Boston is full of history and idiosyncratic charm, with its architectural treasures, narrow streets, drivers who view motor-vehicle laws as more akin to suggestions, and miles of red-brick, cobblestone, and cracked and broken sidewalks. It can also be a trial for moms, dads, or nannies pushing strollers. We quizzed a number of families about some of the most and least stroller-friendly destinations in and around the city. Here’s what they had to say:

Castle Island

The recreation area in South Boston was named as a favorite of many families, because there are lots of paved paths and walkways, plenty of green space for frolicking and picnicking, a couple of small beaches, and even an inexpensive eatery for those who are either too tired or forget to bring lunch. Tasha Brown, who lives in Dorchester with her three children, Daniella, 24 months, Tristan, 8, and Tahja, 11, likes Castle Island because it’s all encompassing. “Well, the walking paths are smooth, and that’s a must with a stroller,” Brown says. “And you have just about everything any young kid would want in a warm weather spot — there’s beach, fun food, playgrounds. And they really are all easy to get around. Even if I wasn’t here with my two older kids to help, if it was just me and the baby, she and I could still get around this park easily.” If there are downsides to Castle Island, it’s the long parking lot that can make lugging accessories like diaper bags and beach bags from car to play areas a major, exhausting chore. And it’s not easy to reach the island on public transportation.

Beacon Hill

This small, historic neighborhood exudes charm. But if you’re a mom or a nanny with a stroller, it can be a nightmare. Many tell us that while Beacon Hill is home to a couple of nice parks and playgrounds, getting to them with a stroller can be about as easy as climbing a rugged wilderness path. The downsides first: narrow sidewalks, extreme uphill walks, and a lack of parking. Haley Gerber, a nanny, demonstrated that difficulty, when we encountered her powering a stroller carrying 15-month-old Lyla DiPietro up a 45-degree slope to get to a playground. “It’s a great neighborhood in a sense,” Gerber said. “But the cobblestone? The tiny sidewalks? If you’re not in great condition, this neighborhood can either get you in shape, walking around with a stroller, or it can break you!” The most common complaint we heard? The area’s narrow sidewalks sometimes force those with wider strollers into the street, because they just won’t fit — a dangerous proposition, what with vehicle traffic. On the upside, our moms loved the play areas, Myrtle Street Playground chief among them. Its equipment is toddler friendly. The fence separating it from the sidewalk and street is sturdy, well-painted, and not at all rusty or jagged.

Faneuil Hall Marketplace

Most families agree that Faneuil Hall Marketplace — which includes North and South markets, Quincy Market, and Faneuil Hall — is a mixed bag. All love the many and varied shopping options — dads and moms can take turns breaking away to browse. Noel Porter and Mohammed Jawado of Hyde Park say taking turns is the main reason they take their infant son, Tyree, there. “I feel better leaving him with the baby for a few minutes at a time and knowing that he’s not going to struggle to get around,” Porter said. Another draw is the range of dining options, from actual restaurants (including that old Boston favorite Durgin Park) to the eclectic food court. Kids of all ages love the street musicians, jugglers, and acrobats who perform throughout the day. But for families with strollers there are issues. The area is paved with a mix of stone and brick, which are fine for sturdier or jogging strollers, but it can be a hassle for those with lightweight umbrella strollers. Also note that in warm weather the marketplace gets quite crowded so you’ll need to keep a close eye on wandering toddlers. Jawado said, “Sometimes the people can make or break it. And here, if it’s too crowded it can be miserable.” Street parking around the marketplace is limited and very expensive, but there is plenty of public transportation nearby.

Drumlin Farm