believe it or not, ice cream, a topic many a Bostonian can wax philosophic upon, particularly in a pub. Best known for its Irish and Italian populations, Boston is also home to the 4th largest Asian community and a large African American population. Then, of course, there are the Boston Brahmins….what exactly do they look like?

As in many cities, the neighborhoods are distinct; Boston’s “Little Italy” in the North End, the Irish conclave in South End (also the waterfront district), Chinatown, the Back Bay, home to fashionable Newbury Street and the Beacon Hill areas and Cambridge across the River and the home of Harvard University are the most notable.

The many colleges and universities in and around Boston infuse the City with vibrancy and joie de vivre, making it a city for the young at heart. Patriot’s Day (Boston Marathon), opening day at Fenway, and St. Patrick’s Day are special events in the City and bring out old and young alike.

See Boston in pictures. Scrapbook.

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Click picture to enlargeSel de la TerrB&G OystersSonsie

Making Your Travel Plans

To make your travel plans you can go to our Weekend Planner for all the contact information.

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Getting There

Boston is accessible by air from anywhere in the country and the Boston airport is a short cab ride or water taxi into the City. New York to Boston is a 3 hour and 45 minute drive, 4 hours and 15 minutes from Philadelphia. It can also be reached from most major cities on the East Coast by Amtrak. New York to Boston on the Accela Express is about a 3 1/2 hour trip and Washington to Boston is about 6 1/2 hours.

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When To Go

Boston has plenty to offer for any season of the year. There is no bad time for a weekend visit, except perhaps with an impending snow storm in the dead of winter, but even then, the City is quite beautiful. The Boston Common and Boston Public Gardens are enjoyable throughout the year as is the Esplanade along the Charles River. In nicer weather you can boat on the Charles, enjoy outdoor concerts at the Hatch Shell, made famous by the legendary Boston Pops or while away a balmy day in one of the many pubs and restaurants with outdoor sidewalk seating. In the colder weather, you are greeted with a roaring fire in many pubs and restaurants, you can skate in the Commons and a walk through the Public Gardens after a snowfall can be quite magical.

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Getting Around

Boston is a fairly contained City with many activities within walking distance. Taxis are plentiful and the MTA is an excellent public transportation system. No car is needed and frankly, parking is an issue.

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There’s no longer any need to roll the dice on where you stay or to settle and stay at a “safe” national chain. BestWeekends Travel Advance Team takes the worry out of where to stay when you go away.

The BestWeekends Travel Advance Team does all the work for you. We research each destination by scouring the guidebooks, articles, blogs, reviews and rating systems. Then we visit the destination and stay in the properties. Finally, we talk to the locals to be sure we didn’t miss anything. The result: we post on our site only the best of what we experienced. You can book with confidence knowing that “we’ve been there” and that no one pays us for a review. Inside see our Featured Properties.

When you are away on vacation, there’s few things worse than a bad dining experience. We agree, so we follow the same process for identifying restaurants as we do for accommodations, but with an extra step. We believe that the best dining experience has the strongest combination of food, ambiance and service. Good food is a given in our recommendations, but the best food in the world just doesn’t taste as good in a poor setting and the best setting with poor service just doesn’t cut it for us. The BestWeekends Travel Advance Team only presents those restaurants that meet our strict criteria. Mangia….enjoy! Inside see our Recommended Restaurants.

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Things To Do

World class art and historical museums, wonderful jogging and walking routes, boating on the Charles River, ice skating in the Boston Commons, picnics in the Public Gardens, outdoor concerts at the Hatch Shell, sidewalk bistros, a wonderfully preserved “Little Italy”, Broadway road company theatre, Colonial era historical sites (remember Paul Revere?), upscale shopping and oh yes, the best baseball park in the country are just a sampling of what Boston offers. It has everything a major city should have, but with its own unique character and flavor. Somehow Boston just seems so much more manageable than other major cities. Best of all, most major attractions are within walking distance of each other. here's the complete list of Things To Do.

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BestWeekend' s Exclusives

After selecting our favorite places to stay and eat, we sat down and made a list of all the other things that would save you time and make your stay more enjoyable. The result is “Special Things” and “Good To Know, Good To Go,” BestWeekends Exclusives.

Special Things identifies unique, fun and romantic things for couples to do together in a particular destination. Good to Know is our list of the “best” of everything from breakfast to burgers, cocktails to after dinner fun and much, much more. Why stumble around trying to find the “best”….we’ve already done it for you!

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Don't Miss

  • A Sox game at Fenway
  • Boston Public Gardens
  • A stroll through Beacon Hill
  • Isabella Stewart Gardner Museum
  • Oysters, chowder and cold beer at the Union Oyster House
  • Boston Duck Tour
  • The Boston Pops at the Hatch Shell. May-July.

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News and Resources

Smart Destinations- Discounted Sightseeing Passes. Save up to 55%.
Boston Daily-Beantown Blog
Boston Magazine. All the "best of Boston" Winners
My Secret Boston. Uncovering the Secrets of the City.
The Boston Globe. The hometown newspaper.

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