How to Create a Travel Itinerary (Featuring Sip & Stay in Southern Oregon Wine Country)

Creating the perfect travel itinerary can turn a good trip into an unforgettable one, especially when you’re planning a food and wine vacation or dreaming up one of the year’s best weekend getaways. Whether you’re organizing a romantic retreat, exploring Oregon wine country with friends, or simply craving a rejuvenating weekend getaway, having structure (without rigidity) is key. That’s where our Sip & Stay itineraries come in: thoughtfully curated, locally inspired guides designed to make planning easy.

Below, we’ll walk through how to create a travel itinerary from scratch and show how our Sip & Stay experiences can double as both inspiration and a ready-to-use plan.

1. Start With Your Travel Goals

Before opening your notebook or travel itinerary planner, take a moment to define the purpose of your trip.
Are you looking for:

• Relaxation and scenic drives?

• Immersive food and wine travel?

• A romantic escape and one of the top weekend getaways for couples?

• A bit of exploration balanced with downtime?

Sip & Stay itineraries are designed around different traveler styles, whether you’re curious, adventurous, or indulgent, making it easy to start with a theme and build from there.

2. Choose a Destination That Fits Your Style

Selecting the right location sets the tone for your entire trip. Southern Oregon’s combination of wineries, riverfront beauty, and farm-to-table dining makes Grants Pass an ideal hub for weekend getaways and multi-day food and wine vacations.

Our region offers:

• Boutique wineries with intimate tasting experiences

• Farm-to-table restaurants

• Easy access to nature

• Relaxed, uncrowded wine country vibes

It’s the perfect place to craft a getaway that’s both elevated and approachable.

3. Map Out Your Activities

A great travel itinerary includes a mix of must-do activities and room to breathe. Structure your days around geographic clusters to avoid unnecessary driving. For example:

• Morning: Coffee + quick stroll downtown

• Midday: Wine tasting + lunch

• Afternoon: Additional tasting or a local cultural stop

• Evening: Dinner, sunset walk, or hotel relaxation

Our Sip & Stay programs simplify this with a sample travel itinerary for each traveler type, complete with suggested timing, local favorites, and can’t-miss highlights.

4. Add Local Flavor

To make a trip truly memorable, weave in experiences unique to the region. In Southern Oregon, this might mean:

• Private tastings with winemakers

• A chef’s tasting menu

• Strolling through historic Grants Pass

• Exploring artisan shops and galleries

Our Sip & Stay itineraries highlight hyperlocal touchpoints so your weekend feels rooted in place, not just a checklist of activities.

5. Plan Logistics Early

Little details can make or break a trip. Think through:

• Winery reservations

• Lodging availability

• Seasonal hours

• Drive times between activities

• Where you want to splurge and where you want to keep things relaxed

The Sip & Stay itineraries take this stress away: they consider timing, pacing, and flow for you, making them ideal for travelers building itineraries for the first time or for seasoned planners who just want a head start. And Latitude Wine Tours handles all of your wine tasting reservations! We are experts in making your wine tour seamless and stress-free.

6. Keep Space for Spontaneity

Even the best itineraries need flexibility. Leave room for:

• A bonus tasting

• A scenic pull-off

• An extra cocktail

• A cozy afternoon nap

• Wandering local shops

Our itineraries offer structure while still giving you the freedom to follow your curiosity.

7. Let Sip & Stay Do the Planning for You

If you’d rather skip the work entirely, our Sip & Stay itineraries are curated to make planning intuitive and enjoyable. Each itinerary functions as a ready-to-use travel itinerary planner while remaining customizable.

They’re ideal for:

• Effortless weekend getaways for couples

• Last-minute weekend getaways

• Special-occasion trips

• Thoughtful food and wine travel

Each Sip & Stay itinerary includes lodging suggestions, curated winery visits, dining recommendations, and unique activity pairings, everything you need for one of the best weekend getaways in Oregon wine country.

Final Thoughts

Learning how to create a travel itinerary doesn’t have to be complicated. Start with your goals, choose a destination that fits your vibe, balance structure with spontaneity, and embrace the local flavor that makes a place special. If you want an effortless way to begin, our Sip & Stay itineraries offer thoughtfully curated, locally inspired plans for an unforgettable Southern Oregon escape.

Ready to start planning? Explore our Sip & Stay itineraries and discover your perfect weekend in Grants Pass.