Best Things To Do In Boston for The Sophisticated Woman

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Our list of the best things to do in Boston offers a myriad of experiences for those with discerning taste. Are you a lover of art, culture, and history? But you also enjoy fine dining and upscale shopping? Well, it’s all here. Be sure to also check out our article on the best places to stay in Boston.

Boston is a city with all the best a larger city offers, with a smaller town ambience. And you’ll love how easy it is to get around. Not only does it have an excellent transportation system, but it is a very walkable city. So come along with as us as we explore the best things to do in Boston!

Art and Culture:

Museum of Fine Arts (MFA): Begin your journey into the artistic heart of Boston at the Museum of Fine Arts. Home to an extensive collection of masterpieces, it spans the gamut from ancient civilizations to contemporary art. If you’re an art enthusiast the MFA, you can certainly enjoy a few enriching hours here.

Isabella Stewart Gardner Museum: A true gem in the city, the Isabella Stewart Gardner Museum is not only an architectural marvel but also a repository of incredible art. Wander through the lush courtyard and explore the carefully curated collection that reflects the eclectic taste of its founder.

Boston Symphony Orchestra: Elevate your cultural experience by attending a performance at the renowned Boston Symphony Orchestra. The Symphony Hall, with its stunning acoustics, provides the perfect setting to indulge in classical music, showcasing the city’s commitment to the arts.

Enchanting Experiences

Walking Tour of the Freedom Trail: Immerse yourself in the rich history of Boston with a guided walking tour along the iconic Freedom Trail. As you traverse the cobblestone streets, you’ll encounter historic sites, including the Massachusetts State House and Paul Revere’s House, providing a captivating glimpse into the city’s revolutionary past.

Sunset Cruise: Unwind in style with a sunset cruise along Boston Harbor. Step aboard a luxurious yacht and watch as the city’s skyline transforms under the warm hues of the setting sun. With a glass of champagne in hand, this enchanting cruise offers a unique perspective of Boston, combining elegance with breathtaking views.

      Fine Dining

      Oleana: For a culinary journey that mirrors the sophistication of the city, Oleana in Cambridge is a must-visit. Offering a Mediterranean-inspired menu crafted with locally sourced ingredients, this restaurant has earned its place among the best in Boston.

      Menton: Indulge your palate at Menton, a French-Italian gem in the Fort Point Channel neighborhood. Helmed by Chef Barbara Lynch, the restaurant combines exquisite flavors with impeccable service, creating a dining experience that is both refined and memorable.

      No. 9 Park: Nestled in an elegant townhouse overlooking Boston Common, No. 9 Park is a beacon of culinary excellence. Under the guidance of Chef Barbara Lynch, this restaurant seamlessly blends modern techniques with classic flavors, providing a gastronomic journey for the sophisticated palate.

        Upscale Shopping

        Newbury Street: Prepare for a shopping spree along the upscale Newbury Street, where designer boutiques and high-end retailers line the picturesque brownstones. From luxury fashion to exquisite jewelry, this iconic shopping destination caters to the refined taste of the sophisticated woman.

        Copley Place: A shopping oasis in the heart of the city, Copley Place offers a premium selection of designer brands and upscale retailers. Immerse yourself in a world of luxury as you explore this stylish destination, providing a perfect blend of shopping and entertainment.

        Prudential Center: Elevate your shopping experience at the Prudential Center, where a mix of high-end stores and boutique shops awaits. With its central location and diverse offerings, this destination caters to the discerning shopper seeking the best in fashion, beauty, and lifestyle.


          Enjoy your stay in Boston! Whether you opt for a visit to the iconic Museum of Fine Arts, a historical walking tour or an enchanting Sunset Cruise, you’re sure to have a memorable trip!

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          Susan Cooper

          I'm a "woman of a certain age" who loves to travel, preferably in style! There's something exciting about exploring new places, meeting fellow travelers, and experiencing local cuisine. But I also really enjoy relaxing at a cafe. And it's always fun to absorb a little culture and history along the way!

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