Dark Feminine Travel Guide: A Long Weekend in Toronto
Where to stay, wander and misbehave for three days in the city
By: The Lace Ledger Staff
Toronto is so much more than Blue Jays games and Steam Whistle beneath the CN Tower. Look beyond the postcard version and you’ll find Gothic architecture rising among storied institutions, all set against a creative culture that rewards a little curiosity. For a long weekend worthy of your darker inclinations, we’ve curated a lux itinerary that sways between the city’s gothic heritage and its more decadent pleasures. There will be art and fashion, with a few wonderfully strange discoveries waiting along the way.
FRIDAY: SOFT LANDING
Travel days ask enough of you. Friday night is designed to shake off the airport and settle into the city without demanding too much. Start by disappearing into thermal waters, then let dinner inside a Victorian mansion offer a taste of what’s ahead before one last drink sends you upstairs for the night.
4:00 P.M. — CHECK IN: THE DRAKE HOTEL
1150 Queen St. W., Toronto, ON M6J 1J3
Photo Credit: thedrake.ca
Make West Queen West home for the weekend at The Drake, Toronto's art-filled boutique hotel and a fixture of the neighbourhood for more than 20 years. Its 51 individually styled rooms span two wings; for a little extra character, book the Classic Wing in the original heritage building, steps from the hotel's Lounge, rooftop and underground music venue.
5:00 P.M. — RECENTRE: AIRE ANCIENT BATHS
510A Front St. W., Toronto, ON
Photo Credit: Aire Ancient Baths
Wash off the flight with a circuit through eight thermal baths, a steam room and dry sauna inside AIRE's atmospheric 23,000-square-foot space. The setting is part of the appeal: the baths occupy a restored 1912 Edwardian Classicism building that once housed the Copp Clark publishing company, bringing a little Toronto history to your first few hours in town.
9:00 P.M. — DINNER + DRINKS: STORM CROW MANOR
580 Church St., Toronto, ON M4Y 2E5
Photo Credit: Storm Crow Manor
Ease into Toronto's stranger side over dinner and cocktails inside a historic three-storey Victorian mansion in the Church-Wellesley Village. Storm Crow's eight fantastical rooms include the Mary Shelley Bar, an alternate-reality Victorian hunting lodge, Heaven, Hell and a Shining-inspired Red Rum Room, while bubbling cocktails and roll-of-the-dice menu options keep the first night deliberately unserious.
11:00 P.M. — NIGHTCAP: THE DRAKE LOBBY BAR
1150 Queen St. W., Toronto, ON M6J 1J3
Photo Credit: thedrake.ca
Come back to Queen West for one final drink downstairs at The Drake. Depending on the night, linger in the Lounge, head up to the Sky Yard or follow the music underground—then enjoy the greatest luxury of staying where you sip: your bed is upstairs.
SATURDAY: INDULGENCE
Saturday belongs to wandering the West End. Spend the day hunting through designer resale and lingerie shops, dipping into horror and oddities whenever curiosity intervenes. By evening, trade the shopping bags for wild Canadian fare before dressing up for high culture; theatrical cocktails follow, with a little low culture waiting for anyone whose stamina survives.
FROM 10:00 A.M. — EXPLORE THE WEST END
Give yourself the afternoon to explore. These five TLL-approved stops make a loose loop through some of the West End's most interesting neighbourhoods, with plenty of opportunity to stop when something else catches your eye along the way.
VSP Consignment
1410 Dundas St. W., Toronto, ON
Start with the hunt: VSP's designer consignment spans contemporary ready-to-wear, shoes, bags and accessories, making it a very good place to find the souvenir you absolutely did not budget for.Gigi's House of Frills
731 Dovercourt Rd., Toronto, ON
Make the pilgrimage North for lingerie at Gigi's, an independent boutique where labels like Dita Von Teese and What Katie Did share the racks with Playful Promises. Vintage treasures turn up among the new arrivals, with hosiery and pieces from local designers extending the hunt.Curiosa
320 Harbord St., Toronto, ON
Head East for a little magic. Inspired by historic cabinets of curiosity, Curiosa is packed with fantastical books, jewellery, stationery, candles, unusual gifts and objects that seem designed specifically to follow you home.Little Ghosts Books
930 Dundas St. W., Toronto, ON
Turn back toward Dundas for Canada's first horror-focused bookstore, an independent shop dedicated to horror, paranormal and dark fiction from major publishers and small presses alike. There's a café inside, making this your strategically placed mid-afternoon coffee stop.SkullStore Oddity Shop & Prehistoria Museum
1106 Queen St. W., Toronto, ON
Finish back on Queen West among skulls, fossils, taxidermy, natural-history specimens and other curiosities at SkullStore. Its accompanying Prehistoria Museum makes this as much an attraction as a shopping stop—check its current exhibition status before visiting as the museum settles into its new Queen West home.
