A Boston Family Vacation: One Wheelchair, Three Kids, and a Whole Lot of Joy

For Jenn Allen, who runs the disability-focused travel blog Wonders Within Reach, Boston was an obvious pick for a family getaway. The city’s reputation for accessible transit and well-designed streets made it a safe bet for her five-year-old son Jaden, who uses a wheelchair. She’d recently had a great experience with Old Town Trolley in Nashville—their accessible trolleys were a smooth ride for Jaden—and the same company operates in Boston. Plus, Jaden and his older brother Wesley are history buffs. So Jenn packed up her three kids (Nella, 4, Jaden, 5, and Wesley, 8), along with her sister, and drove the minivan into the city. She had a trolley booked, a hotel reserved, and a plan for the Boston Tea Party Ships. Everything else, she figured, they’d figure out on the fly. That looseness turned out to be a gift.

Boston’s accessibility isn’t just talk. The central playground has poured rubber surfaces instead of mulch, and a ramp connects both levels so kids with mobility needs can play everywhere. The Freedom Trail’s less-accessible spots are clearly flagged online. “Accessibility info online is a rare treat,” Jenn says. Her strategy: anchor the trip around one sure thing—the accessible trolley—and one hopeful thing: the Tea Party Ships. From there, she let the rest unfold. Driving from Lancaster, Pennsylvania, gave them a safety net; Jaden’s wheelchair holds medical supplies, and flying is a hassle. In Massachusetts, any metered space is free with a handicap placard, so parking was never a problem.

The first real hiccup came at the hotel. Jenn booked the Fairfield Inn Boston Dedham online, assuming an accessible room would work. It didn’t. The bathroom door couldn’t close with the wheelchair inside, and navigating the room meant crawling over the bed. They switched to the Four Points by Sheraton Norwood, where spacious rooms, a welcoming staff, and a pool made all the difference. Jenn’s lesson: call ahead and ask if a wheelchair fits through the bathroom door, and whether the accessible room has more than one bed. The rest of the trip was a series of small victories. At the Children’s Museum, Jaden used a pulley to lift his own body weight—something his arm strength from wheeling made effortless. “I loved seeing his joy,” Jenn says. At Ristorante Saraceno in the North End, the staff made them feel genuinely welcome, not like a burden. And Jaden’s favorite spot? The Public Garden, where he sat on a wall watching ducks. “An accessible space where a family can unwind without barriers is a rare treat,” Jenn says.

Jenn’s advice for other families: start small. Boston is a good first city for wheelchair users because its inclusion efforts are real, and problems are recoverable. Download the GoWhee app to find accessible playgrounds. Filter Google Maps for accessible routes. Book the Old Town Trolley for at least a day—it covers the city and accommodates wheelchairs without advance notice. And leave room for the unplanned: a pulley, some ducks, a restaurant that makes you feel like you belong. “Everything feels overwhelming when it’s the first time,” she says. “The only way to know what you’re capable of is to try.”