By MICHAEL BAGINSKI/ Boston wears it’s history on it’s sleeve, even if it’s most obvious in its iconic landmarks and distinguished architecture. But the city, which is preparing to celebrate its 400th birthday in 2030, is, in fact, so much more: a combination of history and modernity, America’s most European city, and a democratic bastion at a time when it means more than ever.
Ever evolving, Boston is a big city that nevertheless feels small. As such, it’s eminently walkable, but also hike-able, jog-able and bike-able through countless parks and revered “third spaces” that are free to the public – and where river and ocean water environments (both on and adjacent) are treated as public treasures, not coveted commercial opportunities.
It’s a city that takes pride in its immigrant communities and the varied food culture they contribute to; and notably organized a defiant collective response to early-day ICE incursions through app warnings and citizens blowing whistles, prompting flash mob gatherings to protect victims. Simply put In the words of one resident, “making it as uncomfortable for them (ICE agents) as possible.”
It’s an enthusiastic sports town – from the historic Red Sox to bragging rights as the indisputably best host city for the recent FIFA World Cup; but also, a refined centre of culture – from plentiful public art to the renowned institutions like the Museum of Fine Arts, and the eminent Boston Public Library (known not just for its books, but its educational classes and high tea) to dozens of neighbourhood bookstores.
There are both grand festivals and “hiding holes” – small enclaves, cafés, pubs, that make you feel like you’re discovering something.
The Massachusetts Institute of Technology (MIT) and Harvard generate energy and innovation, contrasted by reflection and solitude in leafy, historic neighbourhoods like Beacon Hill. Or social gathering spots like Faneuil Hall/Quincy Market and the authentic Italian restaurants, cafés and ice cream shops of North Boston.
Spectacular in spring, wonderful in summer, and fabulous in fall foliage season (Sept.- Nov.), steps are being taken to boost winter offerings and activations (such as ice skating and the launch of ‘Frostival,’ the city’s new winter celebration) for visitors and residents to ensure the city’s reputation as a bona fide four-season destination.
And that includes Canadians, who are welcomed with open arms.
“We were making jokes that when Trump said he wanted Canada to join they U.S., we said we’d rather join Canada,” laughed one Bostonian.
Canadian FAM
Meet Boston, the city’s primary tourism marketing organization, recently co-hosted a select group of 10 leading Canadian travel trade professionals, meeting planners (and Travel Industry Today), recently for an immersive four-day FAM trip designed to showcase the vast breadth of leisure experiences in the New England capital.
Recognizing Canada as Boston’s top international visitor market with more than 658,000 visitors in 2025, the initiative nevertheless was a proactive response to the downturn in visitors from this country to the U.S., with Emily Meehan of Meet Boston stating, “We have really seen and felt the missing of our Canadians visitors; we really do love (them).”
Nik Pereira, Sr. VP, Meet Boston, added, “Canada remains a key market for Boston, and this FAM was a valuable opportunity to showcase the new experiences, venues, and developments shaping the destination today, while highlighting the energy and vibrancy of Boston.
“These FAMs, together with our partnership with (Canadian representative) DCI, represent a robust, dedicated and multifaceted effort to grow our market share of Canadian visitors, particularly amidst trade and geopolitical challenges. With expanded air service, exciting new offerings and strong momentum following a landmark year for the city, there has never been a better time for Canadians to discover – or rediscover – Boston.”
Throughout the four-day program, FAM participants got to experience the city through a curated itinerary developed with Meet Boston’s tourism partners, with a highlight being a Red Sox versus Blue Jays game at historic Fenway Park.
Among itinerary highlights:
- Cultural and historical highlights included guided explorations of the Seaport District with the Boston History Company, visits to the Museum of Fine Arts Boston, including the reimagined 18th-century Art of the Americas galleries, and time spent discovering Beacon Hill, Cambridge Squares and the MIT campus and the Innovation Trail.
- Culinary experiences showcased the city’s diverse food scene through a hands-on noodle-making class at Michelin-rated PAGU, local tastings with City Brew Tours, and dining experiences at iconic establishments including a Sam Adams beer pairing dinner at Parker’s Bar at Omni Parker House and The Banks Fish House.
- Participants also engaged in active and waterfront experiences, including a Boston Harbor cruise at sunset aboard Yacht Hope with Charles River Boat Company, cycling tours with Urban AdvenTours, and sweeping city views from VIEW Boston.
- At the Omni Boston Hotel at the Seaport, guests experienced the energy of Boston’s modern waterfront district through contemporary accommodations, seven distinctive dining options, a rooftop pool, vibrant amenities, and Breve Spa, the hotel’s full-service luxury spa, while the newly renovated Omni Parker House (the oldest operating hotel in the U.S. and home of the Boston Cream Pie in 1856) offered a glimpse into the city’s storied past with refreshed guest spaces and timeless elegance in the heart of Downtown Boston.
