Girls’ (or Guys’) Weekend in Ontario: Fun-Filled Itineraries for Every Crew
A getaway with your best friends is more than just a break—it’s a chance to recharge, reconnect, and make memories that last long after the weekend ends. Whether your ideal escape includes wine tastings and spa robes or paddleboards and pints, Ontario has a destination for every crew. Here’s how to plan the perfect girls’ or guys’ weekend across the province—from laid-back countryside charm to big-city thrills.
Wine & Wellness in Prince Edward County
Prince Edward County is Ontario’s go-to region for wine lovers and boutique vibes. A favourite among friend groups for its balance of scenic views and gourmet experiences, “The County” makes it easy to switch off and settle in.
Start your weekend at Grange of Prince Edward or Closson Chase, where you can sip on local vintages while gazing out at rolling vineyards. Looking for bubbly? Hinterland is known for its sparkling wines. Plan a relaxing itinerary that includes browsing Bloomfield’s artisan boutiques, grabbing farm-fresh ice cream at Slickers, or lounging on the beach at Sandbanks Provincial Park.
Add wellness into the mix with a yoga session or massage at Bloom Holistic Retreat. Evenings call for upscale meals at The Marans or The Drake Devonshire, followed by bonfires and stargazing back at your inn or rental.
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| Best for: | Sipping, pampering, and exploring small-town charm |
| Where to stay: | Lakeside Airbnbs, the June Motel (Instagram-worthy), or Merrill House for boutique elegance. |
| Insider tip: | Rent bikes and cycle the Millennium Trail for a leisurely tasting route connecting wineries and cideries. |
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Muskoka Lakehouse Escape
A cottage weekend in Muskoka is the classic Ontario escape—and for good reason. With its glittering lakes, towering pines, and charming towns, it’s an ideal setting to unplug and bond.
Rent a multi-bedroom lakehouse near Bracebridge, Gravenhurst, or Huntsville, and set your group up for a stress-free stay: firepit, dock, and hot tub included. Spend your days kayaking, paddleboarding, or simply sunbathing with a drink in hand. When you’re ready to explore, browse the weekend farmers’ markets or take a scenic hike in Arrowhead or Hardy Lake Provincial Park.
If your group includes a mix of early risers and night owls, no worries—there’s room for both sunrise paddles and wine-fueled board games into the evening.
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| Best for: | Fireside chats, cozy vibes, and outdoor chill |
| Where to stay: | A fully stocked Airbnb or private resort lodge with space for groups. |
| Insider tip: | Book a private chef or meal delivery from a local caterer so no one has to cook. |
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Urban Adventure in Toronto
If your group thrives on energy, culture, and cuisine, a weekend in Toronto packs in everything you could want—plus a few surprises. Start your stay at a cool downtown hotel like The Bisha, 1 Hotel Toronto, or the Drake Hotel.
Kick things off with brunch at Lady Marmalade or Cafe Landwer, followed by retail therapy on Queen Street West or a vintage hunt in Kensington Market. Pose for photos at Graffiti Alley, hit up the AGO or ROM, and treat yourselves to massages at Body Blitz Spa.
Come nightfall, Toronto delivers. Choose from rooftop bars, drag brunches, live theatre, or hidden speakeasies. Whether you’re dancing in the Village or sipping wine in Yorkville, your group will find a vibe that suits.
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| Best for: | Foodies, nightlife lovers, and cultural explorers |
| Where to stay: | Hotels with rooftop lounges or suites for groups, like Hotel X or the Ace Hotel. |
| Insider tip: | Book a private group cooking class or cocktail workshop for a hands-on experience. |
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Brewery Trails in Southwestern Ontario
Craft beer lovers will find plenty to toast to across Southwestern Ontario, where small towns are brimming with character and great brews. Start your route in London with a stop at Anderson Craft Ales or Storm Stayed, then head toward Bayfield or Goderich for lakeside views.
Cowbell Brewing in Blyth is a destination in itself, with a massive facility, delicious food, and a tap list to match. Many breweries offer games, live music, and large patios—perfect for groups. Wrap up your weekend in Stratford, where you can walk the river path, enjoy fine dining, or follow the Bacon & Ale Trail.
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| Best for: | Beer fans, road trippers, and laid-back fun |
| Where to stay: | Rent a cottage near Lake Huron or book multiple rooms in a Stratford inn. |
| Insider tip: | Hire a designated driver or book a brewery tour van to keep it safe and fun. |
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Blue Mountain Wellness & Adventure
Looking for a blend of calm and excitement? Blue Mountain Village is a one-stop shop. Book a chalet, slope-side suite, or wellness retreat, and tailor your weekend to your crew’s energy.
Start the trip with hydrotherapy at Scandinave Spa, followed by lunch with a view at Oliver & Bonacini Café Grill. Hike to the Scenic Caves, rent e-bikes, or take on the Ridge Runner coaster. If you’re looking to relax, opt for a wine and cheese tasting or a float therapy session.
Evenings in the village mean live music, lively patios, and spa robes after dark.
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| Best for: | Spa days, adrenaline, and mindful moments |
| Where to stay: | On-resort suites, Airbnbs, or wellness retreats with hot tubs and fireplaces. |
| Insider tip: | Try an apple-themed excursion along the Apple Pie Trail, which includes cideries, bakeries, and local farms. |
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Make It Meaningful
Ontario’s diversity makes it easy to plan a getaway that fits your friend group’s style. Want to sip and spa? Chill and reconnect in the forest? Dance and dine in the city? You’ve got all the options—and most are just a few hours from home.
Whatever destination you choose, the best part is the company: inside jokes, road trip playlists, shared memories, and a weekend that feels like a breath of fresh air.