Explore Oregon

11 Days

Starting in/Ending in: Portland, Oregon

Total driving distance approximately 1,006 miles


Oregon has it all – high desert country to the east, balmy coast to the west, and mountains, rivers and forests in between. You don’t have to look hard to find Oregon’s more obvious wonders. Scenic Byways wind through fantasy-like landscapes, mighty waterfalls plunge into crystalline pools and of course craft beer breweries inhabit nearly every town with a stoplight (and even a few towns without!) Go explore – find your own private Oregon while checking out unique places to put your head down at night!

Trip Highlights

  • Portland
  • Hood River
  • Painted Hills
  • Crater National Park
  • Wine Country
  • Pacific Ocean


Set against the backdrop of snow-capped Mount Hood, vibrant Portland is surrounded by natural beauty. This quirky, sustainable, eco-focused city is known for its distinctive neighborhoods, beautiful gardens, craft beer (more breweries than any other city!), indie music, great shopping (Oregon has no sales tax), and restaurants whose chefs celebrate the local bounty of fresh ingredients.

Overnight: Hotel Lucia, Portland, Oregon

Located at the crossroads of the spectacular Columbia River Gorge National Scenic Area and the magnificent Cascade Range and just an hour from Portland, Hood River is wildly gorgeous, offering outdoor recreation, dramatic vistas, historic landmarks, bountiful fruit and fantastic food, wine, beer and cider. Hood River is a four-season destination. Overnight the Hood River Hotel. Step back in time as you enter this fully restored historic hotel. Hood River's oldest hotel, it is listed on the National Register of Historic Places.

Overnight:  Hood River Hotel, Hood River, Oregon

Depart Hood River for to Oregon’s cowboy country - Fossil - to horseback ride and overnight and overnight at a working ranch. Wilson Ranches Retreat Bed and Breakfast opened 16 years ago to guests offering an opportunity to experience ranch living and the beauty of Eastern Oregon’s high desert. The bed and breakfast is in a historic 1910 Sears Roebuck Ranch House with six ranch style guest rooms and breakfast being the event of the day. Guests from all over the world have become a part of the Wilson Ranches family.

Overnight: Wilson Ranches Retreat (Complimentary Full Breakfast), Fossil, Oregon

After a locally sourced, home-cooked breakfast at Wilson Ranches Retreat, depart Fossil for Sisters with a stop at the Painted Hills in Mitchell. When you travel to the Painted Hills, you can see millions of years of history revealed in the layers of mountains of earth, one color at a me. The hills get their name from the delicately colored stratifications in the soil and the yellows, golds, blacks, and reds of the Painted Hills are best seen in the late afternoon. Once you see them for yourself, it’s pretty easy to understand why the Painted Hills are one of the “7 Wonders of Oregon”. After exploring the Painted Hills, depart for Sisters, Oregon, (aka "Sisters Country") - a wonderland of lakes, mountains and rivers, a paradise for hikers, fly fishermen, paddlers, mountain bikers, birders, skiers and horseback riders. Spend the night nestled among towering Ponderosa Pines at FivePine Lodge & Spa. With the personal touch of a bed and breakfast, the privacy of romantic, cozy cabins and all the amenities of a resort, FivePine is a unique and one of a kind Central Oregon romantic destination and is so much more than just a hotel.

Overnight: FivePine Lodge, Sisters, Oregon

Depart Sisters for Crater Lake National Park. Crater Lake National Park has inspired people for hundreds of years. No place else on earth combines a deep, pure lake, so blue in color; sheer surrounding cliffs, almost two thousand feet high; two picturesque islands; and a violent volcanic past. It is a place of immeasurable beauty, and an outstanding outdoor laboratory and classroom. Crater Lake is located in Southern Oregon on the crest of the Cascade Mountain range, 100 miles (160 km) east of the Pacific Ocean. It lies inside a caldera, or volcanic basin, created when the 12,000 foot (3,660 meter) high Mount Mazama collapsed 7,700 years ago following a large eruption. Generous amounts of winter snow, averaging 533 inches (1,354 cm) per year, supply the lake with water. There are no inlets or outlets to the lake. Crater Lake, at 1,943 feet (592 meters) deep, is the seventh deepest lake in the world and the deepest in the United States. Evaporation and seepage prevent the lake from becoming any deeper. There at many hikes around the lake…but for the more adventurous try the hike down to the boat launch. The lake from this view is even more of an incredible site. Overnight at the Prospect Historic Hotel. The hotel, at one time a Stagecoach stop, now is run as a Bed and Breakfast Inn, was built in the late 1880s and is listed in the National Register of Historic Places.

