A Sip and Stroll Is One of the Most Reliable Events You Can Run Downtown

The hard part is the logistics: selling tickets, managing check-ins across 10 or more venues, tracking participation, and building an audience you can actually reach again after the event ends. Here's how to pull it off well.

Plan the Basics First

Recruit 8 to 15 participating venues and give each one one job: offer a sample or small pour to ticket holders during the event window. A mix of wine bars, breweries, cocktail lounges, restaurants, and specialty shops gives people enough variety to plan an interesting route.

Pick your theme early. A wine walk, a cocktail crawl, a hot cocoa trail, a craft beer tour. The theme shapes everything from your promotional copy to which businesses you recruit. The clearer it is, the easier it is to sell tickets.

Set your ticket price between $25 and $45 depending on your market and what's included. Lock in a date at least six weeks out so you have time to promote properly and give your venues time to plan their pours.

Sell Tickets Without the Third-Party Fees

Proxi's event ticketing lets you sell directly. You set the price, you keep more of the revenue, and your attendees stay in your ecosystem from purchase to event night. No sending people to a third-party platform and hoping they come back.

Check People In When They Arrive

On the night of the event, your team will soon be able to check attendees in directly through Proxi. Verify their ticket, hand over a wristband or digital pass, and get people moving, all in one step. No paper lists, no juggling a separate scanning app.

Map Every Stop with What's Being Poured

Build your sip and stroll map in Proxi with a pin for each venue that includes what they're serving that night. Wine, craft beer, cocktails, non-alcoholic options. Tag each stop so attendees can filter to the drinks they want and plan their route accordingly. This is the detail people actually care about when they're deciding how to spend their evening, and it's the kind of information a static flyer can never give them.

Default to Walking Directions

Your attendees are already downtown. Set your map to walking directions by default so they can move from stop to stop without adjusting anything. Small detail. Makes a real difference in the overall experience.

Add a Passport Challenge to Drive Participation

Set up a Passport Challenge in Proxi so attendees can check in at each stop and earn stamps. Offer a prize for completing the full route or a discount at a participating business. People working toward a goal visit more stops, stay out longer, and generate more revenue for your district's businesses. It also gives you cleaner data on how many people actually made it through the full event.

Promote It Early and Build Anticipation

Sip and strolls sell out when you start promoting early. Here's a timeline that works:

• Six weeks out: Announce the event and open ticket sales. Early-bird pricing rewards fast buyers and creates urgency.
• Four weeks out: Reveal your participating venues and what they're pouring.
• Two weeks out: Email your list with a reminder and a link to buy tickets. Include the map if it's ready.
• One week out: Post a preview of the route and build anticipation on social.
• Day of: SMS blast to your subscribers with the check-in location and start time.

Proxi's email and SMS tools let you run this entire promotional sequence from one platform. Every send grows your list and warms up your audience for the next event.

Share the Map Everywhere in One Step

Your sip and stroll map can be shared as a link, embedded on your website, or accessed via QR code on flyers, posters, and social posts. Update a venue or change a pour detail once and it updates everywhere automatically. No chasing down outdated PDFs the morning of the event.

Collect Emails and SMS from Every Attendee

Every ticket buyer and every check-in is a potential subscriber. Proxi captures contact info so you can reach your attendees again. Post-event, send a follow-up with a recap, a spotlight on a participating venue, or early-bird access to the next one. The attendees who showed up once are your warmest audience for every event you run after this.

Get Analytics After the Event

See which stops were most popular, when attendance peaked, and how many people completed the full route. Bring those numbers back to your participating businesses and sponsors. Real data from a real event is how you grow participation and revenue year over year, and how you make the case for a bigger sponsorship budget next time.

What to Expect Your First Time

The first sip and stroll is your proof of concept. Ticket sales may be slower than you'd like because people don't know what to expect yet. That's normal. Focus on running a smooth event: the check-in is easy, the map works, the venues are ready. A great first event is your best marketing for the second one.

By your second or third year, you'll have a list of past attendees, a reputation in your community, and businesses asking to be included rather than needing to be recruited. That's when the event starts compounding. Start building toward that from day one.