There’s no doubt the FAM participants were impressed.
G Adventures VP and Managing Director Canada David Green said, “I’ll be honest, I’ve always liked Boston when I’ve visited for work, and in the past I’ve of course visited the Cheers Bar and been on the Duck tour like every other visitor! But this time felt different.
“My highlight on this visit was getting outside the city centre and participating in a couple of historic walking tours and a local cycling tour. We covered a lot of mileage and had incredible local guides who impressed us with both their local knowledge and their passion for Boston. Daniel the owner from the Boston History Company was on another level!
“We also got to see Boston from the water! I thoroughly recommend taking in the sights from one of the many boat tours, perhaps with a lobster roll and a local beer. Another food highlight was our visit to PAGU, where we made hand-pulled noodles and met Tracy, the inspirational owner who shared her story with us.”
Siobhan Chretien, Sr. Director, Tourism for DCI, simply enthused, “There are just endless pretty streets,” adding, “We’ve yet to see an area that’s not lovely.”
Greta Kamaterou of TRAVELSAVERS remarked, “World-class museums, remarkable architecture, beautiful parks, vibrant neighbourhoods like the Seaport, unforgettable food, and some of the friendliest people you’ll meet – Boston truly has it all, said
“Just one warning,” she added. “You may arrive planning a weekend and leave wondering how soon you can come back.”
TIT’s take
Five things* we recommend:
- Fenway frenzy: Go to a game at the historic ballpark – home of the Red Sox and the oldest stadium in major league baseball – for an atmosphere unlike any other. Even non-ball fans will enjoy.
- Food glorious food: From lobster rolls to local popovers, clam chowder and pizza, a food tour is a great way to see and get a taste of the city. Locals recommend Yankee Lobster in the Seaport District for lobster rolls.
- There has to be history: Considered by many the best walking tours in the city, Boston History Company covers all the bases with unique insight and passion, from the Boston Tea Party to the Boston Massacre, (mob boss) Whitey Bulger, and the Big Dig freeway removal. “Every fact has to have a story,” says company owner Daniel Berger-Jones.
- Cycle of life: Walk for sure, even it’s just around Boston Common or along the Freedom Trail, or on some of the 75 km of waterfront paths, but a good bike tour (photo above) covers more ground in less time. Urban AdvenTours did a great job and with a high emphasis on safety.
- Pubs a plenty: Boston is a pub town. But skip touristy Cheers, and try the Green Dragon Tavern, The Bell in Hand (oldest tavern in the U.S., operating since 1775), Union Oyster House, or, for fish & chips and a Guinness, the excellent The Dubliner, which gained international fame this summer as home base for Scotland’s Tartan Army during the World Cup (always trust a Scot to find the best pub). Or find your own.
*6: Beyond Boston: Cape Cod (south) is a popular excursion, but closer and every bit as compelling is the North of Boston region, which includes spectacular coastal scenery as well Salem (witch trials), Rockport (arts scene) and Gloucester (quaint fishing village, also featured in the Wicked Tuna TV show).
Getting there
Boston continues to be one of the most accessible U.S. destinations for Canadian travellers, supported by robust year-round air service from key Canadian gateways. The city is served by multiple daily non-stop flights from Toronto Pearson and Billy Bishop airports, as well as Montréal, while direct air service is also available from Calgary, Ottawa, Québec City, and Halifax.
Upcoming
- Open Newbury Street (select Sundays through Oct. 11) see the popular street become pedestrian-only on select Sundays, allowing visitors to explore one of the city’s most vibrant shopping and dining districts car-free.
- Head of the Charles Regatta (Oct. 16-18) takes over the Charles River with the world’s largest three-day rowing event, attracting more than 11,000 athletes and hundreds of thousands of spectators.
- Boston Book Festival (Oct. 17) is one of New England’s premier literary events at Copley Square with author talks, readings and cultural programming.
The bottom line
“So, here’s the thing,” G Adventures’ Green concluded. “Travel to the US from Canada is currently down for all the known reasons. The current political tensions are understandably driving Canadians away from the US. But on this trip, I’m reminded that we are indeed great neighbours. Everyone I met was warm and welcoming and grateful for our visit…
“While we might have issues with the U.S. Administration, I’m reminded that all the US citizens I met were very thankful for our visit, and they love Canadians! I loved my time in Boston and can’t wait to visit again.”
Shae Goldberg of WorldStrides agreed. “At home we see things on the news and we can fall into a trap,” she said. “When you’re here, all that goes away.”
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