Whether it’s in time for Mother’s Day or you’re planning something special for a milestone birthday later this year, a multigenerational weekend getaway in Toronto is the perfect way to celebrate two, three or even four generations of love.
We’ve planted multigenerational memories in my family’s digital scrapbook for years, including a four-generation photo shoot while my last remaining grandmother was still alive, and taken mother-daughter trips for years, like my visit with Miss Q to northern Ontario last summer that inspired this Things to do in Sudbury post.
My advice? Don’t wait for life to sort itself out — proactively create the moments you will cherish one day. You will never regret curating memories.
If you’re already going to be in the GTA or want to plan a multigenerational weekend getaway in Toronto, here’s a 24-hour plan so even one night away together feels like a true escape.
Your multigenerational weekend getaway in Toronto starts here…
You’re going to need a home base for your weekend getaway in Toronto, and since this is a multigenerational affair, you’ll probably want beds for everyone and some space to relax and enjoy each other’s company during downtime (not that this itinerary is going to give you too much of that!). Toronto’s Chelsea Hotel is the perfect spot.
Centrally located at Gerrard and Yonge Streets, the Chelsea is only a block or two from the Eaton Centre, minutes on foot to Nathan Phillips Square and Queen St. W. shopping, and an easy subway ride to the CN Tower and Ripley’s Aquarium if you decide to stay longer than this one-night itinerary.
And with more rooms than any other hotel in Canada, there’s definitely a room configuration that’ll work for your weekend getaway in Toronto. For us — my Mom, my daughter and me — a double-queen room with an adjoining parlour room did the trick. The add-on parlour room provided a separate living space with a sofa that turned into a bed at night for Miss Q, while my Mom and I each scored a comfy queen bed.
The Chelsea has had a major renovation underway for a few years now, so many of the rooms have been totally overhauled and updated. We’ve stayed in the “blue elevators” bank of rooms before and they’re always lovely. They’re spacious, too, so you’re not climbing over luggage to get to your bed or the washroom.
A 24-hour itinerary for your multigenerational escape
Obviously, you can rearrange this in any order that works for you, shifting things as needed based on your arrival time, show tickets, etc. And you can (and should) also add on a second night if you’re visiting from farther away. But you’re also welcome to recreate a carbon copy of our multigenerational weekend getaway in Toronto; after all, I’ve already done the work for you, so make it easy on yourself!
DAY 1
Morning: drive, train or fly to Toronto.
11 a.m.: soft check-in at the Chelsea Hotel. Drop bags with bellman for secure storage while you go out and about.
11:15 a.m.: shopping! There are so many options nearby, depending on your mood. For deal-hunters, there’s an amazing WINNERS at College Park (444 Yonge St.), though you may want to pop in to the Aura Skyscraper (384 Yonge St.) on your way from the Chelsea, where you’ll find both a Marshall’s and a really great IKEA that’s got an awesome café inside where you can grab a light lunch or snack to keep you fuelled until dinner. We paid $8.88 to share a hot dog, super-fresh egg salad sandwich and a couple of juices; you’d be hard-pressed to find a more economical option anywhere in downtown Toronto. If you’re moving at a pretty good clip, you’ll probably have time to pop into the Eaton Centre (220 Yonge St.) as well.
3:30 p.m.: head back to the Chelsea Hotel for check-in. Consider changing into swimsuits to do the corkscrew waterslide, but call the front desk to see what time it opens first. We were there on a Friday and it didn’t open until 4 p.m., which sadly didn’t work with our dinner plans. It’s really cool because it goes right out of the building before it weaves its way back in, and multigenerational fun is guaranteed, so check it out if the timing works.
4:45 p.m.: enjoy a pre-show dinner at the Elm Street Bar & Lounge. You can enter from the Chelsea’s lobby so you don’t even need to bring a coat if you have no plans to do anything but veg in your room after dinner. The menu doesn’t change often but the food here is consistently very good — with huge portions. Plus, there’s a kid’s menu with fan favourites for the younger set. My personal recos include the root vegetable and chèvre salad, heirloom tomato and burrata salad, gochujang chicken wings, cranberry & candied pecan baked brie, tomahawk pork chop, butter chicken and the seafood tortelli. Finish it all off with the very yummy carrot and almond cake (you won’t be sorry that you indulged, trust me).
