Curator’s statement
Toronto was the perfect backdrop for my first girls’ trip with a friend I hadn’t yet traveled with. You never quite know how you’ll mesh as travel companions until you’re sharing meals, wandering a new city, and finding your rhythm—but Toronto made it effortless. With incredible food, walkable neighborhoods, and endless little moments of delight, it’s a destination that rewards both chatter-filled afternoons and long stretches of peaceful, companionable quiet. This chic and slow-paced itinerary is designed for girlfriends or solo travelers who want to savor the city without the rush.
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Day 1: Brunch, markets & comedy night
The pancakes at Mildred’s Temple Kitchen
Ease into Toronto with a leisurely brunch at Mildred’s Temple Kitchen, the kind of bright, modern spot that sets the tone for a girls’ trip: warm, delicious, and just a bit indulgent (the pancakes are non-negotiable). From here, make your way to the Distillery District, a pedestrian-only historic neighborhood full of small boutiques, indie shops, and Canadian-made treasures. It’s an easy way to get oriented while wandering with a coffee in hand.
In the evening, enjoy an early dinner nearby before heading to an 8 pm show at Second City. Toronto’s comedy institution is sharp, quick, and reliably hilarious—the perfect way to kick off your weekend with shared laughter.
Day 2: Casa Loma, local bites & nightcaps
Daytime castle wanderings at Casa Loma
Start your morning with a visit to Casa Loma, Toronto’s iconic hilltop castle. Go during the day to explore the sweeping staircases, gardens, and secret passages—it feels like walking through a storybook, and the views of the city skyline are worth the climb.
Afterwards, fuel up at Schmaltz Appetizing, a classic Jewish deli with standout bagel sandwiches and smoked fish. This is the perfect casual lunch before slowing your pace for the afternoon—browse nearby shops, wander Queen West, or simply return to the hotel for a rest.
In the evening, head to the 1 Hotel Toronto lobby bar for cocktails and snacks. It’s lively, chic, and buzzing at night—the kind of place where you can people-watch for hours or settle in for a long, easy conversation.
Day 3: St. Lawrence Market & leisurely exploring
A perfect slow morning at St. Lawrence Market
Your final morning is all about Toronto’s world-famous St. Lawrence Market. Arrive hungry—this historic market is overflowing with local vendors, artisanal bites, produce, pastries, and everything in between. Grab breakfast on the go and explore at your own pace.
After the market, spend the remainder of your day doing whatever feels good: walking the waterfront, popping into small galleries, or having a long lunch before you head home. Toronto is a city best enjoyed without a tight schedule, so leave space to enjoy its easygoing rhythm.
Need to know
Toronto is incredibly walkable, though Ubers are plentiful and convenient at night. The city feels very safe, especially in the areas you’ll be frequenting on this itinerary. Toronto is a year-round destination, but weather shifts quickly—winter is cold, and spring can be rainy, so pack layers. If you’re traveling solo, this itinerary is especially comfortable and approachable.
Travel Advisor
Joanna Vinick
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