Romantic Fall Honeymoon in Oregon: Nature, Relaxation & Adventure

Day 1: Explore Portland

Portland, Oregon on September 22, 2025

9:00am

Breakfast at Tōv Coffee

Start your honeymoon with a cozy breakfast at Tōv Coffee, known for rich coffee and a relaxing atmosphere. It’s perfect for fueling your day in Portland.
USD15, 1h

10:30am

Visit Washington Park & Japanese Garden

Enjoy a peaceful stroll through Washington Park and visit the Portland Japanese Garden, a serene romantic spot with beautiful fall foliage, open daily 10am–4pm.
USD20, 2h

1:00pm

Lunch at Screen Door

Experience southern-inspired cuisine at Screen Door, a beloved Portland favorite known for flavorful dishes and a cozy atmosphere.
USD30, 1h

3:00pm

Explore recreational cannabis dispensaries

Visit a few highly rated dispensaries such as Serra or Farma to browse local cannabis products. Oregon has legalized recreational marijuana, making it easy to purchase responsibly.
USD50, 2h

5:30pm

Relax at The Nines Hotel Rooftop Bar

Enjoy sunset cocktails at this rooftop bar offering romantic city views and a great wine & cocktail list – perfect to unwind before dinner.
USD25, 1.5h

7:30pm

Dinner at Le Pigeon

Savor a French-inspired fine dining experience at Le Pigeon, a top romantic spot featuring creative dishes and an intimate vibe.
USD70, 2h
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Day 2: Columbia Gorge Hiking

Columbia River Gorge, Oregon on September 23, 2025

7:30am

Breakfast at Pine State Bakery

Enjoy freshly baked goods and strong coffee at this local Portland favorite to prepare for a day of hiking.
USD15, 1h

9:00am

Drive to Columbia River Gorge

Travel east 45 minutes to the Columbia River Gorge, known for its stunning waterfalls and forest trails, ideal for romantic hikes and nature photography.
USD10 fuel, 45m

10:00am

Hike Multnomah Falls and surrounding trails

Visit one of Oregon’s most iconic waterfalls and explore nearby hiking trails for various difficulty levels, open dawn to dusk.
Free, 3h

1:30pm

Lunch at Multnomah Falls Lodge

Dine with views of the falls at the lodge’s restaurant, enjoying locally-sourced American fare and rustic ambiance.
USD30, 1h

3:00pm

Relax at Hood River Fruit Loop

Spend the afternoon driving the scenic Hood River Fruit Loop, visiting orchards and cideries with numerous spots to relax and enjoy local produce and drinks.
USD30 cider tasting, 3h

7:00pm

Dinner at Celilo Restaurant & Bar

Enjoy modern Northwest cuisine with a focus on fresh ingredients in a romantic setting in Hood River.
USD60, 2h
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Day 3: Willamette Valley Vineyards

Willamette Valley, Oregon on September 24, 2025

8:00am

Breakfast at The Waffle Window

Start your day with delicious creative waffles, a popular stop in Portland before heading to the vineyards.
USD15, 1h

9:30am

Drive to Willamette Valley

Travel south about 1.5 hours to Oregon’s premier wine region, famous for Pinot Noir and picturesque landscapes.
USD15 fuel, 1h30m

11:30am

Wine tasting at Domaine Serene

Visit this exquisite vineyard for wine tasting and tour, offering breathtaking vineyard views and award-winning wines.
USD40, 2h

2:00pm

Lunch at Red Hills Market

Enjoy artisanal sandwiches and farm-to-table salads at this charming spot in Dundee, perfect for a casual and tasty lunch.
USD25, 1h

3:30pm

Explore other wineries or romantic countryside drives

Spend the afternoon visiting another winery such as Sokol Blosser or simply enjoy the vineyard landscapes driving through the valley.
USD30 tasting, 3h

7:30pm

Dinner at JORY Restaurant

Indulge in fine dining paired with local wines at JORY, an elegant yet cozy restaurant set within the Allison Inn & Spa.
USD70, 2h
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Day 4: Relax and Spa Day

