Oregon Explorer 2025
Enjoy the perfect blend of adventure and relaxation as you see some of the very best Oregon has to offer.
TRIP DATES:
All 2025 trip dates are SOLD OUT!
Trip Length
6 Days
$2295 Per Person
Explore the very best Oregon has to offer – from the deepest lake in the United States to the tallest peak in Oregon and the valleys in between, you’ll find the perfect blend of relaxation and adventure on our Oregon trip.
Activities
- Hiking
- Touring
- Canoeing
- Wine Tasting
Included
- Three nights camping at Crane Prairie Campground
- Two nights at Jupiter Hotel NEXT – double occupancy
- Crater Lake National Park Day Tour
- Columbia River Gorge + Mount Hood Day Tour
- Willamette River Valley Wine Tour (tastings not included)
- Stargaze Canoeing Tour
- All transfers
- Group camping equipment
- Meals as outlined below
- Two medically-trained, naturalist guides
Not Included
- Gratuity for your guides
- Tastings at the wineries
- Meals not outlined below
- Any souvenirs
- Flights to and from Portland
Weather
Weather tends to be quite mild this time of year. Be sure to pack sun protection, rain gear, and layers!
Intensity- Mild to Moderate
This trip is great for all ability types. Your guide will help select the best trails for our group during our two days of hiking. There will be plenty of time for relaxation as you tour Oregon’s wine country and the beautiful cities of Bend and Portland.
Accommodations
- Three nights camping at a National Forest Service campground.
- Two nights at a three-star hotel in downtown Portland
Flights
Please plan to arrive at Portland International Airport by 1:00 PM PST on Day 1. Your guide will pick you up shortly after arrival. Alternatively, your guide can collect you from your accommodation or another central point in Portland (within 30 minutes of the airport) by 1:00 PM PST if you choose to arrive a day early.
Your guide will transport the group to the airport to arrive by 12:00 PM PST on Day 6. Please plan a departure after that time. Alternatively, if you’d prefer to book a hotel, please be prepared to find personal transportation to the airport (via Lyft, taxi, etc).
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Day One
Get ready for an adventure! Your guide will pick you up by 1pm at Portland International Airport. From Portland, you’ll make the beautiful ~3.5 hour drive to La Pine where you’ll be camping for the next three nights. We’ll all set up camp together and your guides will make you a delicious campfire meal. We’ll get to know each other and get ready for a fun-filled week ahead.
Meals: D
Day Two
Today you’ll head ~2 hours south to Crater Lake National Park – the deepest lake in the United States! Your naturalist guide will teach you all about the history and geological wonder that is Crater Lake and the surrounding Cascade Mountains. Your group will hike and explore this natural wonder before heading back to camp for the evening.
Meals: B, L, D
Day Three
Take it a bit easier today with a slower start! Then, you’ll make the 30 minute drive to Bend where you’ll enjoy lunch (not included) at a local restaurant or brewery. Tonight, get ready for a special treat as you peer up at the night sky from your canoe. The group will go stargaze canoeing and hear about the constellations as you quietly drift around a beautiful Cascade lake.
Meals: B, D
Day Four
It’s time to say goodbye to central Oregon as you pack up and leave camp. You’ll make the ~3.5-hour drive to Portland, stopping in the Willamette Valley for a wine-tasting tour (tastings not included). You’ll love the world-famous Oregon pinots! Tonight, you’ll explore the city of Portland before stopping to sample the local cuisine at some food trucks.
Meals: B, L
Day Five
Head east along the Columbia River Gorge for your final day of touring! Your naturalist guide will explain the area’s geological wonders while stopping to chase beautiful waterfalls and catch views of the nearby Cascade peaks. Once back in Portland, you’ll have your final farewell dinner together (not included).
Meals: B, L
Day Six
It’s time to say goodbye to Oregon for now with memories and new friends! Your guide will drop you off at the airport by 12 pm PT.
Meals: B
Packing LIst
Required Gear
- Day pack (15-30 liters recommended)
- Luggage (can be left in the vehicle, 1 small suitcase per person)
- Sleeping bag (also available to rent), rated to 20 degrees or below
- Pack cover
- Headlamp
- Reusable water bottles or bladders (3L total capacity)
Recommended Gear & Personal Items
- Hiking poles
- Cotton or silk sleeping bag liner (optional, recommended if renting)
- Travel pillow
- Sunscreen
- Earplugs
- Insect repellent
- Toiletries (please choose biodegradable and scent-free items)
- Small, personal first aid kit (including blister treatment)
- Small, quick dry towel
Required Clothing
- Warm jacket (down, puffy, fleece)
- Rain jacket or shell
- Rain pants
- Breathable wicking base layers
- Lightweight hiking pants
- Warm clothes to sleep in
- Warm hat
- Gloves
- Sun hat with a brim
- Wool socks (1 pair per day of trip)
- Hiking boots
- Sunglasses
Recommended Clothing
- Buff or neck scarf
- Comfortable clothes for camp
- Sandals or camp shoes
- Rain pants
Trip FAQ’s
What will we eat?
Meals may be prepared by guides, picked up as boxed lunches, or enjoyed in restaurants. We prioritize seasonal, fresh ingredients and local suppliers in all regions. We can cater to most dietary requests and allergies with advanced notice. Be sure to include this information in our client intake form when registering for your trip!
Who else will be there?
Good Trippers can be any age and everyone is welcome!
We get families, couples and friends, but most of our travelers come solo! We have hiking trips for all abilities, just make sure to review the Intensity section for information about what to expect on your trip. All group multi-day trips are 18+. If you’re traveling with kids, we’d be happy to make any itinerary private! Email info@goodtripadventures.com.
Do you offer payment plans?
We are here to help! We offer flexible payment plans tailored to your needs. Reach out to us for more information on how we can assist you with payment options. Regardless of the payment plan implemented, full payment must be received by 30 days in advance of the trip start.
Are there age requirements?
They say age is just a number and we (mostly) agree! However, due to legal restrictions and group dynamic considerations, we do have a minimum age of 18 on our public group departures. But there’s no maximum!
If you have someone under 18 in your group, we can accommodate all ages on a private adventure, so let’s talk!