Born from a wine import business and shaped by deep relationships with multi‑generational wineries, Joy of Wine Journeys built a premium, multi‑day model with a ~75% repeat rate. Natalie shares why they skip big cities, how “depth over density” creates value, and how pricing, partnerships, feedback, and tight ops compound into growth.

Top 10 takeaways

1) Repeat guests keep coming back. About 75% rebook, often bringing friends and family. Nail the first trip and lifetime value follows.

2) Win the in between. Don’t try to run Paris or Venice. Guests fly into a gateway, then the tour connects the regions in between where long winery relationships unlock access and stories.

3) Fewer stops, deeper moments. Five wineries in ten days. Hosted visits. Family meals. Time to linger. People remember conversations and rituals, not mileage.

4) Price for the value you deliver. Raise prices as the experience improves. Let booking behavior and guest comments set the ceiling, not nerves.

5) Partners make you resilient. When a bus failed, local partners mobilized vans, cold water, and support within the hour. Good relationships turn problems into loyalty moments.

6) Feedback is the roadmap. Debrief during and after each tour, then keep, change, or cut. Trim bloat, smooth pacing, and upgrade hotels, meals, wines, and transport.

7) Know who you serve. Average age ~63. Well traveled. Hungry for hosted, exclusive experiences without snobbery. Design pacing, teaching, and access for that person.

8) Confirm, confirm, confirm. Book a year out, then reconfirm at six months, three months, one month, and day‑of. Fewer surprises. Smoother days.

9) Help in the cities even if you don’t operate there. Refer guests to vetted guides in Venice, Milan, Paris, Nice, and Florence so the whole trip feels looked after.

10) Use tech to support margins, not as the magic. TravelJoy for CRM, WeTravel for euro payments, Travelfy for itineraries, QuickBooks for the back office. The differentiator is still access, hosting, and relationships.