If your group chat has been stuck on "what are we doing this weekend?" for days, you're not alone. Toronto has no shortage of options, but the best girls night out is the one that's easy to coordinate, fun for different tastes, and memorable enough that everyone wants to do it again.
Wine Fest Toronto was built for that exact sweet spot: one indoor venue, a lively crowd, music and photo moments, and a lineup of wines and drinks you can explore at your own pace.
Instead of locking yourselves into one restaurant table all night or bouncing between bars hoping the vibe is right, Wine Fest gives your group a choose-your-own-adventure night out. You can taste, chat, regroup, dance, and wander booth to booth without the awkward "where should we go next?" debate.
And because Wine Fest uses a digital drink token system, everyone can decide what to try and how quickly to move. That makes it far easier to plan for a group with different budgets and preferences.
This page is your practical guide to planning a girls night out in Toronto at Wine Fest, including a simple arrival plan, meet-up tips that prevent the classic "I'm at the entrance... no, the other entrance" spiral, and a tasting strategy that keeps the night flowing.
When you're ready, grab tickets at our Spring page.
Built-in energy without the bar-hopping logistics. A classic girls night out in Toronto can turn into a full-time coordination project: pick the neighborhood, pick the place, fight for a reservation, wait for a table, decide where to go next, then repeat. At Wine Fest, you get one venue with multiple areas to explore, so the night feels dynamic without needing to travel between stops.
A social experience that still lets you talk. The best nights out aren't just loud music and a packed room. They're the moments your group actually connects: the "try this" sip swap, the shared laugh when someone discovers a new favourite, the quick recap after a round of tastings.
Flexible pacing for mixed tastes. Some friends want to taste everything. Others want a slower, curated approach. Some are wine lovers, some are spirits people, and some just want a fun, grown-up night out with good vibes. The digital drink token system makes that variety easy.
Photo moments that don't feel staged. Wine Fest delivers plenty of natural opportunities: the first cheers, the booth-to-booth stroll, the group photo when everyone's feeling their best, and the end-of-night shot that proves you actually made it out together.
Food is available for purchase if you want a bite and snack when you need to, then keep the night moving.
The best part is that it's naturally social. You can mingle with your group, chat with vendors, and keep the night feeling active without having to make constant decisions about where to go next.
Pick a session and commit. The fastest way to derail a girls night out is leaving the decision open too long. Choose a session that works for the majority, then buy tickets early so everyone is locked in. Share the link in your group chat: Spring Edition. If you're deciding between editions, visit the current edition page (Spring or Holiday) to confirm dates and details.
Assign a group captain. One person doesn't need to plan everything, but one person should handle the essentials: ticket link, session time, and the meet-up plan. A quick pinned message in the chat saves you from answering the same question twelve times on event day.
Create a meet-up point that can't be misunderstood. "Inside" is not a plan. "By the entrance" is not a plan. Choose a specific landmark you can describe in one sentence, like "right after check-in" or "beside the main Wine Fest Toronto sign." If you have friends who run late, pick a second meet-up time 30 minutes after doors so no one feels stressed.
Check in, get oriented, and buy your digital drink tokens if you forgot to ahead of time — learn more about how tokens work. Because Wine Fest uses a digital drink token system, it's smart to start with a modest token bundle and add more later if your group wants to keep tasting. This keeps budgets under control and prevents over-ordering at the start when everyone's excited and moving fast.
For groups, the easiest way to keep everyone happy is to begin with crowd-pleasers: a crisp white, a refreshing rosé, a sparkling option, an easy spirit, RTD or beer. Starting with lighter flavours helps you warm up your palate and gives your group time to settle in.
The "Sip-Swap" method (best for groups): If your friends are open to sharing tastes, rotate who chooses the next booth. One person picks a drink they're curious about, everyone takes a small sip, then you move on. This stretches tokens, increases variety, and keeps the experience interactive.
A tasting plan that doesn't feel like homework: Think in mini-themes. Try a "Canada round" early, a "Europe round" later, or alternate between wine and spirits. If your group loves structure, decide on three categories before you arrive. If you're more spontaneous, follow the vibe and let curiosity lead.
If you want an easy theme without overthinking it, try this flow: start with something crisp, move into something fruit-forward, then end with one "bold pick" someone in the group is curious about. It keeps the night feeling intentional while still letting you explore freely.
Build in one regroup break every hour. Group nights out are won or lost based on pacing. Set a casual rule: after every few tastings, your group meets at the same spot for five minutes. Use it for water, quick photos, and the classic "okay, what's the best thing we've had so far?" recap.
Know when to pivot. If a booth has a longer line, don't let it stall the whole group. Split into two pairs for ten minutes and meet back at the regroup point. This keeps the night moving without anyone feeling abandoned.
End on a high note. Choose one last "group favourite" pour, take your final photo while everyone still looks fresh, and plan your exit before you start saying goodbye. If your group wants more details on timing, entry, and on-site policies, check our essentials page and FAQ section before the event day.
Decide what "after" looks like. Some groups head home happy. Some want one more stop. The best move is agreeing in advance: either you're doing a clean finish after the festival, or you're choosing one nearby option so the night stays cohesive.
Meet-up point ideas that actually work: Choose something that's fixed and easy to describe. Examples include "right beside coat check," "at the first photo backdrop after check-in," or "by the entrance." Put the meet-up point in the group chat twice: once when you buy tickets and once on the day of the event.
Group pacing tip: Don't start the night with everyone trying to coordinate every pour. The easiest flow is two mini-groups for the first round, then regroup and swap recommendations. People feel more free to explore, you avoid crowding a single booth, and you'll end up with a better list of "must try" drinks for the second half of the night.