4:30 P.M. — RESET: THE DRAKE HOTEL
1150 Queen St. W., Toronto, ON M6J 1J3
Drop the bags, put your feet up and refresh for the evening. You've earned an hour horizontal!
6:00 — DINE: ANTLER KITCHEN & BAR
1454 Dundas St. W.
Chef Michael Hunter’s intimate dining room celebrates Canadian ingredients through an ever-changing menu where wild game meets locally foraged ingredients, all guided by the bounty of all four seasons. When you love it as much as we do, pick up The Hunter Chef Cookbook to recreate some of his delicious creations at home.
8:00 — CHECK THE MARQUEE
Ballet / Opera / Burlesque
Toronto knows how to put on a performance, so leave Saturday night partly to chance. Check what’s on during your stay at the National Ballet of Canada and Canadian Opera Company, or look to the city’s independent stages and burlesque performers for something a little more provocative.
AFTER THE CURTAIN — BARCHEF
472 Queen St. W.
Put that snazzy outfit to good use after the show and head to BarChef, where cocktails are treated with the ceremony and imagination of a tasting menu. Unexpected ingredients arrive in elaborate presentations, producing drinks dramatic enough to qualify as the evening’s encore.
STILL AWAKE? — SWAN DIVE
1631 Dundas St. W.
Photo Credit: Scoundrels Field Guide
Trade the theatre seats for a bar stool at Swan Dive, a beloved Dundas West dive where the pool is free and the pinball machines give the room almost as much personality as its regulars. It’s casual, a little scruffy and exactly the right place to let an otherwise polished evening come slightly undone.
SUNDAY: OLD MONEY
Sunday heads uptown for a grander side of Toronto. The day moves from castle halls to fashion history before slowing down over afternoon tea, then closes with sunset views and a few locals who never quite left it.
10:00 A.M. — EXPLORE: CASA LOMA
1 Austin Terrace, Toronto, ON M5R 1X8
Photo Credit: Casa Loma
Start early at Toronto’s very own castle, the Gothic Revival mansion financier Sir Henry Pellatt completed in 1914. Wander its grand rooms, towers, gardens and underground tunnel before the day gets busy—and keep an eye out for the darker stories that have accumulated around the property over the past century.
12:00 P.M. — COVET: BATA SHOE MUSEUM
327 Bloor St. W., Toronto, ON M5S 1W7
Photo Credit: Bata Shoe Museum
Follow centuries of fashion history through a collection of nearly 15,000 shoes and related objects spanning cultures, continents and some 4,500 years. General admission is currently free on Sundays, leaving a little more in the budget for the vintage shopping you did yesterday.
2:30 P.M. — HIGH TEA: WINDSOR ARMS HOTEL
18 St. Thomas St., Toronto, ON M5S 3E7
Photo Credit: Windsor Arms Hotel
Dress accordingly. The Windsor Arms has been serving afternoon tea since 1927, pairing finger sandwiches, scones, petits fours and pots of tea with the old-world surroundings of one of Yorkville’s most storied boutique hotels. Didn't bring a fascinator for the occasion? You can’t rent on-site ;).
6:30 P.M. — SUNSET: WRITERS ROOM BAR
4 Avenue Rd., Toronto, ON M5R 2E8
Photo Credit: Park Hyatt
Take a seat high above the city at the Park Hyatt’s Writers Room, a cocktail bar named for the literary crowd that once gathered at the hotel. Come around sunset to watch the skyline change by the minute over cocktails and something light to eat before the evening takes a supernatural turn.
8:30 P.M. — MEET THE LOCALS: GHOST WALK
End the night with the stories hiding behind some of Toronto’s stateliest façades. Check the calendar for a ghost walk through the University of Toronto, Yorkville or Queen’s Park area, where Gothic architecture provides an appropriately atmospheric backdrop to the neighbourhood’s history and reported hauntings.
MONDAY: ONE FOR THE ROAD
There’s no reason to leave a long weekend feeling depleted. Sleep in and check out at your leisure; the sightseeing is finished. Monday is reserved for one last low-key morning before heading home.
LATER MORNING — CAFFEINATE: CAFE23
728 Queen St. W., Toronto, ON M6J 1E8
Take one last stroll down Queen West for coffee and a light breakfast at this charming neighbourhood café. If the weather cooperates, find a seat on the hidden garden patio out back and enjoy a slower start to your travels home.
AFTERNOON — FLY HOME
Good hair, full camera roll. Toronto, we’ll be back.
Toronto’s history and culture could fill far more than a long weekend. Every neighbourhood reveals another chapter, shaped by the people who built the city and the creative communities continuing to reinvent it today. Better still, this itinerary doesn’t depend on patio season or peak summer weather; these are places worth discovering year-round, giving you an excellent excuse to return and see what else Toronto has been hiding ;).
Which activity are you most excited to try?
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