6:30 p.m.: if you can plan your weekend getaway in Toronto around a play, concert or musical, the symphony or ballet, you’ll be unlocking some of the best the city has to offer. We have world-class performances here nearly every day of the week and it would be a shame not to build one of them into your itinerary. As big ABBA fans, the three of us decided to have our multigenerational escape coincide with a Candlelight Concert.
I’d been to one before, featuring Adele’s music — during a weekend in Toronto for a girlfriend getaway, which also has a tonne of ideas you could add to this itinerary — and absolutely loved it, so I knew my mom and daughter would love hearing ABBA performed by a string quartet — and I was right. The hour-long performance is just the right length after a big meal and the venue (Metropolitan Community Church, 115 Simpson Ave.) is almost a straight shot east on Gerrard St. from the Chelsea, making it an easy trek on public transportation and an even easier taxi or UBER ride.
8 p.m.: it’s been a big day and at least part of your multigenerational group is probably ready to unwind and go to sleep. The more energetic set may want to grab a nearby cocktail or hit up a private karaoke bar like Bar+Karaoke Lounge (360 Yonge St.) — a mere one-minute walk from the Chelsea Hotel.
DAY 2
7 a.m.: breakfast! Stay onsite and enjoy the convenience of the Elm Street Bar & Lounge again (the avocado toast and stuffed French toast are both amazing) or visit a Toronto staple like nearby Fran’s (20 College St.) if you want classic diner food.
8:15 a.m.: check out of the Chelsea if this is a one-night getaway. Store your bags with the bellman again or pop them down to your vehicle if you drove.
8:30 a.m.: head out the Chelsea Hotel lobby’s Elm Street exit and walk less than two minutes to the Elmwood Spa (18 Elm St.). Don’t forget your bathing suit, but no need to bring flip flops or a towel because you’ll be handed both once you reach the change room.
Housed in a building erected in 1890 that became the first YWCA in Toronto in 1930, the Elmwood Spa has evolved over the years but remains one of the most calming spaces in the city. It’s the ideal setting for a multigenerational weekend getaway in Toronto since it’s one of the few spas that allows children to join their mothers and grandmothers not only for services but also water therapies and onsite meals. It was so special to share a day spa experience among three generations of my family even though Miss Q is only 14.
Even if you only book a single service (valued at $150 or more), you have complimentary access to the spa’s water therapies, which includes a woman-only hot tub located inside the women’s change area plus co-ed spaces like a body-temperature pool, hot tub and steam room. This turns your spa service into a spa experience!
And if you’re reading this in time for Mother’s Day, the Elmwood Spa has two special packages available:
- Polished Perfection (5 hours, $343 per person [valued at $385]; taxes/gratuities extra) — Water Therapies, 3-Course Lunch, Essential Manicure, Essential Pedicure and 50-Minute Swedish Massage.
- Precious Moments (4 hours, $370 per person [valued at $420]; taxes/gratuities extra) — Water Therapies, 3-Course Lunch, 50-Minute Swedish Massage and Skin Regimen LX Longevity Vitaminic Facial.
I looooooved the Precious Moments package and upgraded the Swedish massage to a deep-tissue massage, which was pure heaven. The Elmwood’s new facial treatment — the Skin Regimen LX Longevity Vitaminic Facial — features a high dose of Vitamin C with a pink clay treatment and something called Longevity Complex™. My aesthetician used advanced skin-stretching and massage techniques to revitalize and plump up my facial tissue and deliver an anti-gravity effect. If you’ve ever had a facial with this kind of lifting power, you know that you really can see a before-and-after difference. It’s an excellent facial. Treat yo’self.
Since our packages included lunch, we stayed onsite to eat in our bathrobes, which is one of my favourite things to do when I want to feel super-bougie.
Afternoon: if you’re not staying for lunch at the Elmwood Spa, hit up one of Toronto’s many fantastic restaurants. Close to both the Chelsea Hotel and spa, there are some great choices for every budget, such as Richmond Station, Trattoria Mercatto and Cafe Landwer. And if you don’t need to zip home just yet and didn’t get your fill of shopping, there’s a great stretch of shops all along Queen Street West and on Ossington, with more restaurants to choose from on both.
It doesn’t matter how you decide to structure your multigenerational weekend getaway in Toronto, just DO IT. Book the hotel. Eat the cake. Make the memories. You’ll thank me for it later.
DISCLAIMER: The Chelsea Hotel sponsored this weekend getaway in Toronto content; my opinions and recommendations remain entirely my own.
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