How to blend work with play in Toronto this winter

The Kimpton Saint George is ideally located for business and leisure

The Kimpton Saint George is ideally located for business and leisure
Photo: Francisco Sanchez

After a busy day of work in Toronto, a friend and I sat by a glowing fireplace, sipping red wine and savouring slices of artisanal pizza, while a charcuterie tray piled with fine cheeses and an array of drinks lay within easy reach.

It felt less like a business trip and more like a cozy evening at home with friends yet this was actually Social Hour at the Kimpton Saint George, an inviting daily ritual, complimentary for hotel guests from 5 to 6 p.m. Other hotel guests arrived with a mix of energy, some fresh from a leisurely ride on the hotel’s complimentary bikes, others unwinding after a day packed with meetings or client calls. The atmosphere struck the perfect balance between relaxation and productivity, reminding me how seamlessly business and leisure can blend in Toronto.

Whether you’re sealing deals by day or indulging in dining and entertainment by night, Toronto offers the perfect backdrop for blending work with play.

Refined Living at the Kimpton Saint George

The Kimpton Saint George, my home for a three-day stay in Toronto, was the ideal base for balancing work and exploration. The 14-story, 188-room boutique hotel offers 20 suites, a Presidential Suite, and well-designed, ground-level meeting spaces.

The Kimpton Saint George in Toronto

The Kimpton Saint George features residentially-inspired design
Photo: Kimpton Saint George

From my guest room on the 11th floor, I had fabulous skyline views of the neighbourhood’s mix of old and new architecture. A Gothic-style church with copper spires stood among mid-century residential and office buildings, while the tree-lined urban streets below bustled with pedestrians and cyclists.

Known for its residentially-inspired design, the Kimpton Saint George’s decor is understated yet thoughtful, with a mix of textures and natural materials like stone and leather complementing the contemporary furnishings. The space felt elegant but comfortable.

Cotton bathrobes, slippers, rain shower, luxury bath amenities, king-size bed and complimentary yoga mat made for a restful sanctuary at day’s end. With the Kimpton Plant Pals Program, guests can even request a plant to further enhance their stay.

Neighbourhood Attractions

Casual dining at Eataly Yorkville 

Casual dining at Eataly Yorkville 
Photo: Francisco Sanchez

Stepping outside the Kimpton Saint George, the neighbourhood itself is part of the experience. Located on Bloor Street in the Annex, the hotel is surrounded by the University of Toronto’s campus and quiet residential streets lined with red brick homes featuring Romanesque arches and Queen Anne-style turrets.

Just steps away are independent shops, cafes, and pubs, along with major attractions such as the Gardiner Museum and the Bata Shoe Museum, while historic Casa Loma is a 30-minute stroll north.

Market fresh fare at Eataly Yorkville

Market fresh fare at Eataly Yorkville 
Photo: Francisco Sanchez

Across Bloor, the striking crystal-shaped addition to the Royal Ontario Museum, designed by Daniel Libeskind, marks the entrance to Yorkville’s “Mink Mile” where pedestrian-friendly pathways connect high-end boutiques, fine dining and art galleries.

One of my first stops was Eataly Yorkville, where ALPINA, a limited-time pop-up running through March 2025, recreates the après-ski atmosphere of a baita (mountain retreat) in the Italian Alps. The immersive experience includes themed events, workshops, Happy Hour specials, and hearty Alpine cuisine, from a polenta bar with savoury toppings to Italian-style fondue and truffle butter gnocchi.

Waterworks Food Hall

It’s a short walk to the hip and happening Waterworks Food Hall
Photo: Francisco Sanchez

Another memorable culinary stop during my Toronto stay was Waterworks Food Hall in Richmond Street West, housed on a site that once served as St. Andrew’s Market, a commercial hub dating to 1837. Originally the public market provided fresh produce, meat, and fish to the growing city. It was demolished in 1931 and replaced by the Art Deco Water Works Building, which remained in operation until 2013.

Modeled after European food halls, today, the historic landmark space blends restored architecture with a dynamic marketplace featuring 40 indie vendors offering specialty fare to go. Among the diverse food and beverage stalls, international cuisines include Soi Thaifoon, Taco Lupita, and Karak, known for its inventive Pakistani fusion dishes.

The open design, featuring skylights streaming in sunlight, floor to ceiling windows and communal seating in the Great Hall, makes it an atmospheric spot to gather in every season.

Evening Diversions

Equally worth exploring, especially at nightfall, is the food hall at The Well, an upscale  lifestyle complex in the Fashion District. Its lively common areas host after-work cocktails, casual meals from 50 licensed vendors at Wellington Market, and an evolving lineup of DJs, art performances, and pop-up events. While there, I came across a Nordic-inspired hut with lounge chairs and fire pits—a perfect spot to unwind under a warm throw.

Roy Thomson Hall in Toronto

Catch a concert at Roy Thomson Hall 
Photo: Francisco Sanchez

For a change of pace, you can also take an evening off to catch a live performance at one of the Mirvish theatres. From Broadway hits to original Canadian productions, Mirvish brings world-class theatre to Toronto across its four venues, including the Royal Alexandra Theatre and the Princess of Wales Theatre. Whether it’s a high-energy musical or a thought-provoking play, it’s a great way to experience the city’s performing arts scene.

For music lovers, a highlight of the 2025/2026 season (and running through March 15th), the musical Just For One Day revisits the historic 1985 Live Aid concert that featured Queen, David Bowie, Elton John, and Tina Turner among others and was organized by Bob Geldof and Midge Ure to raise funds for famine relief in Ethiopia.

Whether you’re in town for a weekend or balancing business with leisure, there’s no shortage of places to explore and plenty of ways to make the most of your stay in Toronto.

Travel Planner

Kimpton Saint George: 280 Bloor St W, Toronto www.kimptonsaintgeorge.com

Eataly Yorkville: www.eataly.ca/stores/eataly-yorkville/

Gardiner Museum: www.gardinermuseum.on.ca

Royal Ontario Museum: www.rom.on.ca

The Well: thewelltoronto.com

Waterworks Food Hall: www.waterworksfoodhall.com

Destination Toronto: www.destinationtoronto.com

Michele Peterson is an award-winning travel writer who specializes in food, drink and sun destinations. Her work has appeared in major magazines, guidebooks and travel anthologies. Get recipes, travel tips and inspiration on her A Taste for Travel blog or via Twitter/Instagram @atastefortravel   

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