We were landing at Logan and dropping the bags at our hotel. The accessible rooms were genuinely accessible. The request for a roll-in shower was granted, and everything seemed to be off to a good start. So we decided to go drive around and get a lay of the land before our dinner reservation. But first, we had to survive the journey to the city center, which means my cousin deserves a literal Congressional Medal of Honor for her heroic feats behind the wheel.

Because we were traveling with two wheelchair users, renting a minivan made sense. Driving in Boston is not for the faint of heart. Boston's roads weren’t designed for cars; they were designed for 17th-century cows, resulting in a chaotic spaghetti map of one-way labyrinths, missing street signs, and aggressive local drivers who view turn signals as weakness. Navigating that madness while dodging rogue pedestrians and decoding GPS instructions that come three seconds too late requires nerves of absolute steel.

Yet, she conquered the asphalt jungle flawlessly, delivering us safely to our destination, the Union Oyster House. Having served hungry diners continuously since 1826, it is officially the oldest continuously operating restaurant in the United States and the perfect place to raise a glass to the start of our Boston adventure.

For this trip, every single supplier—hotels, tour operators, transportation companies, attractions—was contacted multiple times before departure. Not because I doubted them the first time, but because experience has taught me that accessibility is one of those things that can fall through the cracks between a booking agent and an operations team.

Several attractions have done extraordinary work to ensure inclusive entry. Staff at a number of stops were warm, prepared, and clearly briefed. These moments matter and deserve to be acknowledged. On this day, we did the hop-on, hop-off bus tour, had reservations for the Boston Tea Party reenactment, and were planning on ending the night on a sunset cruise in the harbor.

We had planned on staying on the bus for the entire loop and getting off at the last stop. However, some of our group really wanted to go to the "Cheers" bar, so we decided to get off at the second-to-last stop. This is where we ran into our first snafu: the bus lift had never been tested. This was the hardest moment of the trip. A tour company, one that had been called multiple times, confirmed multiple times, and assured us multiple times that they could “absolutely” accommodate multiple wheelchair users, sent a bus (they only have two buses in their fleet that have a lift) with a lift that had not been tested before departure. When the moment came to deploy it, it didn’t work. Family members sat on the bus while the rest of the passengers waited outside. The discomfort, the self-consciousness, the helplessness of that moment is not something anyone on a vacation should ever have to feel. This same company has a dedicated spot to secure a wheelchair for transport; it requires the bus seats to be flipped up against the wall/window, preventing a wheelchair user from seeing out the window.

A replacement bus eventually arrived. The tour continued. But those minutes, sitting there, aware that everyone was waiting, aware that this moment had been entirely preventable, are not forgotten.

Once off the bus, we ran into snafu number two: the ramp into the "Cheers" bar was too steep to be safe.

Several ramps we encountered were well outside ADA compliance standards, with dangerously steep grades that required significant upper-body strength or a second person to navigate safely. They exist on paper as “accessible.” In practice, they are hazardous. Marked as accessible on maps and in listings, these ramps create a false sense of security that can put wheelchair users in genuinely risky situations.

To someone who has never pushed a wheelchair up or down a ramp, there is nothing wrong with this picture. However, those of us who have can immediately tell that this ramp is dangerous.

The next issue we ran into was at Boston Common. This park had numerous entrances, most with steps. One of Boston’s most beloved green spaces had dozens of entry and exit points around its perimeter, and all but two of them featured steps. Finding those two accessible gates required significant additional walking, sometimes covering the full length of a city block or more in the wrong direction before backtracking. There was no clear signage directing wheelchair users to the correct entrances. You simply had to know, or walk until you found out.

While I am pointing out issues that we encountered, this day was still awesome. Unfortunately, we are accustomed to these types of obstacles, and we have learned to roll with it, never losing our sense of humor, our determination to see it all, and our enthusiasm for the task at hand.

