Life and travel can be funny sometimes.
In the past 13 years, I’ve probably been to a couple hundred destinations around the world, from Thailand to Tahiti and Scotland to Saint Lucia. I’d been all over the globe, but somehow I forgot about one of the great cities a mere 10-hour drive from my home in Toronto.
My wife and I visited Boston before we had our first child, and I thought it was terrific. A few years later I became one of the Toronto Star’s baseball writers, which allowed me to cover Blue Jays’ games at Boston’s fabled Fenway Park. We usually had a few hours of free time in the morning (this was before the Internet), so I would wander around Back Bay and the Boston Common, checking out nice coffee shops and taking walks in the park.
As the outgoing Toronto Star travel editor, I spent a few days in Boston back in 2013; enjoying fine meals in the city and nearby Cambridge, taking a tour of historic sites, and checking out a fine art museum near Fenway.
Boston Common and downtown Boston. Meet Boston Photo
I hadn’t been back since, and I wasn’t sure what to expect when we rolled into town on a recent car trip. What I found was a truly spectacular city, with tons of cool neighbourhoods, amazing parks, divine food and a palpable sense of energy. It was like a wake-up call; a cold shower on a frigid January day.
On our last night in town, following a truly spectacular meal at Kaia restaurant in the South End, I turned to my wife in the car and said. “I had forgotten how great this city is.”
She nodded in agreement, and I have a feeling we won’t wait another 13 years for a return visit.
With that out of the way, here’s how we spent our recent 2.5 days in Boston, which was named one of the top three cities in the U.S. this week by readers of Conde Nast Travel.
DAY ONE
A FINE HOTEL
The Royal Sonesta Hotel, Boston. Royal Sonesta Photo
We arrived at our hotel, the Royal Sonesta Boston in Cambridge, in the late afternoon. We had a spacious (and I mean spacious) room with massive windows overlooking the Charles River, with downtown Boston spread out in front of us. The hotel (see below for more details) is a popular, artsy spot for people who want to stay in Cambridge, a vibrant community of its own and also home to both Harvard University and the Massachusetts Institute of Technology.
A HEAPING HELPING OF HUNAN
The bar at Sumiao Hunan Kitchen, a fabulous spot in Cambridge, Massachusetts. Meet Boston Photo
Located in the busy and trendy Kendall Square area of Cambridge, a short walk from the Royal Sonesta, Sumiao Hunan Kitchen was packed to the rafters on a recent Thursday night. A jazz duo was playing in a corner of the restaurant, and there was a nice patio outside for a warm, late summer evening. We took the recommendations of our waiter and ordered the Beef on Fire, a large serving of shredded beef with pickled yellow pepper, bell pepper, ginger, and garlic that had a sizeable but not overpowering kick of space. The Kung Pao shrimp were plump and juicy and came with nicely cooked veggies and the Gyoza were lovely. The green beans were a small mountain with dry red pepper, peppercorn oil and pickled Sichuan yacai (the upper stem of a mustard seed plants). I don’t think I’ve had better green beans in my life. They have a nice selection of local beers, which match well with Hunan cuisine. The restaurant was given a Bib Gourmand recommendation by the MICHELIN guide in 2025.
DAY TWO
The Sports Museum in Boston. Jim Byers Photo
Following a fine breakfast at the Royal Sonesta, we took a short walk to downtown Boston to check out the The Sports Museum at TD Garden arena. The main component is Heritage Hall, which honours the rich history of the Boston Bruins NHL team. The heritage facility opened in 2024 to honour 100 years of the Bruins and features terrific, interactive features such as calling Bobby Orr’s famous goal to win the Stanley Cup. You also can have a virtual trading card made with a Bruin’s jersey or take slap shots against a goalie who looks suspiciously like a net minder of the rival Canadiens. Look for great artifacts from such Bruins’ legends as Don Cheever, pesky Brad Marchand, former coach Don Cherry and Willie O’Ree, who broke the colour barrier in the NHL in 1958. It’s slightly painful for a Maple Leafs’ fan, but a visit any hockey aficianado would likely enjoy. If you wander the halls of the arena, you’ll also find mementoes and statues of such Boston sports greats as Ted Williams, Roger Clemens Big Papi Ortiz, Larry Bird, Bill Russell (the legendary Boston Celtics’ centre who won 11 NBA championships in 13 years). And, of course, former New England Patriots QB Tom Brady, widely considered the best quarterback in NFL history. There’s also a display of gaudy (and then some) championship rings of Boston teams from over the years. It’s cool to see the arena, still known to some as the Boston Gardens, which can seat nearly 19,000 fans for a basketball game.
