Since you arrive today and it's already midday in Toronto, start with a relaxed brunch at School, a roomy spot near Queen West known for shareable boards and great coffee, then walk off the meal with a stroll through Trinity Bellwoods Park to stretch legs and enjoy local life. If anyone needs groceries or last-minute supplies for the Airbnb, pop into St. Andrew Market or the nearby Loblaws CityMarket to stock up before checking in and settling everyone into the rental.
After brunch and a park stroll, head to Kensington Market to wander its colorful lanes, vintage shops, and mural-filled courtyards-pick up unique snacks and people-watch at a sidewalk cafe. Later, make a relaxed stop at Graffiti Alley for quick photos, then grab early evening bites and local craft beers on the lively patios of Ossington Avenue before returning to the Airbnb to finish settling in.
As twilight falls, take the group for dinner at the lively rooftop patio of The Broadview Hotel's Rooftop for panoramic skyline views and shareable plates, then wander down to Distillery District for a post-dinner stroll among cobblestone lanes, art galleries and boutique shops lit up at night. Cap the evening with cocktails and dancing at Rebel (a short ride away) or a more laid-back brewery vibe at Bellwoods Brewery to suit the group's energy before heading back to the Airbnb to unwind.
Start the day with breakfast at FBI Foods & Deli or grab pastries and coffee to-go from Sam James Coffee Bar before heading toward the lakeshore; stroll along the scenic Waterfront Trail to soak in morning views and public art installations. From there, hop on the short ferry or walk to Toronto Islands for a relaxed bike ride or picnic at Centre Island and panoramic city views-return mid-morning to explore the waterfront parks and pop into the interactive exhibits at Harbourfront Centre before lunch.
After returning from the islands, head inland to climb the iconic CN Tower - opt for the EdgeWalk or the glass-floor LookOut level for adrenaline and unbeatable city views - then descend to explore the interactive exhibits and shark tunnels at [Ripley's Aquarium of Canada](https://www.ripleyaquariums.com/canada/) for a close-up marine experience. Finish the afternoon with waterfront cocktails and small plates at Amsterdam BrewHouse on Queens Quay, where the patio overlooks Lake Ontario and sets a relaxed mood before an evening in the Entertainment District.
After a day on the waterfront and at the tower, head to King Street West for dinner at Bymark or the lively small-plates scene on King West (great for groups), then wander to The Rec Room at Roundhouse Park for arcade games, live entertainment and craft cocktails-perfect for a big group vibe. Finish with late-night live music and dancing in the Entertainment District at The Citizens or catch a DJ set at Toybox to keep the party rolling before returning to the Airbnb.
Begin with a hands-on breakfast at Good Egg for elevated comfort dishes, then wander the bohemian lanes of Kensington Market, popping into vintage shops, spice stalls and the vibrant murals; grab a street-food snack (try a Jamaican pattie or empanada) to sample as you explore. Mid-morning, head east to The Power Plant Contemporary Art Gallery at the waterfront for a quick modern art fix, then stroll through [Allan Gardens Conservatory](https://www.toronto.ca/explore-enjoy/parks-gardens-centres/allan-gardens-conservatory/) to warm up among tropical plants before the afternoon's museum crawl.
Head to St. Lawrence Market for a lively tasting tour-sample peameal bacon sandwiches, artisanal cheeses and fresh bakery treats while browsing specialty stalls, then take a short walk to the nearby [Saint James Cathedral](https://www.stjamescathedral.ca/) to admire its stained glass and quiet cloister. From there, dive into culture at the [Royal Ontario Museum (ROM)](https://www.rom.on.ca/en)-focus on the dramatic dinosaur halls and the James and Louise Temerty Galleries of the Age of Pandemics and global cultures-then relax with late-afternoon coffee and people-watching on the terrace at Museum Tavern before the evening program.
Wind down tonight with a cozy, chef-driven dinner at Patois, where inventive Caribbean-Asian dishes and shareable plates make it easy for a group to sample and compare. After dinner, stroll through the nearby lantern-lit paths of Allan Gardens Night Walks (check seasonal hours) or head for craft cocktails and a relaxed lounge vibe at Bar Isabel to compare tapas-style bites and end the night with easy conversation before returning to the Airbnb.
Ease into the day with brunch at Dineen Coffee Co. followed by a guided mural walk through the nearby West Queen West arts corridor to admire street art and boutique galleries. Mid-morning, explore the independent shops and artisan studios in the Junction Triangle, grab specialty pastries at Rooster Coffee House, and pop into Elsewhere Records for vinyl hunting before regrouping back at the Airbnb to prep for the evening.
Spend a leisurely afternoon wandering the cobbled lanes of the Distillery Historic District, popping into galleries at Gooderham & Worts and sampling artisanal chocolate at SOMA Chocolatemaker, then join a guided craft-beer or spirits tasting at Spirit of York Distillery to learn local methods and sip small-batch spirits. Afterward, cross to nearby Cherry Street Wharf for waterfront photos and light bites at The Broadview's café outpost (or another seasonal patio), letting the group relax before heading back to King West to dress up for the night's festivities.
As night falls, dine family-style on wood-fired fare and shareable plates at Kingston Social (great for groups) before heading to Cluny Bistro for late-night cocktails in an atmospheric Parisian-inspired setting. After drinks, dive into King West's club scene with bottle service and a DJ at Lavelle or catch an energetic live set at Good Behaviour to keep the group dancing until late.