On this day, we split up by interests. Two of us head to a Red Sox game, and this is certainly a highlight! There are baseball stadiums, and then there is Fenway Park. Opened in 1912, it’s the oldest active Major League ballpark in America, and being inside it feels almost sacred. Some of our group are huge baseball fans, so they do the morning tour of Fenway first—warning track, press box, Green Monster seats—then watch the game.

I hear “Sweet Caroline” in the eighth inning, with the whole crowd singing together, is one of those experiences that makes you briefly certain everything in the world is exactly right.

While some are at Fenway, the rest of us are immersing ourselves in all things Kennedy! I think I have read almost every book, biography, and memoir about the entire Kennedy clan, and I cannot wait to see where they got their start and the first house they called “home.”

The JFK Presidential Library on Columbia Point is said to be one of the finest presidential museums in the country: emotionally honest, beautifully designed by I.M. Pei, with sweeping harbor views that take your breath away.

In the afternoon, we head across the Charles River into Cambridge for Harvard Square, the campus, and the Harvard Art Museums. Then a long, celebratory final dinner before heading back for our last night in the city.

Just 45 minutes by ferry from Woods Hole, Martha’s Vineyard is one of those places that feels like the rest of the world agreed to slow down and leave it alone. The pace here is a beautifully relaxed contrast to the frantic energy of Boston, though it shares the same historic DNA—meaning the streets are deeply weathered, and the ancient buildings almost always feature a few steps to get inside. Some entryways were low enough to easily "pop" the chair up and into, while others presented a much steeper historic hurdle. Yet navigating those thresholds is part of exploring its six distinct towns, each with its own undeniable personality—the stately sea captains’ mansions of Edgartown, the explosion of gingerbread Victorian cottages in Oak Bluffs, and the working fishing docks of Menemsha. The island has drawn artists, presidents, and wanderers for over a century, and the moment the ferry pulls into the harbor and that salt air hits you, you’ll understand exactly why. It’s a day trip that earns a place in your memory permanently.

However, we ended this part of our adventure with some of our group getting stuck in the ferry elevator. The elevator was small, and only one wheelchair user and another person could fit, so our first two people took it down to the parking deck. Then the elevator stopped working. My mom and my sister were stuck up on the third deck, and they couldn't get the elevator to work. Multiple crew members tried to assist, but no one could board the ferry until they were off the ship, so everything stood still until someone could get the elevator working. After about 30 minutes, it started working, but nothing is more nerve-wracking than getting into an elevator, because you have no other choice, and not knowing if it will actually let you out at the bottom. Luckily, it safely got our last two family members to the parking level so they could exit the ferry.

This one is non-negotiable. The Freedom Trail is a 2.5-mile red line painted through the city, connecting sixteen of the most significant historic sites in America, and it promises to be far more thrilling than it sounds. Staff with this tour company were warm, prepared, and clearly briefed. These moments matter and deserve to be acknowledged.

Highlights include the Massachusetts State House, the Granary Burying Ground (Paul Revere, Samuel Adams, and John Hancock are all buried here), the Old South Meeting House, where the Tea Party decision was made, Old North Church, and finally, across the Charlestown Bridge, the Bunker Hill Monument and the USS Constitution—still an active U.S. Navy vessel. Our plan was to wear good shoes, bring water, and stop for a cannoli in the North End when we pass through.

Salem is not what you expect, and it is better than you’ve been told. In 1692, during a period of collective fear and hysteria that lasted less than a year, nineteen people were hanged and one was pressed to death on accusations of witchcraft—most of them ordinary neighbors, farmers, and churchgoers.

After our Freedom Trail tour, we headed out of town to Salem, where we did the walking tour of the history of the Salem witch trials. They provided additional staff to assist with spotting curb cuts and identifying the most accessible routes, and they had clearly walked the tour with a wheelchair in mind prior to our arrival.

The Salem Witch Museum brings the original trial testimony to life with a gravity that silences even the most distracted visitor. Proctor’s Ledge Memorial, where the executions took place, is a quiet, devastating patch of ground with the names of the condemned carved into granite.

Salem refuses to let you look away from what happened here—and it shouldn’t. History this uncomfortable is history worth sitting with.