Boston is one of my favorite cities in the world, a blend of big-city excitement with the charm of a quieter, cleaner, and safer environment. Around every corner, there’s something new and surprising—whether it’s a 300-year-old building or a trendy new restaurant. The city exudes a youthful, vibrant energy, yet is steeped in American history. It’s also a fantastic destination for families, offering countless activities to keep kids entertained.
Where to Stay: Boston boasts a wide range of hotels to choose from. I’ve stayed at several, including the Boston Harbor, The Langham, Marriott Long Wharf, The Bostonian, and Marriott Copley Plaza. My favorites are centrally located, providing easy access to the city’s main attractions. The Langham offers a short walk to most sites, while the Boston Harbor and Marriott Long Wharf provide stunning views of the harbor. Marriott Copley Plaza is perfect for those who want to be near shopping hotspots like the nearby mall and Newbury Street. For quick business trips, I prefer The Bostonian.
Dining in Boston: Although Boston might not be widely known for its food scene, it has some truly great dining options, especially if you’re a fan of seafood like lobster and crab. The North End is the go-to spot for Italian cuisine, with Lucca’s being a favorite for a fancy sit-down meal, and Fillipo offering a more family-friendly atmosphere. For an authentic slice of pizza, Regina’s is a must-try—perfect for a quick pick-up to enjoy on the go or at a nearby park where kids can play.
While in the North End, don’t miss dessert at Modern Bakery or the legendary cannoli at Mike’s Pastry (cash only). The nearby park is a lovely spot to enjoy your treats and let the kids burn off some energy.
Things to Do: Boston is brimming with activities. The Freedom Trail, a 2.5-mile-long brick path, takes you through some of the city’s most significant historic sites. It goes through the North End, so while you’re grabbing a bite to eat, make sure you also check out the Paul Revere House, it is one of the American Revolution’s most famous figures. My kids loved the New England Aquarium, the Boston Children’s Museum, and the MIT Museum, which offers hands-on exhibits that are both educational and fun. For more history, the Boston Tea Party Ship and Museum is a hit with kids, featuring a reenactment of the Boston Tea Party that ties in with what they’ll learn in school.
Exploring Beyond Boston: Renting a car to explore beyond Boston is definitely worthwhile. Harvard University is a short drive away, offering a beautiful campus with a rich history. Don’t forget to rub the toe of John Harvard’s statue for good luck!
A visit to Plymouth, where you can see the original Plymouth Rock and tour a replica of the Mayflower, is another great option. The Plimoth Patuxet Museum, formerly known as Plymouth Plantation, is a hands-on experience with live actors portraying life in the early settlement. My kids have vivid memories of this place and always ask to return. The museum shop has some of the best New England cranberry products, and there’s a charming ice cream shop nearby.
If you’re up for a longer drive, Cape Cod is just a short distance away. We stayed at the Wequassett Inn, which offers both a main hotel and individual waterfront cottages. The decor is quintessential New England, and there’s even a playground and swimming pool for the kids. The inn’s dinners are elegant, featuring farm-fresh ingredients. We spent a day exploring Provincetown, a quaint town with a rich history, great coffee shops, bakeries, and unique boutiques. It’s reminiscent of Saugatuck, MI, with its homey feel.
While in Cape Cod, you can also visit Hyannis Port to see the Kennedy Compound and other beautiful homes. From there, you can take a ferry to Martha’s Vineyard or Nantucket. Both islands are stunning and worth visiting. If you plan to bring your car, book your ferry ticket as soon as the schedule is released in January, especially for summer travel, as tickets sell out quickly. Otherwise, you can usually find same-day tickets if you’re not bringing a car.
Back in Boston: Newbury Street is a must-visit for shopping, offering a mix of well-known brands and unique boutiques. The street leads to Boston Common, a beautiful park with a large pond and walking trails—perfect for a picnic with treats from The Thinking Cup, a charming coffee shop with great food and pastries.
For a special experience, consider afternoon tea at the Boston Public Library’s Courtyard Tea Room. Walking through the historic library to reach the tea room is an experience in itself. The setting is exquisite, and the menu caters to both adults and children. The kids loved the tea service, which included a little history card and activities to keep them engaged.
Quincy Market is another must-visit, offering a wide variety of food vendors under one historic roof. Whether you’re craving Italian, seafood, or sweets, there’s something for everyone. We love grabbing a little bit of everything and enjoying a picnic-style meal at one of the market’s tables.
Nightlife and More: Boston’s nightlife is lively, with historic pubs, clubs, and live theater. If you’re a baseball fan, a visit to Fenway Park is a must to see the iconic Green Monster. The area around Fenway is bustling with cool bars and restaurants. I was lucky enough to attend a private event at Fenway, where we toured the park and saw the team’s trophies up close before heading to the House of Blues across the street for live music and great food.
Boston is a city with something for everyone—rich in history, full of activities, and offering a warm, welcoming atmosphere. It’s a destination that I always look forward to visiting.