AN HISTORIC, GREEN WALK
Boston Common and the Massachusetts State House. Jim Byers Photo
Following our sports experience, we grabbed a coffee and took the roundabout route to the North End, where we had lunch schedule. I didn’t remember the Massachusetts State House being quite so striking. The gold dome is extremely handsome, and the building sits on a small hill near the Boston Common.
We also admired a series of small graveyards, including the one where former U.S. President Samuel Adams is buried. We stopped for a photo or three, and then rested a bit on a bench on the Common, a huge, leafy park that takes up a wide swath of downtown. We didn’t get as far as the famous swan rides, but it was a pretty morning and we loved watching the world go by under a thick canopy of trees.
From there it was up to the Rose Kennedy Greenway, a long, linear park that was created when Boston wisely buried one of its downtown expressways and gave the land over to park space. The area we checked out featured lovely gardens, umbrellas and picnic areas. It’s the sort of thing Toronto could do if it ever had the courage to tear down the monstrosity called the Gardiner Expressway. There was also a lovely, outdoor market going when we visited.
It’s only a short walk for the greenway to the North End, which is teeming with Italian restaurants and cafes.
LUNCH, A SHORT NORTH END WALK, AND LEGENDARY PASTRIES
A fine salad at Little Sage restaurant in Boston. Jim Byers Photo
We had an excellent lunch at a place in the North End called Little Sage, including lovely bluefin tuna carpaccio with pickled onion, arugula and cured olives and a fresh, bright salad with local peaches and heirloom tomatoes. That was followed by rich, luscious lobster gnocchi (we’ll diet later) and a nice serving of Lamarche pasta with pork shoulder and snap peas.
It’s a bright, modern spot with a cool, hip vibe. Following our lunch, my wife looked around the immediate area and her American-born husband wandered up the street to see the Old North Church, famous as the site where American patriot Paul Revere waved his lantern (one if by land, two if by sea) to warn of a pending British attack during the Revolutionary War.
As much as the church is worth a look, I was just as much in admiration of the cool doors and brick architecture of the surrounding homes.
I met my wife at Mike’s Pastry, a legendary Boston spot for fist-sized cannoli, cinnamon buns, pistachio croissants, and, naturally, Boston Cream Donuts. I must have spotted six or eight people wandering about town with Mike’s Pastry boxes over the next day or two, a testament to the enduring popularity of the place.
FABULOUS FENWAY
Fenway Park in Boston. Todd Kent/Unsplash Photo
I’d been to many games here as a sports reporter, but this was my first time visiting Fenway Park as a fan. I expected it to be an enjoyable experience, but I was truly overwhelmed by the palpable level of energy as I walked down Van Ness Street, just south of the ballpark.
Unlike other parks, they take your ticket before you walk down the street which means the surrounding neighbourhood is really a part of the actually ballpark. It was like being parachuted into the big top at the biggest Ringling Bros. Circus show of all time, a whirling, swirling cacophony of sound (“Go Sox,” “Get Your Program Here’) and smells (the sweet aroma of grilling onions and peppers combined with the smoky tang of hot dogs on a grill and a sea of beer).
I felt totally enveloped and wonderfully transported to a safe and vibrant world, where the only thing that mattered was that there was a baseball game about to be played and the city’s beloved Red Sox would be on the field.
When I got home I found a quote about Fenway from former major league pitcher Bill “Spaceman” Lee. “Fenway Park is a shrine,” he once said. “People go there to worship.” Amen to that.
