This trip is special. The women in my family are heading to Boston, and I cannot contain my excitement for one more second. Boston has been on our list for years, and this time, we actually booked it. My mom, sister, cousin, and aunt will spend six days in an extraordinary city, with more history, food, and adventure than we can probably handle. We are still ironing out the final details, but here’s what we’re thinking, and why you should steal this itinerary for yourself for a Boston travel adeventure.
Boston is one of those rare cities that delivers for every kind of traveler. History, world-class food, sports, culture, architecture, it’s all here, packed into a compact, walkable city that somehow never feels overwhelming. As the history nerd in the group, I feel so lucky to visit the city where our country began in the same year that we celebrate our 250th anniversary!
If you’ve been on the fence, let me make it simple: go.
I grew up traveling with wheelchair users long before the ADA existed, back when accessibility was an afterthought and “accessible room” was optimistic at best. We traveled anyway. Over the years accessible travel has been a focus for me. I’ve planned trips for clients traveling with service dogs, children on the autism spectrum, and travelers managing serious health needs including dialysis, and every trip has made me better at this.
But this one is personal. This trip carries the two most important women in my life, both wheelchair users. And here’s the thing about my family, if something isn’t right, they will tell me. Immediately. In detail. And they will be completely right to do so. (Don’t tell them I said that last part)
I have been diligent. Every hotel has been vetted beyond ADA compliance on paper, roll-in showers confirmed and turning radius checked. Every attraction has been called. Every transportation booking has accessibility needs noted at reservation, with follow up emails and phone calls. We are not about to be told we can’t access something we want to see!
We’re landing at Logan and heading straight to Beacon Hill. No agenda, no checklist — just drop the bags and walk. Beacon Hill’s gas-lit brick streets and famous Acorn Street are best discovered slowly. We’ll end the evening with a stroll through Boston Common, the oldest public park in America, before finding dinner in the Back Bay.
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, it promises to be far more thrilling than it sounds.
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 to Bunker Hill Monument and the USS Constitution- still an active U.S. Navy vessel.
Our plan is to wear good shoes, bring water, and stop for a cannoli in the North End when we pass through.
The Boston Tea Party Ships and Museum is supposed to be the most fun one can have in a museum. We will be assigned a colonial identity, attend a town meeting, board replica ships, and throw tea into the harbor while actors in full period costume argue around you. Completely immersive and genuinely unforgettable. I hope I get to throw the tea overboard!!
Afternoon is for the Seaport District, one of Boston’s most exciting newer neighborhoods, with a walk along the Harborwalk and a stop at the stunning Institute of Contemporary Art before dinner by the water.
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 will doing the morning tour of Fenway first warning track, press box, Green Monster seats, then watching a 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 will be immersing ourselves in all things Kennedy! I think I have read almost every book, biographer and memoir about all of the 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.
Afternoon across the Charles River into Cambridge for Harvard Square, the campus, and the Harvard Art Museums. Then a long, celebratory last dinner before heading back for our final night in the city.
We still have quite a list of things to see ( see below), but we only have one more day. What would you choose?
Museum of Fine Arts — one of the largest art museums in the country, with a world-class Impressionist collection and Egyptian artifacts that stop you cold.
Isabella Stewart Gardner Museum, which is one of the strangest and most wonderful places in Boston. A Venetian palazzo built in the Fenway neighborhood, filled with a legendary private art collection arranged exactly as Isabella left it, unchangeable by the terms of her will. The site of the largest unsolved art theft in history, the empty frames still hang where the stolen paintings once were. Unmissable.
Martha’s Vineyard — 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. Six distinct towns, each with its own personality — the stately sea captains’ mansions of Edgartown, the explosion of gingerbread Victorian cottages in Oak Bluffs, 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. A day trip that earns a place in your memory permanently.
Salem & the Witch Trials — Salem is not what you expect, and it is better than you’ve been told. In 1692, in a period of collective fear and hysteria that lasted less than a year, nineteen people were hanged and one pressed to death on accusations of witchcraft — most of them ordinary neighbors, farmers, and churchgoers. 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.
The Underground Railroad — Boston was one of the most active cities in the abolitionist movement, and the history is written into the streets if you know where to look. The Black Heritage Trail on Beacon Hill — a 1.6-mile walking route — connects fourteen sites tied to Boston’s free Black community and the Underground Railroad, including the African Meeting House, the oldest surviving Black church in America, and the homes of freedom fighters who sheltered escaped enslaved people at enormous personal risk. The Museum of African American History, which anchors the trail, tells this story with the depth and honesty it demands. This is not a footnote to Boston history. It is Boston history.
Boston, we are coming for you, history, chowder, Fenway and all. Follow along here on the Sunshine Escapes Travel blog, to see how our adventure unfolds or message me for your own personal curated travel itinerary
