Skyline from Boston Harbor — Photo courtesy of Jessica PolizzottiBoston's place in American history gives this booming city a cozy feel that attracts visitors to return and locals to lay down roots. A mix of old and new structures meld together to form a landscape that intertwines history among skyscrapers to give you a taste of Boston's past while keeping your feet firmly planted in its present. Combine walks around the city with stops at some of the best stores, restaurants and nightspots to find a perfect balance of old and new for your first time in this dynamic city.
Freedom Trail — Photo courtesy of Greater Boston Convention & Visitors Bureau
History via the Freedom Trail
No trip to Boston would be complete without making a few stops along the Freedom Trail. Easy to do, as the red line of this trail acts as a map of the city connecting downtown all the way through Charlestown with historical sites nestled within the neighborhoods along the way. Pick and choose those you want to see while stopping to shop at Faneuil Hall Marketplace and eat at the restaurants that you'll encounter within easy reach of the trail.
History buffs will find the Colonial-type setting part of the allure of Union Oyster House. The oldest continually operating restaurant in America, which just happens to serve some delicious eats, has a menu filled with New England favorites.
For those looking to sample some Italian delights, you must make room for food in Boston's North End. Stop at old favorites like Giacomo's, where perfect plates of pasta are prepared each night, or dine at new spots like Quattro where you'll get a sampling of food from four popular Italian eateries.
Newbury Street — Photo courtesy of Greater Boston Convention & Visitors Bureau
Shop and People-Watch on Newbury Street
A stroll down Newbury Street will allow you to shop, people-watch and make a few stops to refuel along the way. When most think of Newbury, they think of high-end, high-priced shops lining this Back Bay street; those that the regular Joe or Jane would need a makeover just to enter. However, Newbury Street's stores are as diverse as the population of the city itself spanning from the highest of high-end, like haute couture giant Chanel to fashionable and even some affordable boutiques like No Rest for Bridget.
Stores are not the only reason to visit Newbury. A variety of restaurants and coffee shops make their home here too. Stop in for food or a drink at Met Back Bay or enjoy people-watching from there on a warm day. Some locals claim this is the perfect way to end the day.
Walk the HarborWalk
Boston's waterfront location has been embraced by developers who have transformed the Harbor into one of the city's must-see spots. Take in the breathtaking views from the walkway that meanders along the water's edge, connecting Boston's waterside neighborhoods with the downtown area. Here you'll find parks for picnics, art to view and vessels to board, as well as a constantly increasing number of hot new restaurants and bars to try.
Favorites include Liberty Wharf's collection of restaurants that offer not only excellent eats, but also amazing views. Enjoy a hearty meal paired perfectly with a great wine at Del Frisco's, or dive into a plate of New England seafood at Legal Harborside. Then make your way to Legal's third floor (rooftop) patio that's an open-air haven for the trendy set to drink the night away on a warm evening.