The Perfect Getaway: A family-friendly long weekend in Boston
Discover this charming New England metropolis, known for its role in the American Revolution, brick row house-lined neighborhoods, museums, and beautiful Public Garden.
By Tanvi Chheda | June 27, 2025 (Updated October 17, 2025)
First settled as a Puritan colony and later a site of rebellion against the British, Boston is a must visit for families interested in U.S. history. But there’s more to Beantown than just its fascinating past. From art museums to baseball games, there’s something for visitors of all ages to enjoy. Here are our suggestions for a family-friendly and fun-filled weekend getaway in Boston.
Friday
Morning
Welcome to Boston! Settle into your home away from home, Pennyweight Hotel Boston, Curio Collection by Hilton. Located in downtown, this hotel is the perfect home base close to several historical sites, as well as Quincy Market, a busy hub of eateries and shops. The hotel’s elegant lobby-level lounge, swathed in coral and green hues, feels contemporary and timeless all at once. Spacious, whitewashed rooms, only 112 in total, feature fireplaces and sleek black-and-white bathrooms.
Afternoon
Get a lay of the land by joining Boston’s famous Duck Tours. You’ll see the city by land and water aboard a brightly painted amphibious vehicle that passes several major landmarks before heading into the Charles River. After the tour, head up to View Boston, a 360-degree observation deck on the 52nd floor of the Prudential Center. You can also enjoy the bird’s-eye view of the city while enjoying lunch at The Beacon Bistro located on the same floor.
Evening
It’s been a long day so take some time to rest and recharge in your cozy room. When dinnertime rolls around, a tasty, kid-approved meal is just steps away at 155 on Portland. Located in the hotel lobby, this restaurant serves up classic American pub fare with some elevated twists for the parents — think burgers and fries alongside calamari and flavorful pasta. If the weather is cooperating, be sure to grab a seat on the outdoor patio.
Saturday
Morning
Fuel up with breakfast at Theo’s Cozy Corner Restaurant, just a 10-minute walk from your hotel. Next, take a deep dive into Boston’s role in the American Revolution with a guided tour through the Freedom Trail Foundation (best for upper-elementary age and older). The 90-minute, 1-mile (1.6-kilometer) walking tour includes stops at sites such as the Granary Burying Ground and Paul Revere House. For families with younger kids, consider exploring the interactive, play-based exhibits at the Boston Children’s Museum.
Afternoon
Make your way to the Boston Tea Party Ships & Museum for one of the city’s most unique activities. Experience the Boston Tea Party firsthand as a costumed guide leads you through 3D reenactment halls to the deck of the ship at Griffin’s Wharf, where the infamous rebellion occurred more than 250 years ago. The best part of any visit? Throwing tea overboard (and then reeling it back in) from a replica 18th-century ship.
Evening
Explore Boston’s Back Bay neighborhood with a stroll along café- and boutique-lined Newbury Street, popping into stores that pique your interest. When it’s time for dinner, hit gorgeous rooftop restaurant Contessa for the delectable squash carpaccio with agrodolce and arugula or the Parmesan-topped fusilli Genovese. Wash it all down with Negronis for the adults and Shirley Temples for the kiddos.
Sunday
Morning
Start your day with breakfast at 155 on Portland before heading to the Museum of Fine Arts, where the whole crew can admire masterpieces by Rembrandt, Degas, and van Gogh. Among the highlights is the museum’s sizeable Japanese art collection, including some 45,000 woodblock prints. The museum frequently offers drop-in family activities, such as dry printmaking, so be sure to check the program calendar ahead of your visit.
Afternoon
Hop in a taxi or take a 20-minute walk through the Emerald Necklace chain of parks to reach Time Out Market Boston. This food hall has 15 vendors, making lunch easy with options everyone in your crew will enjoy, such as tacos, burgers, pizza, sushi, and more. Finish with a yummy treat from Union Square Donuts. The chocolate-topped Boston Cream donut is a can’t-miss classic.
Evening
Regardless of where your team loyalties may lie, catching a ball game at the legendary Fenway Park is a must. The 37,755-seat stadium, where baseball stars such as Babe Ruth and Ted Williams have played, dates back to 1912 and remains largely unchanged. True baseball fanatics should also buy tickets for a stadium tour before the first pitch. When the family gets hungry, grab a Fenway Frank, the quintessential Boston hot dog.
Monday
Morning
Grab breakfast and your next read at the adorable Beacon Hill Books & Cafe before strolling over to the beautiful Boston Public Garden, the first botanical garden in the country. Along with manicured paths, sculptures, and statues, the green space is known for its small fleet of swan-shaped pontoon boats that glide along a 4-acre (1.6-hectare) man-made lagoon. Families with younger children shouldn’t miss the darling duckling statues from Robert McCloskey’s beloved picture book, “Make Way for Ducklings.”
Afternoon
Visiting between May and October? Hop on a whale-watching tour with Boston Harbor City Cruises to spot these enormous mammals, including humpbacks, finbacks, and minkes. Outside of whale-watching season, the company also offers a Winter Wildlife Cruise. Either way, you’ll enjoy impeccable views of the city. After the tour, fuel up for your trip home with a waterfront lunch at The Barking Crab, a local favorite serving fresh seafood.
Until next time!
After a weekend of museums, parks, history, and more, there’s no doubt your family is leaving Boston with memories to last a lifetime. In a city as dynamic as Boston, a return trip is a must, so don’t hesitate to start planning your next visit before you make it home from this incredible trip.
Tanvi Chheda
Formerly an assistant editor at Travel + Leisure, Los Angeles-based Tanvi Chheda has been freelancing for 15 years now. She writes mostly about lifestyle and travel, which often spills into arts & culture, food, design, and more. With two young children, family travel is also a passion of hers. Given her South Asian heritage, she writes about India quite frequently as well (she was born in India and speaks three Indian languages). When not traveling or writing, she enjoys reading, cooking, and spending time outdoors. Her work has appeared in the New York Times, the Wall Street Journal, AFAR, Virtuoso Life, Four Seasons magazine, Qantas, Inspirato, Invited, Pasadena magazine, OLTRE, and Ciao Bambino, among others.
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