Legends, Landscapes & Coastal Charms: 11-Day Oregon and Redwoods Discovery Tour Details
June 4 - 14, 2025
Embark on an unforgettable journey through the Pacific Northwest with Small Town Journeys. Our meticulously crafted 11-day adventure showcases Oregon's diverse landscapes, from Portland's urban charm to the majestic Redwoods and the awe-inspiring Crater Lake. Perfect for freedom travelers seeking both structure and flexibility.
Tour Highlights & Pricing
What's Included
  • 10 nights accommodation in carefully selected hotels
  • 9 breakfasts, 8 lunches, 5 dinners, and a farewell river cruise brunch
  • 2 experienced guides for groups of over 25
  • All entry fees for daily activities, entertainment and excursions
  • Optional upgrade activities available for an additional fee
  • Comfortable transportation throughout the journey
Pricing
Double-occupancy: $3,950 per person (paid by check or EFT bank draft)
Credit card payment: $4,068 per person (double-occupancy)
Single supplement: $750 ($772 if paying by credit card)

This tour runs Thursday, June 4 - Sunday, June 14. Limited spots - book early to secure your place!
Detailed Itinerary: Days 1-3
Day 1: Arrival in Portland
Mileage: 10-15 miles | Travel Time: 30-45 mins
  • Airport pickup & transfer to boutique Inn at Northrup Station
  • Welcome dinner featuring Portland's famous food carts
  • Optional evening walk on trendy NW 23rd or Trolley Car Tour
Settle into Portland's vibrant atmosphere with a progressive dinner through the city's renowned food cart pods, sampling 4-6 small plate tastings while learning about the local culinary scene.
Day 2: Portland to Seaside
Mileage: ~118 miles | Travel Time: ~2.5 hours
  • Scenic drive via Hwy 30 to Astoria for lunch at Bridgewater Bistro
  • Visit Heritage Museum or optional upgrade to Maritime Museum
  • Explore Lewis and Clark National Historic Park
  • Evening stroll on the Seaside promenade with dinner on your own
Follow the Columbia River through historic mill towns to Astoria, where you'll enjoy fresh local seafood with river views before immersing yourself in the region's rich history.
Day 3: Seaside to Florence
Mileage: ~160 miles | Travel Time: ~4-5 hours
  • Drive south on Hwy 101 along the stunning Oregon Coast
  • Visit Tillamook Creamery for cheese production tour and tastings
  • Explore Cape Perpetua Scenic Area with ranger-led interpretation
  • Photo stop at iconic Heceta Head Lighthouse
  • Evening at Three Rivers Casino Resort with dining options
Experience Oregon's breathtaking coastline with stops at local landmarks, from the famous Tillamook cheese factory to dramatic coastal formations and a historic lighthouse perched on a scenic bluff.
Detailed Itinerary: Days 4-6
Day 4: Florence to Crescent City, CA
Mileage: ~185 miles | Travel Time: ~5 hours
  • Drive Oregon's southern coast with scenic stops
  • Visit Shore Acres State Park, Bandon, and the Prehistoric Gardens
  • Cross into California late afternoon
  • Check in at oceanfront accommodations in Crescent City
Continue your coastal journey south, crossing into California where the rugged coastline meets the beginning of redwood country, with your comfortable oceanfront lodging providing the perfect base for exploration.
Day 5: Redwoods Immersion Day
Mileage: ~50-60 miles | Travel Time: 1.5-2 hours + hiking
  • Full day exploring Redwood National & State Parks
  • Options include Jedediah Smith, Lady Bird Johnson Grove, and Fern Canyon
  • Picnic lunch amid ancient trees
  • Ranger-led talk or photography walk
Stand in awe among the world's tallest trees in this immersive day dedicated to the majestic redwood forests, with expert guidance to enhance your understanding of these ancient ecosystems.
Day 6: Crescent City to Ashland
Mileage: ~155 miles | Travel Time: ~3.5-4.5 hours
  • Scenic inland route via Smith River and Grants Pass
  • Group split option: Oregon Caves National Monument OR Garden & Gallery Experience
  • Continue to cultural hub of Ashland
Journey inland through river canyons with a choice of experiences - explore the fascinating underground world of Oregon Caves or enjoy the artistic charm of local gardens and galleries before arriving in Ashland, Oregon's cultural jewel.
Detailed Itinerary: Days 7-9
Day 7: Full Day in Ashland
Mileage: 10-30 miles | Travel Time: <1 hour
  • Morning cultural kickoff with Oregon Shakespeare Festival campus tour or Lithia Park walk
  • Group lunch at Louie's of Ashland overlooking Ashland Creek
  • Afternoon choose-your-own-adventure: theatre, wine tasting, art galleries, or nature walks
  • Free time to explore downtown shops
  • Dinner on your own at recommended local restaurants
Immerse yourself in Ashland's rich cultural offerings with flexible options to match your interests, from world-class theatre to local wineries, all within this walkable artistic community.
