Legends, Landscapes & Coastal Charms: 11-Day Oregon Discovery
June 4 - June 14, 2026
Experience the best of the Pacific Northwest with Small Town Journeys' immersive 11-day adventure through Oregon's diverse landscapes, from Portland's urban charm to ancient redwoods and volcanic wonders.
View Detailed Itinerary
Journey Highlights
Ancient Redwoods
Immerse yourself in the majesty of Redwood National & State Parks with ranger-led talks and breathtaking hikes through Jedediah Smith and Lady Bird Johnson Grove.
Crater Lake Wonder
Marvel at America's deepest lake, formed in a collapsed volcano. Enjoy ranger presentations, scenic rim walks, and spectacular photo opportunities at this natural wonder.
Coastal Treasures
Explore Oregon's dramatic coastline featuring historic lighthouses, charming seaside towns, and pristine beaches from Astoria to Florence.
What's Included
Accommodations
10 nights in carefully selected hotels, from Portland's boutique Inn at Northrup Station to oceanfront lodging in Seaside and Crescent City.
Dining Experiences
Daily breakfast, 9 lunches, 5 dinners, and a farewell river cruise brunch. Experience Portland's famous food carts and local culinary gems.
Expert Guidance
Two experienced guides for groups over 25, ensuring personalized attention and insider knowledge throughout your journey.
All Entry Fees
Every activity, entertainment, and excursion included. Optional upgrades available for those seeking enhanced experiences.
$3,950 $3,950 for double-occupancy ($4,068 if paying by credit card) • $750 single supplement
Portland: Urban Charm & Culinary Delights
Begin and end your journey in Portland's vibrant neighborhoods. Upon arrival, settle into the boutique Inn at Northrup Station before embarking on a progressive dinner tour of Portland's famous food carts, sampling diverse cuisines with a local culinary expert.
On your final day, enjoy a farewell brunch cruise on the Willamette River before visiting the legendary Powell's City of Books – the perfect place to find literary treasures from your journey.
Boutique Accommodations
Stay at the Inn at Northrup Station, perfectly positioned near Portland's trendy NW 23rd district and Pearl District.
Culinary Adventures
Experience Portland's renowned food scene with guided tastings at 3-5 major food cart pods.
Coastal Journey: Astoria to Florence
1
Astoria
Explore Oregon's oldest city with lunch at Bridgewater Bistro and visits to either the Heritage Museum or Maritime Museum.
2
Lewis & Clark National Historical Park
Step back in time at Fort Clatsop, where the Corps of Discovery wintered in 1805-06.
3
Seaside
Stroll the historic Promenade, visit the Seaside Aquarium, and enjoy beachfront accommodations.
4
Tillamook & Cape Perpetua
Sample famous cheese and ice cream before experiencing dramatic coastal formations.
5
Florence
End your coastal journey at Three Rivers Casino Resort after visiting the iconic Heceta Head Lighthouse.
Redwood National & State Parks
Two Nights in Crescent City
Spend two full days immersed in the majesty of the world's tallest trees. Your oceanfront accommodations at either Ocean Front Lodge or Lighthouse Inn provide the perfect base for exploring these ancient giants.
Full-day exploration of Redwood National & State Parks with options including Jedediah Smith, Lady Bird Johnson Grove, and Fern Canyon
Ranger-led talks providing insight into these ancient ecosystems. Picnic lunches amid towering giants and photography opportunities
Cultural Immersion: Ashland & Shakespeare
Spend two nights in charming Ashland, home to the renowned Oregon Shakespeare Festival. Choose your own adventure with flexible activity options:
Theatre Lovers
Behind-the-scenes Oregon Shakespeare Festival tour and optional matinee performance
Wine Wanderers
Mini wine walk with tastings at local vineyards including Weisinger and Irvine & Roberts
Art & Wellness
Gallery walks, Ashland Art Center visits, or light spa options for relaxation
Nature Seekers
Guided walks through beautiful Lithia Park or along the Bear Creek Greenway
Natural Wonders: Crater Lake to Bend
Crater Lake National Park
Marvel at America's deepest lake with its intense blue waters. Enjoy ranger presentations at Rim Village, lunch with spectacular views, and optional walks along the rim.
  • Scenic drive through Rogue River & Union Creek
  • Panoramic viewpoints perfect for photography
  • Optional hikes for various activity levels
Bend & High Desert
Experience Central Oregon's volcanic landscape and vibrant culture in Bend. Explore Newberry Volcanic National Monument or the scenic Deschutes River before enjoying dinner in this outdoor paradise.
