Boston Uncovered: History, Culture & Food with a Local’s Touch

For your first day in Boston, start by grabbing coffee and a pastry or a light lunch at Tatte (pronounced like latte).

Afterward, head over to the Boston Tea Party Ships & Museum. This interactive museum brings the 1773 event to life with live actors, multimedia exhibits and a chance to throw tea into the harbor, recreating the historic protest that led to the American Revolution.

Next, choose between visiting the Institute of Contemporary Art or the Boston Children's Museum. At the ICA, explore modern and contemporary art exhibitions with a stunning view of Boston Harbor. The museum is known for its cutting-edge displays and rotating exhibitions. The Boston’s Children’s Museum offers hands-on exhibits that are engaging for children and adults alike. It’s a great option if you want to take a more playful and creative break after visiting the Tea Party Museum.

Then, take some time to relax and explore, enjoying the waterfront views, browsing the shops and embracing the modern atmosphere of Seaport. Finally, end your day with dinner at either Committee, which offers Mediterranean tapas in a lively setting, or Row 34, a popular seafood spot known for its oysters and lobster rolls.

For your second day in Boston, start with breakfast at the Boston Public Market, where you can enjoy fresh, local pastries and artisanal products from the region.

Afterward, head to the New England Aquarium to explore its fascinating marine life exhibits, including the popular penguin and sea turtle habitats, and take in the breathtaking views of the waterfront.

From there, make your way to the Boston Common, where you'll join a Freedom Trail tour. The tour begins at the Common, Boston’s oldest public park, and takes you through the heart of the city’s revolutionary past. You’ll visit landmarks like the Massachusetts State House, the Old State House and Paul Revere’s House, as a knowledgeable guide leads you through Boston's colonial history.

Before your tour starts, take a moment to enjoy the lively atmosphere of the Common and perhaps get a portrait from Nick Shea, known on TikTok as the “$1 portrait guy.” Nick spends his free time on a long green bench in the park, offering quick sketches for just $1. He’ll ask you your name, where you're from and what your plans are for the day while he captures your likeness on cardstock. Locals and tourists alike line up, sometimes waiting up to three hours for a portrait.

After the tour, meander through the North End, Boston's historic Italian neighborhood. It feels like a living museum, with small, family-owned shops, markets and cafes where the old-world charm still exists. Despite being a popular destination for tourists, it retains a strong sense of local character. You'll often see people conversing in Italian on the streets or hear lively chatter spilling out from the outdoor patios, especially during summer evenings.

Treat yourself to a cannoli crawl in the North End, tasting the differences and debating which one reigns supreme. Mike’s Pastry is known for its huge, classic cannoli with crispy shells and rich ricotta filling, often drawing long lines. Modern Pastry offers a more refined, homemade-style cannoli with a delicate ricotta filling and thinner, crispier shells and subtle flavors. Bova’s Bakery is open 24/7 and beloved by locals for its consistently good cannoli with a variety of fillings, including chocolate mousse and cream.

In the evening, enjoy some lighthearted entertainment at Improv Asylum, a comedy venue known for its sharp, witty performances. For dinner, the options are plentiful. Enjoy creative dishes at Table, savor a classic slice of Boston pizza at Regina Pizzeria, indulge in upscale comfort food at The Red Fox or have a cozy, home-style Italian meal at Mamma Maria. If you’re craving seafood, Carmelina’s offers delicious Italian seafood dishes, and Neptune Oyster is perfect for some of the freshest oysters in town.

Start your day with a delicious brunch at Contessa, where you can enjoy stunning views of the city alongside a sophisticated menu that blends Italian and American classics.

After brunch, head to Newbury Street for local boutiques mixed with luxury shopping in beautiful buildings. Take a slight detour to Copley Square to see Trinity Church and the Boston Public Library. Trinity Church is a Romanesque architectural masterpiece by H. H. Richardson, completed in 1877. As you stand in front of this grand structure, take a moment to reflect on the building's impressive foundation: it's built on 4,502 pilings driven into the once-muddy Back Bay. The church is widely regarded as one of the finest examples of church architecture in the country.

Next, take some time to explore the Boston Public Library, a Renaissance Revival masterpiece by architect Charles Follen McKim. Completed in 1895, the library reflects the grand influence of the Bibliothèque Nationale in Paris. Don’t miss the chance to admire its magnificent architecture, from the detailed doors designed by Daniel Chester French to the impressive interior halls to the Bates Reading Room with its famous green lamps.

Before you leave Copley Square, snap a picture with the Tortoise & Hare sculpture, a public art piece designed to commemorate the finish line of the Boston Marathon. This sculpture, unveiled in 1996 for the race’s 100th anniversary, marks the end of one of the world's most celebrated marathons. If you’re in town for Marathon Monday, you’re in for a treat. Colleges in Boston cancel classes for the day, and the city comes alive, flooding streets to cheer on runners in a party atmosphere.

Head back to finish up shopping along Newbury Street and then walk a block over to head up Commonwealth Avenue, a scenic, tree-lined boulevard in Boston’s Back Bay, known for its historic brownstones and beautiful parks ending at Boston Public Garden. Before the Back Bay was filled in, the Charles River flowed up to Charles Street, which separates the Public Garden from Boston Common. On the night of April 18, 1775, British troops used this area to board boats on their way to Lexington and Concord. While at the garden, don’t miss the famous Make Way for Ducklings statue, where you can take a fun photo with the baby ducks following their mother. You can also ride the beloved Swan Boats (in the summer) or ice skate (in the winter).