Willamette Valley, Oregon on September 25, 2025

8:00am

Breakfast at the Inn

Enjoy a relaxing breakfast at your accommodation, focusing on fresh and local ingredients to start the day slow.
USD20, 1h

9:30am

Couples Spa Treatment at Allison Inn & Spa

Indulge in a romantic couples massage and spa experience, with serene surroundings and top-notch treatments. Book in advance.
USD200, 2h

12:00pm

Light lunch at the spa café

Enjoy a healthy, light lunch offering fresh salads and seasonal ingredients to complement your relaxing day.
USD25, 1h

2:00pm

Leisure walk or small hike at nearby nature trails

Take a gentle hike or walk around the scenic McMinnville or Dundee area, famous for its peaceful beauty and fall colors.
Free, 2h

6:00pm

Dinner at Nick’s Italian Café

End your relaxing day with authentic Italian cuisine in a cozy, romantic atmosphere known for fresh pasta and local ingredients.
USD60, 2h
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Day 5: Travel to Bend & Explore

Bend, Oregon on September 26, 2025

8:00am

Breakfast at Over Easy Cafe

Fuel up with hearty breakfast fare at this Bend favorite, beloved for its cozy ambiance and delicious plates.
USD15, 1h

9:30am

Drive to Bend

Travel east for approximately 3 hours to reach Bend, a scenic town famous for outdoor sports and mountain views.
USD30 fuel, 3h

1:00pm

Lunch at Jackson’s Corner

Enjoy Southwest-inspired American lunch with fresh ingredients in a warm, inviting setting in downtown Bend.
USD25, 1h

2:30pm

Visit Smith Rock State Park

Explore this iconic rock climbing and hiking area offering stunning high desert views and moderate to challenging trail options. Park is open sunrise to sunset.
USD5 park fee, 3h

6:00pm

Dinner at Zydeco Kitchen & Cocktails

Sample delicious Cajun and Southern dishes with creative cocktails—a lively and romantic spot to unwind after hiking.
USD60, 2h
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Day 6: Outdoor Adventures & Downtown Bend

Bend, Oregon on September 27, 2025

8:00am

Breakfast at Chow

Start your day with a popular breakfast spot featuring farm-fresh ingredients and a range of classic and creative dishes.
USD15, 1h

9:30am

Hiking or Mountain Biking at Tumalo Falls

Visit Tumalo Falls for an easy to moderate hike or rent mountain bikes to explore. The falls offer picturesque views and peaceful nature, open dawn to dusk.
USD5 parking, 3h

1:00pm

Lunch at Barrio

Taste flavorful Latin street food with a modern twist in a vibrant atmosphere in downtown Bend.
USD25, 1h

3:00pm

Relax and browse boutiques downtown

Explore Bend’s charming downtown with unique shops, art galleries, and coffee shops - perfect for strolling hand in hand.
Free, 2h

5:30pm

Enjoy drinks at a local brewery like Deschutes Brewery

Sample craft beers from one of Oregon’s top breweries, known for its cozy atmosphere and excellent variety.
USD20, 1.5h

7:30pm

Dinner at Ariana Restaurant

Dine at this highly rated Bend restaurant serving creative contemporary American cuisine with a romantic ambiance.
USD70, 2h
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Day 7: Return to Portland & Farewell

Portland, Oregon on September 28, 2025

8:00am

Breakfast at Thump Coffee

Enjoy quality coffee and pastries from one of Portland’s favorite local roasters before heading back to the city.
USD15, 1h

9:30am

Drive back to Portland

Drive approximately 3 hours back to Portland to prepare for your flight home, enjoying final scenic views along the way.
USD30 fuel, 3h

1:00pm

Lunch at Pine Street Market

Share a casual but delicious lunch at this lively food hall featuring multiple vendors and flavors reflecting Portland’s creative food scene.
USD30, 1h

3:00pm

Last walk at Tom McCall Waterfront Park

Take a romantic stroll along the Willamette River at this iconic Portland park to reflect on your honeymoon memories, open daily dawn to dusk.
Free, 1h

5:00pm

Head to Portland airport

Allow plenty of time to return your rental and check in for your flight, concluding your scenic and romantic Oregon honeymoon.
USD0, N/A
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