The North End

It’s only fitting to begin in Boston’s oldest neighborhood. Locals began settling here in the 1630’s, with the term “Little Italy” following about two hundred and fifty years later. Today, this ⅓-square-mile neighborhood holds over 100 restaurants and a variety of attractions and shopping opportunities.

• Faneuil Hall, also known as Quincy Marketplace, this indoor/outdoor market offers plenty of places to eat, drink and socialize.
• The Old North Church, the signal lanterns that spurred Paul Revere’s Ride were hung from the steeple of this symbol of the American Revolution.
• The Paul Revere House, see where the silversmith whose midnight ride kicked off the American Revolution lived.
• New England Aquarium, explore the mysteries of the deep at one of the world’s premier aquariums.
• Shake the Tree, browse for funky finds in the North End’s newest eclectic boutique.
• Twilight, all in all, a simply fabulous boutique, with the perfect dress for any occasion.
• Bobbles and Lace, hunt for clothes, shoes, bags and jewelry in a myriad of styles.

Beacon Hill

Tucked between Boston Common and the Charles River, this charming cobble-stoned neighborhood is known for its Federal-style rowhouses, gas-lamp-lined streets and quaint shops.

• Massachusetts State House, Built in 1798, the golden-domed State House overlooks Boston Common from atop Beacon Hill.
• Charles Street, Beacon Hill’s main thoroughfare is teeming with wonderful restaurants, cafés, delis, boutiques and antique shops.
• Black Ink, find everything from Japanese trinkets to TinTin comic books in this shop full of “unexpected necessities.”
• Wish, this women’s boutique is filled with everything today’s elegant-but-trendy shopper could wish for.
• Paramount, a favorite of Beacon Hill locals, Paramount serves the best breakfast & brunch in Boston.

Back Bay

Boston’s signature skyscrapers – the Prudential Center and the John Hancock Tower – spring from the Back Bay. Lined with monied Victorian brownstones and exclusive shops and galleries along Newberry Street, the Back Bay is where the term “Boston Blueblood” was first coined.

• Boston Duck Tours, board your "Duck," a World War II amphibious landing vehicle renovated for Charles River sightseeing tours.
• Prudential Center Skywalk, ascend to the Prudential Center’s 50th floor for 360 degree views of Boston and beyond.
• Boston Common, ride a Swan Boat across the waters of the Boston Public Garden or enjoy a picnic in this 50-acre urban expanse.
• Copley Place & The Shops at the Prudential Center, find everything you need in the heart of Boston, with nearly two hundred fashionable shops and upscale restaurants.
• Newbury & Boylston Streets, browse Boston’s twin boulevards of bling, teeming with historic brownstones containing both high-end boutiques and less expensive bohemian-style shops.

Kenmore Square

Saying that Kenmore Square is only about Fenway Park would be selling it short. 81 days a year, Red Sox faithful turn the streets around Fenway into a sea of blue and red, but Kenmore also has a variety of colorful restaurants, museums and live music clubs crawling with folks who don’t know the difference between a balk and a batting donut.

• Fenway Park, home of the Boston Red Sox and the oldest park in baseball.
• Museum of Fine Arts, the MFA is one of the most comprehensive art museums in the world, with a collection of nearly 450,000 works of art.
• Isabella Stuart Gardner Museum, peruse this intimate collection of fine and decorative art housed in a 15th-century Venetian-style palace surrounding a lush outdoor courtyard.
• Hotel Commonwealth, visit the lobby’s diverse retail shops, including Persona Jewelry, The Wine Gallery, Hunts Photo shop and Panopticon Photography Gallery.
• Nuggets Record Store, pick through the extensive collection of CDs, DVDs and vintage vinyl.

South End

It’s unclear which came to this tranquil, leafy neighborhood first: the fabulous restaurants, boutiques and art galleries or the well-heeled professionals who frequent them. Either way, the South End continues to be Boston’s most thriving area.

• SoWa Open Market, a hip outdoor market with a variety of vendors hawking hand-crafted accessories, original art, indie designer duds and fresh breads, flowers and produce.
• Boston Center for the Arts, home to hundreds of artists and musicians, the BCA stages live performances and exhibitions throughout the year.
• The Galleries of Harrison Avenue, featuring major exhibitions and Friday Art Walks, SoWa’s 450 Harrison Avenue is home to 15 galleries and over 50 artist studios.
• Turtle, Turtle celebrates rising talent - emerging designers just coming out of their shells - from Boston’s South End to promising newcomers from New York, California, and even Argentina and Israel.