From the garden, cross the lagoon using the tiny suspension bridge — reputed to be the smallest in the world — and head toward the George Washington statue, which was unveiled in 1875 as Boston's first equestrian statue. Standing at 38 feet tall, it’s an impressive tribute to Washington, who was an outstanding horseman.

Next, explore the picturesque Beacon Hill neighborhood, just a short walk away. Start by visiting Sunflower House and the Charles Street Meeting House, both offering glimpses into the area's historical and architectural charm. Then, wander along Charles Street, home to quaint shops and Beacon Hill Books & Café, a beautiful independent bookstore where you can relax with a cup of coffee.

Don’t miss the Nichols House Museum on Mount Vernon Street, and stroll through Louisburg Square. To get the most iconic Boston tourist picture, follow Mount Vernon Street down to West Cedar Street. Take a left onto Mount Vernon Street. As you travel down Mount Vernon Street, notice the beautiful window boxes, and you will be at Boston’s most photographed street, Acorn Street. The view from the bottom looking up is the best view. The street is made up of river stones from the Charles River and is a wonderful street for posing for the perfect photo.

After a day filled with shopping, walking and picture-taking, enjoy a relaxing sunset. Pick up a customized charcuterie box from Kured and enjoy a picnic on the Esplanade, a scenic park along the Charles River. While there, stop by the Arthur Fiedler Statue, installed in 1985, which features a striking depiction of the legendary conductor of the Boston Pops. Nearby is the Hatch Shell, an amphitheater where the Boston Pops perform free concerts every July, adding to the lively, cultural atmosphere of the area.

Start your day with a delicious breakfast at Pavement, where you can enjoy freshly brewed coffee and a variety of pastries in a cozy, modern atmosphere. After breakfast, head to the Museum of Fine Arts (MFA), one of the most renowned art museums in the country. The MFA is home to an impressive collection spanning from ancient Egyptian artifacts to contemporary works, with special exhibits that cater to a variety of interests.

Next, visit the Isabella Stewart Gardner Museum, a unique and stunning museum housed in a Venetian-style palazzo. Founded by the eccentric philanthropist Isabella Stewart Gardner, the museum opened in 1903 and features her personal collection of art, which includes works by artists like Rembrandt, Vermeer and Titian. One of the museum's most intriguing aspects is the infamous art heist of 1990, when 13 pieces, including works by Vermeer and Rembrandt, were stolen and have never been recovered. This unsolved crime remains one of the greatest art thefts in history. The museum is also known for its beautiful courtyard, which is enclosed in glass and filled with lush greenery, fountains and sculptures, creating a peaceful, enchanting space to explore. If you’re lucky, you’ll be given the gift of song, like I was on a visit. I was serenaded in the middle of the atrium for everyone to see.

From the museum, take a short stroll to the Kelleher Rose Garden, located in the Back Bay Fens. This tranquil garden is part of the Emerald Necklace park system, offering a peaceful escape with over 1,500 rose bushes in bloom during the warmer months. It's a beautiful spot to relax and enjoy the beauty of the flowers.

Next, head to Fenway Park, home to the iconic Boston Red Sox. Fenway, one of the oldest ballparks in Major League Baseball, has been hosting games since 1912 and is a must-see for sports fans. If you're lucky, you can catch a Red Sox game, but if not, a Fenway Park tour offers an in-depth look at the park’s storied history, from the famous Green Monster to the classic hand-operated scoreboard. The park’s atmosphere is electric, with a deep connection to Boston's culture and history. The Red Sox, one of the oldest and most successful teams in Major League Baseball, have won multiple World Series titles, and Fenway Park is an iconic symbol of the city's passion for baseball.

For dinner, hit up Sweet Cheeks or Eastern Standard. Tiffani Faison was a runner-up on season one of Top Chef and went on to win Food Network’s Tournament of Champions, and her Fenway barbecue spot, Sweet Cheeks Q, is a homey restaurant serving up tender smoked meats like short ribs and pulled chicken, paired with sides like creamy mac 'n' cheese and barbecue ranch beans. Eastern Standard, a beloved Boston institution, reopened in late 2023 in a new location near its original spot, bringing back its iconic menu of duck confit, seafood platters and craft cocktails. Both are top dining destinations for both locals and visitors.

On your final day, start with brunch at Alden & Harlow, a cozy spot known for its inventive American fare and stylish ambiance in Cambridge.

Afterward, explore Harvard Square, home to the new Lovestruck Books, a romance-focused bookstore with a café and wine bar, and a hub for book lovers. In addition to shopping at Harvard Square’s unique boutiques, you can take a Hahvahd Tour, a fun and informative walk through one of the most historic areas of Cambridge, learning about the history and architecture of Harvard University.

Next, enjoy a food tour from Bites of Boston, where you'll embark on a guided walking tour of the South End neighborhood, sampling bites from local eateries like The Elephant Walk, Flour Bakery, Formaggio Kitchen, Burro Bar, anoush’ella, Bootleg Special and FoMu. This three-hour tour covers less than 1.5 miles and offers a chance to experience a mix of Cambodian-French fusion, Mexican, Eastern Mediterranean and Southern-inspired comfort foods, all while learning about the neighborhood’s history and architecture. It’s the perfect way to end your time in Boston.