Day 8: Ashland to Crater Lake
Mileage: ~110 miles | Travel Time: ~2.5-3 hours
  • Scenic drive through Rogue River & Union Creek
  • Visit Crater Lake Rim Village with ranger presentation
  • Lunch with spectacular lake views
  • Optional walks along the rim with varying difficulty levels
  • Evening at charming Union Creek Resort or historic Prospect Hotel
Witness the breathtaking beauty of America's deepest lake, formed in a collapsed volcano caldera, with its intense blue waters surrounded by steep cliffs - truly one of Oregon's most magnificent natural wonders.
Day 9: Crater Lake to Bend
Mileage: ~130 miles | Travel Time: ~2.5-3.5 hours
  • Drive through high desert landscapes on Hwy 97
  • Optional stop at Newberry Volcanic National Monument or Deschutes River
  • Afternoon arrival in Bend with free time
  • Dinner on your own with shuttle service to recommended restaurants
Transition from mountain forests to high desert as you journey to Bend, Oregon's outdoor recreation hub, with time to explore volcanic landscapes before enjoying the city's renowned dining and craft beer scene.
Detailed Itinerary: Days 10-11
Day 10: Bend to Portland
Mileage: ~190 miles | Travel Time: 5-6 hours
  • Drive through Warm Springs to Mount Hood
  • Visit historic Timberline Lodge with optional short walks
  • Columbia River Gorge waterfall tour including Vista House, Multnomah Falls, and Horsetail Falls
  • Evening arrival in downtown Portland
Experience Oregon's diverse landscapes in one spectacular day - from high desert to alpine mountain to lush gorge with thundering waterfalls, before returning to Portland for your final evening.
Day 11: Portland Departure
Mileage: 10-15 miles | Travel Time: 30-45 mins
  • Farewell brunch cruise on the Willamette River
  • Optional visit to Powell's City of Books for those with later flights
  • Airport transfers coordinated based on flight times
Conclude your journey with a delightful river cruise featuring buffet brunch and champagne toast while enjoying Portland's waterfront views, followed by convenient airport transfers or extended exploration for those with later departures.
The magnificent Multnomah Falls in the Columbia River Gorge stands at 620 feet tall, making it Oregon's tallest waterfall and one of the most photographed natural wonders in the state.
Your journey concludes with a memorable brunch cruise aboard the Portland Spirit, offering panoramic views of the city skyline and a chance to reflect on your Pacific Northwest adventure.
Accommodations Overview
We've carefully selected comfortable, well-located accommodations that showcase the character of each destination while providing all the amenities needed for a relaxing stay after each day's adventures.
Portland (Nights 1 & 10)
Inn at Northrup Station
This boutique hotel in Portland's trendy Northwest district offers colorful, spacious suites with kitchenettes, a rooftop terrace, and complimentary streetcar passes. The perfect base for exploring Portland's renowned food scene and unique neighborhoods.
Seaside (Night 2)
Best Western Plus Ocean View Resort
Located directly on the Promenade with stunning ocean views, this comfortable hotel provides easy access to Seaside's beach, shops, and restaurants. Many rooms feature private balconies overlooking the Pacific.
Florence (Night 3)
Three Rivers Casino Resort
This full-service resort offers well-appointed rooms, multiple dining options, entertainment, and a convenient location for exploring the central Oregon coast.
Crescent City (Nights 4-5)
Oceanfront Lodge or Lighthouse Inn
Enjoy oceanfront accommodations with breathtaking views of the rugged Northern California coastline, providing the perfect base for exploring the magnificent Redwood forests.
Ashland (Nights 6-7)
Downtown Ashland Hotel
Stay in the heart of this cultural hub, within walking distance of the Oregon Shakespeare Festival, Lithia Park, and numerous restaurants and galleries that make Ashland special.
Crater Lake Area (Night 8)
Union Creek Resort or Prospect Historic Hotel
Experience rustic charm in these historic properties surrounded by forest, offering a peaceful retreat with easy access to Crater Lake National Park.
Bend (Night 9)
Riverhouse on the Deschutes or Downtown Hotel
Comfortable accommodations in Oregon's outdoor recreation capital, with shuttle service to downtown dining and easy access to the Deschutes River Trail.
Why Choose Small Town Journeys?
Our experienced guides bring each destination to life with local insights, historical context, and personalized attention to ensure every traveler has a meaningful experience.
The Small Town Journeys Difference
With over 15 years of experience crafting memorable Pacific Northwest adventures, we pride ourselves on creating tours that balance structure with freedom, allowing you to experience each destination authentically.
Expert Local Guides
Our knowledgeable guides share insider perspectives and hidden gems that typical tourists miss, bringing each destination to life with stories and context.
Perfect Balance of Structure & Freedom
We provide a thoughtfully planned framework with built-in flexibility, allowing you to customize portions of each day to match your interests and energy level.
Carefully Curated Experiences
From accommodations to activities, we've personally vetted every element of your journey to ensure quality, authenticity, and memorable moments.
Small Groups, Big Experiences
Our small group size allows for personalized attention, access to intimate venues, and the flexibility to adapt to weather, interests, and unexpected opportunities.
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

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.
RESERVE NOW: You can secure your spot with a $25 deposit by clicking the "Reserve Your Spot Today" button below. 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.
Reserve Your Spot Today
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 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.