Sipping & Playing in Jacksonville – September 2026

I THOUGHT I KNEW the names of most of the wineries within an hour of Jacksonville.

As it turns out, I was wrong.

One short ride with Robbie Ross, co-owner of Wine Hopper, introduced us to Dwell, put Wanderlust on our must-visit list, and reminded me that Southern Oregon’s wine scene is much bigger than the places we visit again and again.

We only had a few hours to spare, so instead of experiencing one of Wine Hopper’s signature tours, Robbie invited us aboard her comfortable Mercedes Sprinter van for a quick outing. It was just enough time to get a glimpse of what makes Wine Hopper so special and why so many locals and visitors trust Robbie to show them the best of Southern Oregon wine country.

Our destination was Dwell, a winery we had somehow never visited despite years of exploring the Rogue Valley. Nestled among the vineyards, Dwell immediately charmed us with its beautiful tasting room overlooking the vines. It felt intimate, relaxed, and welcoming. It was the kind of place you could easily spend an entire afternoon. Our group’s unanimous favorite was their sparkling rosé, which paired perfectly with the peaceful setting.

As we drove, Robbie shared stories about wineries throughout the region and casually mentioned several, including Wanderlust, that we had never even heard of. It quickly became clear that Wine Hopper is much more than transportation. Robbie takes care of every detail, from recommending wineries and building a personalized itinerary to making reservations and coordinating special requests. All you have to do is climb aboard, relax, and enjoy the day.

Founded in 2012 and co-owned by Robbie since 2018, Wine Hopper offers private three-hour tours and two five-hour experiences: one with lunch and one without. No matter which tour you choose, tasting flights at each winery are included. Every itinerary is customized around your group’s interests, whether you enjoy sparkling wines, bold reds, scenic vineyards, or boutique tasting rooms. It’s a fun, stress-free way to experience Southern Oregon wine country while leaving the driving, planning, and reservations to Robbie.

For Jacksonville locals, Wine Hopper is the perfect excuse to venture beyond our favorite neighborhood tasting rooms and discover something new. It is ideal for birthdays, girls’ weekends, anniversaries, entertaining out-of-town guests, or simply spending a carefree afternoon exploring wineries you may have otherwise missed.

The best part? Wine Hopper operates year-round, so there is always a reason to explore. You can learn more or book your tour directly at www.winehoppertours.com.

I may have thought I knew the names of most of the wineries nearby, but thanks to Robbie and Wine Hopper, I left with a new favorite in Dwell and a growing list of places I cannot wait to visit. Sometimes the best adventures are the ones that remind us there is still so much to discover right here in our own backyard.

Disclaimer: I’m just a wine-loving mom with no formal wine education. Just a mission to find the best places to sip, stay, and savor in Southern Oregon.