Sip & Stay: Your Perfect Southern Oregon Wine Country Getaway

Planning an Oregon wine getaway should feel exciting, not overwhelming. That’s exactly why I created Sip & Stay: a set of curated overnight itineraries that pair boutique lodging with the best Oregon wine tours, handpicked winery visits, and local experiences that truly capture the charm of Southern Oregon wine country.

Whether you’re new to wine tasting or you’re the go-all-out type who loves private winery tours and behind-the-scenes access, Sip & Stay offers a simple, personal, and memorable way to explore the region.

Why Southern Oregon Is the Ultimate Wine Country Escape

When people think of wine tasting trips, their minds often jump straight to Napa or the Willamette Valley. But the wineries in Southern Oregon offer something more relaxed, more scenic, and more personal.

Here in the Rogue Valley and Applegate Valley, you’ll find:

• Family-owned and small-production Oregon wineries

• Welcoming tasting rooms surrounded by mountains and vineyards

• A huge range of grape varieties (70+!) thanks to diverse microclimates

• No need for complicated reservations or crowded tasting rooms

It’s the perfect setting for slow travel, scenic drives, cozy stays, and truly unforgettable wine tours.

What Makes Sip & Stay Special?

Sip & Stay itineraries were designed to give visitors an effortless, memorable way to explore the best Southern Oregon wineries without hours of planning or guesswork. Each itinerary pairs:

• A curated route of standout wineries in Oregon

• Seasonal food recommendations

• Stress-free planning with built-in free time

• Lodging that complements the overall experience

If you prefer a fully guided experience, you can easily add one of our private winery tours through Latitude Wine Tours. And if self-guided adventures are more your style, you’ll have everything you need for a meaningful and beautifully paced weekend.

Introducing the Sip & Stay Itineraries

Each Sip & Stay itinerary is crafted for a specific type of wine traveler, so you can choose the one that best fits your pace, personality, and palate.

For the Curious

Perfect for new wine lovers or anyone who prefers a relaxed introduction to the region. This itinerary focuses on approachable tasting rooms and scenic, easygoing routes. Expect welcoming hosts and thoughtfully chosen stops, ideal for first-time visitors or casual drinkers wanting a laid-back wine tour.

For the Explorer

Designed for the traveler who loves variety, discovery, and digging into the “why” behind what they taste. You’ll explore a wider range of wineries in Southern Oregon, experiencing different winemaking styles and learning how geography shapes the region’s wines. It’s a celebration of diversity, both in landscapes and in flavor.

For the Connoisseur

This is the elevated experience for guests who want the best of the best. Expect cellar-level access, high-end wines, and the private winemaker tastings. This itinerary spotlights exceptional wines, vineyard-specific expressions, and the artistry behind Southern Oregon’s top producers.

Thoughtfully Chosen Places to Stay

Each Sip & Stay itinerary is paired with lodging that enhances the experience. Think:

• Boutique lodging with local charm

• Stays near top Southern Oregon wineries

• Peaceful views, cozy rooms, and easy access to tasting rooms

The goal: comfort, character, and convenience, all with room to slow down and enjoy the journey.

Why Sip & Stay Works for Every Kind of Wine Traveler

Whether you’re planning a romantic weekend, a birthday celebration, or a solo retreat, Sip & Stay makes it easy to explore the best of wineries in Oregon—without the stress of planning. Perfect for:

• Couples

• Girls’ trips

• Food-and-wine travelers

• Weekend explorers

• Out-of-state visitors curious about Oregon’s “other” wine region

And because these itineraries can be customized, you can always add extra days with wine tasting tours, scenic stops, or special requests.

Ready to Sip, Stay, and Explore?

If you’ve been dreaming about a West Coast wine getaway that feels authentic, scenic, and personal, the Rogue Valley is calling. Sip & Stay offers curated, memorable access to some of the best Southern Oregon wineries, with experiences tailored to your tasting style and travel pace.

Explore the itineraries, book online, or reach out to us directly; we’d love to build the perfect weekend for you. Cheers to planning your next adventure in Oregon’s most welcoming wine country!