Boston: On the Ground

Insider Tour Boston: On the Ground

A vibrant hub of modern culture in the historic heart of the United States, Boston is a perfect mix of old and new. Explore the cobblestone streets of one of the first American cities with W Boston Insider Shila Wheeler, and experience the new age of foodie finds, great shopping and bustling bars like a local.


Boston Common


Established in 1632, Boston Common is the oldest city park in the country. During the warmer months, check out festivals, food vendors, theater performances and in the winter grab your a pair of ice skates for gliding on the Frog Pond ice rink.



Freedom Trail


Immerse yourself in the history of Boston with a tour of 16 iconic sites along a two-and-a-half mile path through the city. Join a tour led by a costumed expert or grab a map and guide yourself from Boston Common all the way to the Bunker Hill Monument.



Fenway Park

4 Yawkey Way


One of the most popular things to do in Boston during the warmer months is catch a game of the city’s beloved baseball team. Revel with the team’s fans and join in longtime traditions as they cheer on the eight-time world champion Boston Red Sox.


Wink & Nod

3 Appleton St


A secret spot on a tree-lined South End cobblestoned street, this speakeasy was inspired by Martin Lomansey’s iconic quote: “Never write if you can speak; Never speak if you can nod; Never nod if you can wink.” Come and do both, with an artisanal cocktail in hand.



348 Congress St


Renowned Chef Barbara Lynch breaks the mixology mold with her Fort Point establishment. There’s no printed beverage menu, as cocktail inspirations vary daily with local produce and libations. Ask about the secret Drink burger with housemade pickles and Thousand Island-inspired dressing.



The Beehive

541 Tremont St


Sip and shake at this South End bohemian hotspot for nightly live jazz. The Beehive’s atmosphere has a throwback feel to Moulin Rouge. There is no cover for nightly entertainment, and during summer months, the brick patio is the perfect spot to enjoy an al fresco cocktail.


80 Dartmouth St


True to its name, this South End accessories boutique features sculptural contemporary jewelry by Sophie Hughes. The intimate space also houses Sophie’s workshop, where she creates custom pieces on site, a great chance to see a craft in action.




60 Northern Ave


Nearly a hundred years old and having inhabited a historic Back Bay building for the latter part of the twentieth century, the venerated retailer recently moved to a stunning waterfront property several seasons ago. Since then, fashion lovers make the pilgrimage for Jonathan Simkhai’s designer collection and one-of-a-kind accessories found nowhere else in the city.



Daniela Corte

201 Newbury St


With a garden level storefront and an atelier upstairs, designer Daniela Corte is taking over more than just a Newbury brownstone. Fall in love with Corte’s impeccable separates and signature legging bar. Her Resort/Swim collection has been featured in the Sports Illustrated Swimsuit Edition for three years running!



Ball + Buck

144B Newbury St


Get ready for a revolution: Ball and Buck is a Newbury Street boutique known for great outdoors-inspired menswear. With an active barber shop located inside, this taxidermy-adorned space features rugged leather goods and hunting-quality apparel that somehow fit in on a city sidewalk.


Whisky Saigon

116 Boylston St


Bold and brand new, Whisky Saigon spins top 40 mash-ups. Located just a block away from W Boston, the large dance floor caters to packed crowds on Friday and Saturday nights.



The Sinclair

52 Church St, Cambridge


Hidden on a Harvard Square side street, The Sinclair is Boston’s newest live music venue. Listen to up-and-coming bands and solo artists in an industrial-chic atmosphere and grab a bite at gastropub kitchen, where food and music inspire each other.



Cafe 939

939 Boylston St


Berklee College of Music’s alumni have received 250+ Grammys, and Cafe 939 is one of the best spots to see up-and-coming acts before they go platinum. The all-ages, student-run music venue and coffee house showcases emerging student talent that’s just about to break.



W Boston


Dance until the late hours of the night at Tunnel, W Boston’s destination nightclub. The club’s custom LED light art installation spans the ceiling and is synchronized to the beats of the DJ booth. Guest DJs are featured every Tuesday, Thursday, Friday and Saturday.