As it turned out, we were there on Sept. 11 and it was the 25th anniversary of the 9-11 terrorist attacks. The two planes that were piloted into the World Trade Center in New York City both originated in Boston, and the Red Sox had family and friends of some of the victims throw out the first pitch en masse.
Fenway Park in Boston. Kyle Klein/Meet Boston/Boston Red Sox Photo
We had fine seats directly behind home plate, with a great view of the Green Monster in left field and a sweeping view of the park. It’s a quirky, old-time park squeezed into a small urban box with odd angles and a cavernous centre field. The brick exterior and sheer history of the place only adds to the mystique.
I wasn’t feeling my best and couldn’t sample the lobster poutine with bacon and chowder or other culinary delights, but the chicken fingers were fine. Singing “Take Me Out to the Ballgame” with 35,000 new friends during the seventh inning stretch was fun, as was the traditional belting out of “Sweet Caroline” in the eighth inning.
Getting an Uber outside the park right after a game is a daunting task, so I’d suggest repairing to one of the local bars or restaurants and sipping a beer or a cocktail while you wait for the traffic to clear.
DAY THREE
AN ENTERTAINING SEAPORT TOUR
The Institute of Contemporary Art in Boston’s Seaport District. Jim Byers Photo
We had a fine morning tour of the booming Seaport District with Sam Jones, a local historian and a fine guide who works for the Boston History Company.
This was once a bustling center for fishing and fish processing at giant wharves, but sprouted into a new haven for high-tech companies and other businesses after the Boston Big Dig project buried a nearby expressway, which allowed the district to connect better to the city’s existing roads and helped open the are up for new development. The Ted Wiliams (there’s that name again) tunnel connects the Seaport District to nearby Logan Airport, which makes the area even attractive.
Jones showed us the gleaming Boston Convention Center, officially known as the Thomas M. Menino Convention & Exhibition Center, named after the city’s first Italian-American mayor. Menino had a funny way of talking and was often known by the nickname “Mumbles,” which I find delightful.
Jones also pointed out the Leaderbank Pavilion, with its white, sail-like appendage. It’s a popular spot for outdoor concerts.
A view of downtown Boston from the Seaport District. Jim Byers Photo
We also strolled past the Institute of Contemporay Art, a popular spot with an overhang that juts out over the harbor. Jones told us it’s used every year for the Red Bull diving competition.
As we walked along, Jones egaled us with stories about colourful Boston locals, including infamous mob boss Whitey Bolger. We also checked out the Moakley Center, a graceful, I.M. Pei design on the waterfront with a giant, curved facade. We also enjoyed the relaxed green space around Fan Pier Park.
If you walk past the delightful, crowded Barking Crab restaurant you can gaze across the water at the Boston Tea Party Museum, which explains the history of the insurrection, in which enraged colonists dumped barrels of tea into the ocean to protest British taxes.
A FABULOUS LUNCH
The lobster popover at Woods Hill Pier 4 restaurant in Boston. Jim Byers Photo
Woods Hill at Pier 4 is a tremendous spot for a meal. There are big windows looking out at the harbor and a nice patio, along with a bright, colourful painting along the wall near the bar. We had a lovely server and enjoyed a tremendous lobster popover, as well as a very good steak sandwich with melted Mexican cheese and onions on soft bread. They call it a Steak Patty Melt, which I find odd as a patty melt is a hamburger with cooked onions and American or Swiss cheese on toasted rye bread. Call it what you like, it was still tasty. Maybe even better were the excellent beignets with dulce de leche and peach butter.
On or way to Long Wharf for our Boston Harbor tour, we stopped at Dandelion Coffee on Rowes Wharf and enjoyed views of the Clock Tower and Grain Exchange buildings, two beautiful structures I didn’t remember from my previous visits to the city. We had a brief chat with a couple of women who were big Chicago Bears’ fans and enjoyed one of the creamiest coffee lattes I’ve ever sipped.