Overnight: Prospect Historic Hotel (Complimentary Full Breakfast), Prospect, Oregon

Life slows a pace or two in quaint, historic Jacksonville. Boutique and antique shops line Main Street. From hiking local trails to strolling amongst main street’s boutique shops it’s about living the good life and it’s about … food and wine. Jacksonville’s wineries six exquisite tasting rooms and wineries are within a mile of town settled amongst many fine and casual dining options. Overnight at the Jacksonville Inn. Housed in one of gold-rush Jacksonville’s early permanent structures, the Jacksonville Inn perpetuates the nostalgic romances of that era. Built in 1861, the walls of the dining area and lounge were built of locally quarried sandstone, and specks of gold are still visible in the mortar. The town is the first in America to be named a National Historic Landmark, and Jacksonville has preserved its 19th Century charm.

Overnight: Jacksonville Inn (Complimentary Full Breakfast), Jacksonville, Oregon

Depart Jacksonville for the Bandon, along the Oregon Coast. Life in Bandon is shaped by nature and the people who make their home in this corner of the Oregon Coast. Enjoy year-round fishing, cycling, golf, hiking, and beach going. Overnight at The Bandon Beach Motel. The property is situated atop a bluff at Coquille Point, a tsunami-safe headland jutting out into the ocean, with wide sweeps of sandy beach on either side and sea stacks scattered along its shores.

Overnight: Bandon Inn, Bandon, Oregon

Drive along highway 101 to Yachats. Nestled between the green forest and the blue sea, Yachats is still a small village where you can walk everywhere. Yachats residents are a quirky lot, full of curiosity and creative sparkle. They value their beautiful environment; they host festivals for music, mushrooms, and more; they build trails everywhere; they sponsor speakers and support youth activities. There is live music somewhere almost every night. Yachats is the center of the central Oregon coast. In every direction, you will find places to explore and adventures to experience. Cape Perpetua offers tiide pools, blow holes, whale watching, fungus finding, nature guides, and miles of trails. Spend the night and renew your spirit at Overleaf Lodge, where every luxurious room overlooks the magnificent Oregon coast. An oceanfront trail meanders from the lodge to beautiful vistas, tidal pools, sandy beaches, and hidden coves. Sunsets are framed in your picture window. Appreciate the unique artwork featured throughout the Lodge.

Overnight: Overleaf Lodge (Complimentary Continental Breakfast), Yachats, Oregon

Welcome to Oregon Wine Country! The Willamette Valley, Oregon’s leading wine region, has over two-thirds of the state’s wineries and vineyards, and is home to nearly 500 wineries. It is recognized as one of the premier Pinot Noir producing areas in the world. Other cool climate varieties such as Pinot Gris, Pinot Blanc, Chardonnay, Riesling, and Gewürztraminer are equally at home in the Willamette Valley. While the number of wine & wineries continues to grow, Willamette Valley winemakers have not lost their personal, handcrafted approach to making wine, or their desire to do things a little differently. And they are being recognized worldwide for their efforts. Check into your own trailer for a memorable overnight. The Vintages Trailer Resort is centrally located in the heart of the Willamette Valley, halfway between Dundee, Oregon and Historic Downtown McMinnville, Oregon. The trailers are grouped together in their own neighborhood within the 14-acre Willamette Wine Country RV Park. Vintage trailer rental is fun for the entire family and will be the highlight of your trip. Each trailer offers a unique lodging experience tailored to compliment your wine tasting, dining, and exploration. Holiday in style, relive the past, in the heart of Oregon’s wine country. 

Overnight: The Vintages Trailer Resort, Dayton, Oregon

More opportunities to explore Portland and of course some last-minute shopping!

Overnight: Hotel Lucia, Portland, Oregon

Day 11 :
Tour Ends

Trip Includes

  • 10 hotel nights at published hotels (or similar), local hotel taxes and resort fees (except where mentioned), travel tips, maps, and brochures. Complimentary Breakfast subject to change at the hotel’s discretion.

Trip Excludes

  • Rental car, gas, parking fees, porterage, flights, airport transfers, meals, unless otherwise specified in the tour description, park & attractions entrance fees, unless otherwise specified in the tour description, ferry charges, travel insurance.

You can send your enquiry via the form below.

From $ 3,078
/ Single Occupancy Room (1 Adult)
From $ 349
/ Child 17 years and under with 2 paying adults
From $ 3,078
/ Double Occupancy Room (2 Adults)

Trip Info