  • Lava Butte shuttle & overlook
  • Free time in Bend's Old Mill District
  • Evening shuttle service to downtown dining
Grand Finale
Mount Hood & Columbia River Gorge
Your journey culminates with Oregon's most iconic landscapes as you travel from Bend to Portland via Mount Hood and the Columbia River Gorge.
Mount Hood & Timberline Lodge
Visit this National Historic Landmark with sweeping alpine views and optional short walks on the Pacific Crest Trail.
Columbia River Gorge Waterfalls
Experience the dramatic beauty of Vista House, Latourell Falls, Multnomah Falls, and Horsetail Falls along the Historic Columbia River Highway.
Portland Farewell
Conclude your journey with a delightful river cruise on the Willamette River. For those with later flights or staying on, enjoy a visit to the famous Powell's City of Books.
Practical Travel Information
Group Experience
Best in Class Guest to Guide ratio: Maximum 40 travelers ensures personal attention and flexibility. Groups over 25 include two expert guides for enhanced support and local knowledge.
  • Respectful seat rotation policy
  • Multiple rest stops and photo opportunities
  • Comfortable motorcoach with large viewing windows
Activity Level
Gentle to Moderate: Most walks are optional and on paved paths or well-maintained boardwalks. Perfect for active adults who appreciate comfort without sacrificing adventure.
  • Flexible participation in optional activities
  • Rest opportunities at each location
  • Accessible viewing points prioritized
What's Included
  • All listed accommodations
  • Specified meals and guided excursions
  • Park entrance fees and permits
  • Motorcoach transportation
  • Airfare transfers (within allowable window)
  • Gratuities for included services
What's Not Included
  • International or domestic airfare
  • Comprehensive travel insurance
  • Personal expenses and shopping
  • Meals marked "on your own"
  • Optional excursions not listed
  • Alcoholic beverages (unless specified)
  • Guide and Driver Tips (prepay option outlined in contract)

Important Travel Requirements: Coastal weather changes rapidly—pack layered clothing. A layer of rain gear is always advisable when traveling in the Pacific Northwest. Umbrellas will be available for use during the journey.
Your Adventure Awaits
Stunning Nature
Crashing waves, beachcombing, redwoods and pristine lakes.
Culture & Exploration
Wine, art, entertainment and museums.
Expert Guidance
Fully guided with local experts and comfortable pace

RESERVE NOW: You can secure your spot with a $25 deposit by clicking the "Reserve Your Spot Today" button below → Fill out the traveler information form and we'll send you the link to make your deposit and secure your spot . Please note that our payment processing and billing is handled by Let Go Coco, LLC. 50% of program cost due 30 days after reserving your spot and the balance due 90 days prior to departure. click the "Cancellation Policy" button below to learn more about cancellation and refunds.
Additional Details
We believe the best journeys balance careful planning with the flexibility to embrace unexpected moments. Our itineraries represent our commitment to delivering extraordinary experiences, while maintaining the adaptability that makes travel memorable and stress-free.
Important Note: Hotels, restaurants, and excursions may be substituted due to seasonal conditions or availability. All substitutions maintain equal or higher quality to ensure journey integrity.
Your Support Team Awaits
Guest Services
(833) 785-8687
Email Support
Questions Before You Travel?
Our dedicated guest services team understands that planning your dream Pacific Northwest adventure involves many considerations. Whether you need clarification on packing recommendations, want to discuss dietary requirements, or have questions about optional activities, we're here to ensure your journey exceeds expectations.
From the moment you reserve your spot until you return home with unforgettable memories, consider us your trusted travel partners. We're passionate about sharing the legends, landscapes, and coastal charms of the Pacific Northwest, and nothing brings us greater joy than helping fellow travelers discover these extraordinary places.
Meet Our Core Team
Daphne D.
Lead Guide
Program Development and Cultural Lead
Experience working with Globus, Roads Scholar and many more. Professional Photographer and program builder. Pictured here on a photography tour in the American Southwest.
Dalton M.
Lead Guide
Safety, Transportation and Active Adventures
Formerly lead archery guide at a Forbes Luxury Ranch Resort and multi-state fishing guide. 6th generation Montanan and devoted girl dad. Pictured here fishing with his daughter.
Laura O.
Operations
Back office team lead
Fractional executive specializing in small to medium-sized businesses. Born in Montana, living in Oregon, traveling everywhere! Pictured here (center) at a weaving village in Thailand.