A GREAT HARBOR TOUR
Boston Harbor, with the USS Constitution and the Bunker Hill monument in the background. Jim Byers Photo
A one-hour tour of the busy Boston Harbor is a great way to learn about the area’s rich history and get your bearings in a town that owes its existence to the ocean. We enjoyed fine views of the Seaport District and Fort Independence from the water, and also planes coming into land at Logan Airport, which were only a few hundred feet overhead.
The harbor was filled with private power boats, sailboats, amphibious land and water boats, tiki boats for party types, and more. One of the more interesting sites for a Canadian was the tall ship Caledonia, which is a fine spot for drinks and a bite to eat and offers terrific sunset views of the city.
The Caledonia was a British-built fishing trawler that was built in 1947 and was named the Petrel when it sailed the waters of the Great Lakes (including, ahem, Lake Ontario). It was moved to Nova Scotia in 2001 and rebuilt as a barquentine, and then was sent south to Boston in 2019. Off in the distance we could see the Tobin Bridge, which is painted a soft shade of green called Monster Green; the same as the Green Monster left field wall in Fenway Park. Somehow I find that quite endearing
We also got a look from afar at the Bunker Hill monument, which celebrates the U.S. Revolutionary War battle of the same name. Down on the water you’ll find the iconic American ship The U.S.S. Constitution, which was built in 1797 and served in many a battle during the War of 1812. Nicknamed “Old Ironsides” because of her seemingly impenetrable hull (actually made of Georgia pine), the ship never lost a battle. She’s now the second oldest naval vessel still in commission in the U.S.
As we headed back to the dock, we could see the Old North Church and Faneuil Hall, which hosted many a Revolutionary War protest and meeting. Next door to Faneuil Hall is the popular Quincy Market, a 200-year-old market and food hall. Finally, our guide offered a nice tip for families; the New England Aquarium has an outdoor tank where you can admire sea lions and seals at no charge.
A SUBLIME GREEK TREAT
The food and decor are truly stunning at Kaia restaurant. Kaia Boston/Meet Boston Photo
This is a truly wondrous restaurant in the South End that serves up modern takes on Greek classics. The decor at Kaia is sexy and spectacular, like a touch of Santa Monica or Miami Beach, and the service is superb. Even the leather menu was cool. The menu (is focused on appetizers and fresh fish, with some meat specials. Each dish had a special flavour and something unique, and the presentation was excellent.
We started with an appetizer with an oyster, delicious hamachi and a tiny crab claw. The spanakopita?? Was light and fluffy with crispy edges, and the hamachi curd came with crunchy pistachio and yogurt and chilli oil. Divine. The crispy potatoes were creamy on the inside and we enjoyed a wonderful sea bass with orange blossom honey and spices, with a serving of olive oil, lemon and fresh herbs added in a table side ceremony.
We also dove into chicken gyro with moist but crispy chicken bits and blazing hot pita. The olive oil cake with orange, strawberry, yogurt gelato, and strawberry foam was fresh and delicious and not too heavy. They have a nice selection of Greek wines. All in all, an exquisite dining experience in a part of town I wasn’t familiar with.
A FINE HOTEL
Our view from room 801 at the Royal Sonesta Hotel, Boston. Jim Byers Photo
The Royal Sonesta Boston is an iconic AAA Four Diamond hotel situated along the Charles River where Cambridge meets Boston. It recently underwent a comprehensive transformation that gives it a welcoming and stylish feel. The river views (we were in room 801, a spectacular and spacious room I highly recommend) make you want to set the alarm for sunrise, and there’s tons of cool and inspiring art all around the hotel. There’s a large indoor pool with a soaring glass ceiling and an outdoor patio, as well as a nice, well-equipped fitness centre. There’s a casual restaurant called Scull and Keel, as well as the MonteVerdi restaurant for fine Italian dining, and a Starbucks. I’ll soon post a full hotel review in this space.
Getting There: Air Canada and Porter Airlines both fly to Boston from Toronto. The city is a five or six-hour drive from Montreal.
More Information: https://www.meetboston.com/
: A Fabulous and Fascinating City "Pin It")