Safety and logistics: Keep it simple and proactive. Make sure everyone has a charged phone, agree on a rideshare or TTC plan before the end of the night, and remind the group that it's okay to take breaks. If you have questions about venue rules, accessibility, or on-site services, our FAQ section is the quickest place to confirm what applies to your session.
Aim for photo-ready, comfortable, and hands-free. Wine Fest is an indoor event where you'll be walking, standing, and holding a glass, so the best outfit is the one that looks great and feels easy.
For the "dress up" crew: A midi dress, jumpsuit, or a sleek top with high-waisted pants works perfectly. Choose shoes you can stand in for a few hours. If you love heels, consider a block heel or a lower height. Your feet will thank you before the night is over.
For the "cute but casual" crew: Dark jeans, a statement jacket, and a clean sneaker or ankle boot is a classic Toronto girls night out uniform. It photographs well, it's comfortable, and it fits the festival vibe.
Bring layers. Indoor temperature can shift depending on crowd size. A light jacket, blazer, or stylish overshirt keeps you comfortable without ruining your look.
Go easy on heavy perfume. Strong scents can compete with the aromas of wine and spirits. Keep your essentials minimal: phone, ID, card, and anything you need to stay comfortable. A small crossbody bag is ideal.
Friday evenings: The energy is higher and the crowd is ready to start the weekend. If your group wants music-forward vibes and a more social atmosphere, this is usually the sweet spot.
Saturday sessions: Expect peak festival energy. It's ideal for bigger groups, bachelorettes, and anyone who wants the full "Toronto event" feel. If you have a mix of personalities, set the regroup point rule early so nobody gets separated in the excitement.
Sunday sessions (Spring Edition): A more relaxed pace with lots of people who came specifically for tasting. It's a great option for groups who want a calmer vibe, more conversation time, and a more "sip and explore" experience.
Spring Edition vs. Holiday Edition: Both are indoor, but the vibe changes with the season. Spring feels like a fresh start after winter and works perfectly for celebrations, birthdays, reunions, and "first patio season" energy without being outside, or simply something to do! Holiday feels like a year-end celebration, with festive momentum and a calendar full of reasons to gather. Either way, it's a strong pick for a girls night out in Toronto that's easy to coordinate.
The simplest group rule: everyone buys tickets for the same session. It sounds obvious, but split sessions are the number one reason groups end up disappointed. Send the ticket link to your chat, set a deadline, and keep it moving.
If your group is 6-10 people, consider collecting confirmations early. Ask everyone to screenshot their ticket confirmation so the captain can quickly verify who's in. This isn't about controlling people, it's about preventing the last-minute "I thought I bought it" surprise.
If you're planning for 8+ people, use the group contact option. Bigger groups sometimes need help coordinating arrival timing, meet-up points, or purchasing together. Planning for a group? Contact us.
Remember that drinks are managed through digital tokens. That's a win for groups because spending can stay flexible. Some friends will want to taste more. Others will keep it light. Tokens make it easy for everyone to have a great night without feeling pressured to match someone else's pace.
Before event day, skim our essentials page for the full overview and FAQ section for the quick answers that usually show up in the chat: arrival timing, age policy, and venue details. If you want social proof to share with friends who need convincing, send them @winefesttoronto on Instagram so they can see what the event actually looks like.
If you're celebrating something specific (birthday, bachelorette, reunion), make it feel "event-like" without adding stress: pick a session, choose one photo moment to aim for, and keep the rest flexible. The night is better when you're present, not managing a schedule.
No. Wine Fest uses a digital drink token system. Your ticket gets you into the event for your selected session, and you choose which drinks to purchase with tokens.
Arriving close to the start of your session gives your group more time together, but you can typically arrive within your session window. If you want the smoothest experience as a group, plan to arrive within the same 20-30 minute window.
Pick a clear meet-up point and set a second regroup time. If you're worried about timing, have the early arrivals start with a water break and one "warm-up" tasting, then meet the rest of the group before you go deeper into the festival.
Not at all. Wine Fest is designed for a mix of preferences and to discover new things. Your group can explore wines, spirits, and other drink options, so everyone can find something they enjoy.
It depends on how much your group wants to taste. Use the sip-swap method to maximize variety, then add tokens if you want to keep going.
Yes, there are food options available for purchase, but Wine Fest is primarily a drinks and experience event. If your group wants a full dinner plan, consider meeting for food before or after the festival rather than relying on it as the main meal.
Yes. It's one of the easiest Toronto options for celebrations because it's a single venue with built-in atmosphere. For larger groups, use the group contact option so we can help you plan.
Set the regroup point rule. Choose a landmark near the main area and make it the default meeting spot. Most groups that do this never lose anyone for long.
Use our essentials page for the full overview, FAQ section for quick policy answers, and an email to all ticket holders gets sent out the day before with details.
Stop settling for the same girls night out routine where half the group ends up bored, the other half is trying to change locations, and everyone spends more time coordinating than enjoying. Wine Fest Toronto makes the night easy: one indoor venue, a fun crowd, plenty to explore, and the flexibility of a digital token system so your group can choose your own pace.
Start with the basics: pick a session, send the ticket link to the chat, and set a clear meet-up point. Then use our essentials page and FAQ section to eliminate last-minute questions. If you want to help friends visualize the vibe, share @winefesttoronto on Instagram for social proof.
Get your tickets, make it official, and turn "we should do something soon" into a real plan. And if you're coordinating a bigger group, use the group contact option so we can help you pull it together without the stress.
Wine Fest Toronto runs twice yearly at Heritage Court at Enercare Centre, with Spring and Holiday editions that are both indoor. No matter the season, it's the kind of Toronto outing that feels like an event, not just another stop on your usual list.
