Summer in the City: A 3-Day Boston Itinerary for Food, Fun & Culture

• First Pitch - Check-in: You have arrived in Boston and it’s time to drop your bags and hit the pavement! To best set yourself up to explore, I recommend choosing a hotel in Downtown or Back Bay for their central locations and walkability, making it easy to explore all the city has to offer on foot.

• Base Hit - Faneuil Hall & Quincy Market: The perfect way to kick off a weekend in Boston is visiting the famed Faneuil Hall & Quincy Market. History buff or not, you’ll appreciate good eats, shopping and all that took place in this historic landmark.

• Home Run - Dinner and dessert in the North End: A trip to Boston would be incomplete without dinner in the Historic North End, the city’s oldest residential neighborhood dating back to the 1600s and the ultimate place for authentic Italian food. I highly recommend Mare Oyster Bar, which is one of the few restaurants in the North End with a rooftop patio -the perfect place to sip on espresso martinis and indulge in fresh seafood and pasta. For dessert, treat yourself to a classic “Little Italy” dessert experience: a cannoli taste-off between two legendary bakeries, Mike's Pastry and Modern Pastry. Both institutions have been serving up delicious cannoli for decades, (Modern first, despite its name) each with its own loyal following. Other notable North End spots include Caffe Vittoria for post-dinner cappuccino and tiramisu, Bova’s for late-night food, and Pizzeria Regina for a slice of sausage pizza.

• If you’re interested in a tour, Cocktails and Cannoli has some incredible options to choose from and even offers customized tours!

• Rain delay - Visit a museum: The one that most likely comes first to mind is the Museum of Fine Arts (MFA), which is one of the largest art museums in the world, but a lesser-known treasure trove is the Isabella Stewart Gardner Museum where you can see for yourself the empty frames from the historic art heist in 1990. If you’re traveling with kiddos, you may want to consider the Museum of Science or the Boston Children’s Museum, both known for interactive and educational hands-on exhibits fun for the whole family (trust me).

Ask me how you can make your visit private!

• On Deck - Morning coffee and stroll: Grab a coffee (iced if you want to be like the locals) from Thinking Cup or Tatte and take in the beauty of Boston in the summer with a leisurely walk.

Boston has an abundance of parks, greenspace and architecture so you’ve no shortage of options, but here are a few of my favorites:

• Beacon Hill: One of Boston’s most picturesque neighborhoods! Be sure to check out Acorn St and Charles St.

• Esplanade: Exercise on land or in the water with a kayak or paddleboard on the Charles River.

• Boston Common and Public Garden: An absolute must while all the flowers are in bloom and the perfect opportunity to take a ride on the Swan Boats.

• Freedom Trail: A 2.5-mile walk covering 16 nationally significant sites that tell the story of the American Revolution.

If you need an accessible alternative to walking, consider a hop-on hop-off bus. If you prefer a more organized and instructive experience, consider a guided tour.

• Seventh Inning Stretch - Afternoon tea: With all that walking, you’ve worked up an appetite and afternoon tea at the iconic Raffles Boston feels like just the right reward. Situated on the 17th floor with views of Back Bay, Long Bar & Terrace offers choices of tea or tea cocktails paired with sandwiches, scones and cakes. Cheers!

• Out of the Park - Enjoy the sights from the sky: Who doesn’t love a good view? What better way to see Boston than from a helicopter? Helicopter Tour Boston has a variety of flight options from a romantic sunset tour to a more thrilling Doors Off tour and all tours can be made private. If you’re looking for something a little more low-key, the Skywalk Observatory at the Prudential offers unparalleled views of the city’s skyline, with visibility up to 100 miles on a clear day!

• Walk-Off - Dinner at Contessa: Keeping with the theme of views – Contessa is another restaurant with unmatched views of Back Bay at sunset. Located on the 17th floor of The Newbury overlooking the Public Garden, Contessa is meticulously designed and decorated and absolutely drenched in natural light! You can’t go wrong with anything off the Italian-inspired menu, but my favorites include the meatballs, squash carpaccio and the sweet corn ravioli. For dessert, treat yourself to olive oil gelato!

• Rain Delay: Head to the Mandarin Oriental or the Raffles for a spa day!

• Batter Up - Brunch at Lincoln Tavern: Located in “Southie,” this staple restaurant is known for its “bucket of bubbles” and fruity pebbles pancakes. The perfect cure after a late night out! Make a reservation or get there early.

• Double Play - Get out on the water: Boston is beautiful from within but seeing it from the water provides a whole new perspective. There are a multitude of options depending on the vibe you’re looking for, but Duck Boat is the quintessential Boston tour offering both land and water sightseeing. Pedal Boat is a fun way to get some exercise while taking in the sights (don’t worry, you don’t actually have to pedal for the boat to move) and a whale watch can be fun if you’re visiting during migration season!

• All-Stars - Get a taste of Boston: Since three days in Boston is not long enough to taste the entire city, head to Boston Public Market or Time Out Market for a sampling of the city’s best culinary fare.

• Grand Slam - Visit Fenway Park: If you are lucky enough to visit Boston when the Sox are playing, you have to go to a game. Even if you are not a sports fan, the energy at Fenway Park is enough to make anyone smile. Get as Fenway Frank and belt your heart out to Sweet Caroline. If the Sox aren’t playing, take a tour of the stadium and imagine yourself catching a fly ball.

• Rain delay: Go shopping on Newbury St.