CheckOut: Windsor Arms Hotel for Toronto Gay Pride (update)

By @ 05/16/19 in Gay pride, Gay travel, James Careless, ManAboutWorld, Toronto, Travel

Windsor Arms Hotel in Toronto for Pride and in ManAboutWorld gay travel magazineThis gorgeous Gatsby-themed 1927 small four-story hotel is a glistening gem in downtown (Bay and Bloor streets) Toronto. Just minutes away from the city’s Gay Village (Church and Wellesley), the uber-elegant Windsor Arms is a five-star hotel of just 28 suites; many of them having multiple rooms. (I stayed in a multi-room 700 square foot Deluxe Suite, which was worthy of Jay Gatsby.) The insides and outsides have been lovingly rebuilt and revived by new owner George Friedmann. Past prominent guests include Barbra Streisand and Elizabeth Taylor; you never know who you might see today! (Susan Sarandon and Ben Stiller were spotted here at a recent event.)


Given the Windsor Arms’ coterie of elegant suites, many fine restaurants and pampering facilities, and prime location (it is just off Windsor Arms Hotel in Toronto for Pride and in ManAboutWorld gay travel magazineBloor on the surprisingly quiet St. Thomas Street), prices here are not cheap. During this year’s Pride Toronto festival (it runs June 1 to July 1, 2019), nightly rates start at US$292 (excluding taxes and fees) and hit $1335 for the 1500 square foot Windsor King suite. But think about it: This suite comes with a king and a double sofa bed. Split between two couples, you and your friends could have a super-luxurious and exclusive stay for just $333.75 each. That’s a bargain price for a small historic hotel so charming and different, you will love it as much as Babs and Liz did. It is worth noting that the Windsor Arms does not nickel-and dime its guests. The Wi-Fi is free, the in-room Nespresso coffee is quality, and the towels/dressing robes full and fluffy. Meanwhile, the hotel has been serving afternoon tea without fail since it opened in 1927; offering with delectable sandwiches, scones and pasties – and more fine teas than you ever knew existed.


Given that is close to fashionable Yorkville, still sinful Yonge Street, and Toronto’s Gay Village – plus steps from the city’s subway lines – the Windsor Arms hotel could not be better situated for gays of all flavours and levels of daring. Want access to Toronto’s very best, most exclusive shopping? It’s here. Want to visit the Gay Village and sample everything from its edgy restaurants and clubs to steamy bathhouses and other no-longer-forbidden fruits? It’s just a short walk away eastwards on Bloor to Church Street, and then south to Wellesley and beyond. Frankly, if you are of a mind to get naughty during Pride Toronto, the Windsor Arms is a logical base of operations; given that is close to everything that counts.


As mentioned above, the Windsor Arms’ rooms are all individually and beautifully decorated/furnished. Many of the rooms come with their own musical instrument for guests to play, from pianos in the largest suites to guitars and Celtic harps in the smaller ones. The bathrooms are also well-appointed with high-quality fixtures. For instance, the entry level, 550 square foot Junior suite features cream-colored walls with wooden accents (, residence-quality furniture, deep soaker tub, separate standing shower, and an acoustic guitar (which is regularly tuned). Like the high-priced suites, it also comes with ‘Butler Service’. This is a separate, lockable compartment beside the front door when food, towels, and other amenities can be discreetly delivered to without you having to interact with staff. Very useful if you are in the midst of naked passion and champagne suddenly arrives!

Gay Factor

Okay, so we’re talking about a very small, exclusive hotel in the heart of Toronto close to the Gay Village, with top-end decor, furnishings, amenities, food, drinks, and high tea; plus an indoor pool with fireplace and two floors of spa facilities? Plus Babs and Liz stayed here, and their photos adorn the walls. I mean, if you don’t get the gay factor here, I can’t help you. This is a perfect place for any gay or other LGBT couple, in a hotel with a reputation for welcoming gay guests with open arms. In fact, the only complaint I could find from a gay couple was that it was difficult to leave the Windsor Arms, because it is such a wonderful place to stay. (Friedman told me of one guest who called before arrival to ask for a bathtub full of Jello. The Windsor Arms’ only question to this request was to ask the guest, “what flavour?”)

About the CheckOut

ManAboutWorld highlights properties we have recently and personally stayed at, and is editorial, not advertorial. Like virtually all travel publications, we sometimes accept discounted and sponsored travel, but ManAboutWorld is beholden to no one but you. Our recommendations are based solely on the experience and opinions of our editorial team and trusted network, putting our readers’ interests above all. If you ever have an issue with anything we recommend, please let us know. We always have your back, and your travel satisfaction in mind. Read our full disclosure here.

This post originally appeared in 2016 and has been updated today by the original author, James Careless, based on a recent visit.


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