Travel Itinerary

Day 1

Private transfer from airport to hotel

The Heathman Hotel ★★★★ (3 nights)

Rest of the day at leisure to explore Portland and the West End

Dinner reservation at Ava Gene’s

Day 2

Portland foodie tour

Experience the heart of Portland’s culinary scene on this downtown foodie adventure. Some of the city’s biggest eating trends started here, from farm-to-table restaurants to PDX’s original food cart pod, making downtown an eater’s delight. On this walking food tour visit restaurants that are James Beard Award winners, Iron Chef competitors, and winners of Top Chef Masters. Come taste the very best of what Portland’s becoming known for, including fine dining, ground-breaking food halls, delicious brews, and more.

Rest of the day at leisure to go to Woodblock Chocolate

Dinner reservation at Toro Bravo
Day 3

Private garden tour with picnic

Embark on a quintessential Portland experience starting with a hike in Washington Park, offering stunning views of Mt. Hood and the serene Japanese Gardens. Explore the 62-acre Grotto, featuring beautiful gardens dedicated to Mary, with seasonal decorations like the Festival of Lights. Indulge in gourmet fare from Woodlawn’s P’s & Q’s Market before concluding your journey at Cathedral Park, dining beneath the majestic St. Johns Bridge on the Willamette River.

Dinner reservation at Le Pigeon

Day 4
Cannon Beach

Pick up car in Portland

Drive to Cannon Beach (about 1h30mins)

Stephanie Inn ★★★★ (2 nights)

Day 5

Columbia River Eco tour

Set sail from Astoria’s West Mooring Basin Slip D-5, under the majestic Astoria Megler Bridge. Enjoy the historic waterfront, spotting sea lions at Pier 39. Traverse Lewis & Clark’s routes through the Wildlife Refuge, encountering diverse wildlife. Glide through narrow channels to witness the railroad bridge, floating homes, and salmon nurseries. Conclude with close views of large oceangoing ships.

Day 6
Depoe Bay

Drive to Depoe Bay (about 2h15mins)

Stop on the way to enjoy some spots

Follow the Pacific and head south, admire the long wild beaches as you drive. Stop in Tillamook – Pacific City – Lincoln City.

Hotel Whale Cove Inn ★★★★ (1 night)

Day 7

Drive to Bandon (about 3hrs)

Enjoy your car ride to explore the surroundings

Head south to Newport, an authentic fishing town, to witness sea lion colonies and Oregon’s last wooden lighthouse, Yaquina Bay. Experience the thrill of exploring the Oregon Dunes on a one-hour dune buggy tour, offering informative, scenic, and fun adventures along 8 miles of dunes and 2 miles of ocean beach. Continue south to discover infinite beaches, rivers meeting the sea, and rich wildlife like elk at the Elk Game Reserve. Spend the night in Bandon, listen to the sounds of the surf, and watch the sunset over the Pacific.

Windemere On The Beach (1 night)

Day 8
Grants Pass

Drive to Grants Pass (about 2h40mins)

Enjoy your car ride to explore the surroundings

Drive southeast towards Grants Pass, a small western town nestled in a wilderness watered by the Rogue River, which is ideal for outdoor activities: hiking, fly fishing, kayaking or boat trip, nature is here in its purest form. Make a quick incursion into California, and visit the superb redwoods of Redwoods National Park.

Rafting descent of the Rogue River

Experience one of the American West’s most legendary whitewater adventures—the Rogue River. Traverse through the heart of the Rogue River Wilderness, where you’ll encounter intermediate rapids and tranquil pools. Keep your eyes peeled for wildlife, including deer, black bears, river otters, and a variety of bird species. With its mix of excitement and serenity, the Rogue River offers an unforgettable rafting experience suitable for adventurers of all ages.

Weasku Inn ★★★ (1 night)

Day 9

Drive to Prospect (about 1h15mins)

Enjoy your car ride to explore the surroundings

Explore southern Oregon and drive through vineyards and forests. Follow the banks of rivers while driving towards the increasingly mountainous landscape to the small town of Prospect, very close to the southern entrance to the park Crater Lake National Park.

Prospect Historic Hotel ★★★ (1 night)

Day 10
Crater Lake

Drive to Crater Lake (about 30mins)

Crater Lake boat tour with Wizard Island

Take a boat tour of Crater Lake’s unparalleled beauty, including a special stop at Wizard Island. Join a summer tour for a scenic cruise and 3-hour to explore the island’s wonders. Hike to the summit for panoramic views and discover the Wizard Island Summit Trail for an unforgettable Crater Lake National Park adventure.

Oxford Hotel ★★★★ (1 night)

Day 11

Drive to Fossil (about 5h40mins)

Enjoy your car ride to visit

Drive northeast through central Oregon through absolutely beautiful and varied landscapes. Visit the John Day Fossil Beds National Monument, a paleontology site where you can observe hundreds of fossils. The road continues with the Painted Hills in the background, whose colors seem surreal, undulating from mauve to ocher through green.

Wilson Ranches Retreat Bed & Breakfast(2 nights)

Day 12

Horseback riding

Immerse yourself in an authentic working cattle ranch experience on a scenic horseback ride, cattle drive, pasture move, riding for strays, or checking fence lines as the Wilson family has for seven generations. Enjoy a couple of hours in the saddle for spectacular views of the Columbia River Plateau, John Day Basin, and the Cascade Mountain Range.

Day 13

Rock climbing at Smith Rock State Park

Visit Smith Rock State Park, in the high desert of central Oregon. Along with the natural beauty and extensive trail system that draws thousands of visitors every year, Smith Rock is a world-renowned rock-climbing destination, known as the birthplace of American sport climbing. With the amazing variety of beginner through advanced terrain ranging from 40 to 400 feet, there’s something for everyone. No experience is required.

Day 14
Hood River

Drive to Hood River (about 2hrs)

The Mount Hood Railroad ride tour

Hop aboard the Mount Hood Railroad for a memorable journey through the scenic Columbia River Gorge valleys, beneath the majestic Mt. Hood in Oregon. This 17-mile round trip passes through Parkdale, The Dalles, Carson, Trout Lake, and Klickitat, offering stunning views of winter wonderlands or spring blossoms along the Hood River, weaving through forests, orchards, and vineyards.

Colombia George Hotel & Spa ★★★ (1 night)

Day 15

Drive to Portland (about 1hr)

Stop o the way to visit the town of Cascade Locks

Cascade Locks is home to the Sternwheeler Columbia Gorge, which hosts daily and nightly cruises. Catch all the action from Thunder Island with local craft beer or a handmade milkshake and enjoy the city’s unparalleled views. Bonneville Dam, a historical dam where you could observe salmon climbing fish in season.

The Heathman Hotel ★★★★ (1 night)

Day 16

Drop off car at airport

Fly home