Looking for the perfect holiday accommodation at in the vibrant heart of Toronto? Whether you're seeking a lively weekend surrounded by exciting activities and things to do or simply want the best places to stay in this iconic Canadian city, Old Toronto offers a fantastic array of options for every type of traveler. As a single female adventurer who loves to keep active, explore fun and flirty venues, and indulge in memorable local experiences, you're in for an unforgettable weekend. This guide highlights the top 10 things to do in Old Toronto, Ontario, perfect for your upcoming getaway.
1. Explore the Historic Distillery District
Your adventure kicks off in the famed Distillery District, renowned for its beautifully preserved Victorian-era architecture, bustling craft boutiques, art galleries, and unique eateries. For an active morning, join a guided walking tour that delves into Toronto’s rich history while stopping at local cafes and shops. The vibrant street art and sprawling courtyards make it a great place for fashion-forward photos and lively conversations with fellow travelers. For a more immersive experience, check out their evening local experiences, including wine tastings and craft beer samplings. Discover the Distillery District.
2. Enjoy a Canadian Broadway Show or Live Music
If entertainment is your style, staying in one of the downtown vacation rentals allows effortless access to Toronto’s dynamic arts scene. Book tickets to catch a holiday show or a live concert at renowned venues like the Royal Alexandra Theatre or Toronto Music Garden. These places to stay in locations near the entertainment district make it easy to hop from your short term rental to world-class performances. There's nothing like combining your love for arts with a flair for fun and flirtation. For upcoming shows and tickets, visit Theatre Toronto.
3. Wander Through St. Lawrence Market
For the foodie and active explorer, a visit to St. Lawrence Market is a must. This historic marketplace is packed with vendors offering everything from gourmet cheeses and fresh produce to artisanal baked goods and international delicacies. Grab a delicious breakfast and then explore the surrounding places to stay in the Old Town area. It's perfect for a active morning stroll and sampling the city's diverse flavors, making it a superb activities choice for singles who appreciate both culture and cuisine. Make sure to check out their local experiences events about Toronto’s culinary scene.
4. Take a Ferry to the Toronto Islands
One of Toronto's best-kept secrets is the magnificent Toronto Islands. Hop on a ferry from Jack Layton Ferry Terminal and spend a day cycling, sunbathing, or kayaking around the islands—ideal for fun, active things to do. Pack a picnic and enjoy the breathtaking skyline views, or rent a boat if feeling adventurous. Staying at nearby vacation rentals or holiday rentals near the harbor ensures quick access for your island adventure. Plus, the islands provide gorgeous scenery perfect for flirty photo shoots with your friends. Check ferry schedules and activities at Toronto Islands ferry service.
5. Discover the Art in Graffiti Alley
If vibrant street art and things to do that showcase Toronto’s edgy culture are your vibe, then a stroll through Graffiti Alley is essential. This colorful hotspot features large murals created by local artists, perfect for a fun, active walk and stunning backdrops for social media posts. Combine this with a short-term rental stay nearby so you can come back to explore more of the city's places to stay in. Destinations like Queen West and Kensington Market are also fantastic for exploring cool shops, vintage boutiques, and hidden cafes—ideal for a holiday with friends. Find more about local art tours and things to do at Toronto Arts & Culture.
6. Embrace Nature at High Park and Trails
For a balance of urban excitement and outdoor activity, spend part of your weekend in High Park. Stroll along extensive trails, hike up to the Grenadier Pond, or simply relax amidst lush greenery. This is a fantastic places to stay in close to nature—especially if you love active holidays that include running, yoga sessions outdoors, or bird-watching. Pack a picnic and enjoy a fun, flirty afternoon in nature with friends. Look into nearby holiday accommodation options that blend city convenience with outdoor serenity.
7. Indulge in Toronto’s World-Class Cuisine
No trip to Toronto is complete without exploring its diverse culinary scene. From trendy brunch spots to rooftop bars with stunning skyline views, there’s something for every palate. Book a holiday rental in the downtown area where you can stay close to top-notch things to do—and enjoy evening cocktails and bites after your daytime adventures. Experience fun, flirty dining at places like Northern Crown, or join a food tour to sample multiple cuisines. These gastronomic adventures are perfect for single travelers who love to mingle and enjoy the local vibe.
8. Participate in a Toronto Pub Crawl or Nightlife Tour
Nightlife is an integral part of a holiday in Old Toronto. Join a guided pub crawl through Queen West or King Street West and experience the best local activities for sociable, flirty fun. These tours often include exclusive access to trendy bars and speakeasies, offering the chance to meet fellow travelers. A convenient vacation rental nearby ensures you can keep the party going or head back at your convenience. Check out Toronto Life Nightlife for upcoming events and recommended hotspots.
9. Tour the Royal Ontario Museum
For an educational yet fun things to do, visit the Royal Ontario Museum. Explore diverse exhibits—from dinosaurs and ancient civilizations to natural sciences—which make for interesting conversation starters. This cultural experience pairs well with your active, curious personality and gives a perfect blend of leisure and learning. Staying in a centrally located short term rental will give you easy access to this iconic attraction, and afterward, you can unwind at nearby cafés or parks. Check out Royal Ontario Museum for current exhibits and special event nights.
10. Wrap Up Your Weekend with a Sunset at the CN Tower
No visit to Toronto is complete without soaking in the panoramic views from the CN Tower. Opt for sunset hours to see the city light up as the day ends—ideal for dreamy, flirty photos. Book a dinner reservation at 360 Restaurant to dine with a view, or simply enjoy the observation deck for free if you prefer an active exploration. Your stay in a centrally located holiday accommodation means quick access to this iconic landmark. End your memorable weekend on a high note with breathtaking things to do that leave you excited for your next visit.
For seamless planning and booking your perfect holiday accommodation at in Old Toronto, explore options at Search and Stay. They offer a wide range of rentals tailored to active, fun, and adventurous travelers like you, making it easy to customize your stay in this dynamic city. Whether you're after a cozy short term rental, a trendy apartment, or a luxurious condo, you'll find the perfect base for your weekend of exploration and fun.