Entrepreneur, Foodie Explorer
Adventurists.CA runs amazing FREE walking tours in the city of Toronto. I would start my morning with them and learn some really cool stuff about the history of Toronto and it's secret places. The guides are super knowledgeable and friendly too!
All that walking is going to work up an appetite! I recommend SCHOOL restaurant in Liberty Village for a late brunch. The food is mindblowingly delicious and the cocktails are great too. Save room for dessert from the in house bakery. My fave dish is the fried chicken and waffles with tobasco honey.
Relax after that delicious meal in Trinity Bellwoods. Bring something to read, or a frisbee and enjoy some afternoon sun before the evening festivities.
Start the evening with a self guided cocktail crawl down Ossington (between Queen St and Dundas St) I love the margaritas at Fish Bar, the Fresh Material at Hawker Bar, and the Langkawi at Soos. Reposado has a great vibe for Tequila lovers too!
What better way to end the day then from the top of the CN tower gazing out over the beautiful city of Toronto. The food here is excellent and dinner includes access to the glass bottom observation deck. Not to be missed!
I would stay at the Drake Hotel. Super fun and trendy - they have an excellent rooftop patio and a great bar! Makes getting home at the end the night easy peasy!