Oregon is an amazing state and the best way to see some of its hidden gems is to take a road trip. Along the way, you will be greeted with waterfalls, caves, shimmering lakes, beautiful beaches, towering Redwood trees, and more. 
Buckle your seatbelt because you are about to do some serious driving. I recommend renting a Chrystler Pacific for the trip. It’s by far the most spacious minivan allowing you and your family more room. Also a good rental option would be a Dodge Durango that seats seven.
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9 Day Southern Oregon Itinerary
I’m assuming that you are flying into Oregon to make this trip, therefore I’ve got the Portland Airport as the starting point. You can adjust your starting point accordingly if this doesn’t work for you. The whole itinerary can be tweaked to suit your needs and the amount of time you have to travel.
Day 1: Drive from Portland to Steamboat Inn
It’s almost a four-hour drive from the Portland airport to Steamboat Inn. If you hit five o’clock traffic you can expect it to take five hours. There is an In N Out along the way near Salem if you get hungry. In Eugene, there’s a Sonic. However, if you can hold off eating until you get to Steamboat Inn. The food will totally wow you.
Check-in into Steamboat Inn:
Perched on a bluff with a commanding view of the North Umpqua River, Steamboat Inn offers beautiful accommodations, fine dining, local wines, exquisite gardens, and a tackle and gift shop. Located on Hwy 138 in the middle of 31 miles of “fly-fishing only” water on the North Umpqua River it is a destination in itself. Steamboat is also the perfect place to stay while exploring all the area has to offer including loads of waterfalls.
Dinner at Steamboat Inn: By the time you have gotten to Steamboat Inn you are basically in the middle of nowhere so you will be eating your meals here. If you rent a cottage you will have a kitchen and can prepare your own meals.
They have a wonderful kitchen that creates amazing breakfast and dinners. The menu is full of Steamboat Traditions and the daily specials feature fresh local products. Don’t forget to save room for our house-made desserts. If you are planning a fishing or sightseeing trip. Just order from the front desk by 8 pm the evening before. Espresso is available in the library lounge.
After dinner, grab a game or two in their library to take back to your room and play with your family. There’s basically no internet and no TV so it’s a great opportunity to spend quality time with the people you are traveling with. 
Day 2: Flyfishing and Waterfalls
Breakfast: Kick-off your morning with a delightful breakfast at Steamboat Inn followed by a day of hiking the waterfalls in the Umpqua National Forest. Before you head out hiking don’t forget to pick up your sack lunch from the hotel. They have great sack lunch choices available in the morning.
Flyfishing: You can fish the North Umpqua the year around for steelhead, but do not do this without a guide if you have never fished here before. The rivers in Oregon are fierce. Never get in an Oregon river without doing your research first. You can get your fishing license online here.
- Ty Holloway – hollowaybrosfishing.com 541-729-0692
- Steelhead Water – www.steelheadwater.com Rich Zellman 541-890-7084
- Renton’s River Adventures – www.gourmetflyfishing.com Dillon Renton 541-480-8067
Waterfall Highway: Oregon has it’s very own waterfall highway. As you drive Highway 138 there will be one waterfall after another, ask the front desk for a free map. Some are quick and easy hikes, while others are a bit more difficult. In half a day you will have time to do two short hikes and one longer one.
- Toketee Falls – off Highway 138, this is one of Oregon’s most famous waterfalls renowned for its columnar basalt formation framing the two-stepped falls. Toketee Falls drops 113 feet, which includes a 28-foot upper-tier plunging into a pool flanked by a deep alcove, and then an 85-foot plunge into a large pool.
- Clearwater Falls – Off Highway 138. Unlike most waterfalls, this one appears to be springing out from beneath the green, moss-covered rocks and thousands of intertwined tree roots. On Clearwater Creek
- Fall Creek Falls – off Highway 138, the Falls Creek Falls Trail features two waterfalls. The first is an 80-foot drop, and 100 feet downstream is the lower 40-foot falls.
- Whitehorse Falls – 40 miles from Union Creek off Highway 138. Also on Clearwater Creek, Whitehorse Falls comes out of a narrow trough and tumbles 14 feet over a wall into a large pool down below.
- Watson Falls – Off Highway 138 is the third highest waterfall in Oregon, Watson Falls. It is a majestic sight with water cascading 272 feet over basalt lava cliffs – and you can walk under the falls. Located in the Umpqua National Forest, 47 miles from Union Creek, the trail is an easy .6 miles.
Day 3: Drive to Crater Lake
This morning after you check out of the Steamboat Inn head towards Crater Lake, an 88-mile drive. You will be going along highway 138 again, so if you missed out on one of the waterfalls you wanted to see now is the time to stop at it. If you drive it straight with no stops it should take you 3 hours.
Depart for Crater Lake National Park
Driving to Crater Lake can be challenging at times. Due to heavy snowfall, some of the entrances may be closed. The last time we visited two entrances were closed, this was during Memorial Weekend in late May. This added about two hours of driving on to our trip. So keep this in mind.
Depending on which way you drive, we have a few suggested stops to make.
- Natural Bridge in Prospect, OR, US, 97536
- Rogue River Gorge Viewpoint, located at 56541 Rogue-Umpqua Scenic Byway, Prospect, OR, US, 97536
Crater Lake
Crater Lake is Oregon’s shimmering blue gem. It’s a must-see landmark during any trip to Southern Oregon. There are two ways many people enjoy the lake. One way is to drive the 33-mile Rim Drive and stop at the many vista points overlooking the water if the road is open. The other is to make the one-mile hike down a switchback trail to the water’s edge again only if the trail is open.
Visitors can swim, fish, take a boat tour, or just eat a trail lunch on the shores of Crater Lake. Crater Lake National Park rangers are on hand to explain the eruption of Mt. Mazama about 7,700 years ago and how the mountain collapsed, creating a 2,000-foot deep crater. The end result is a lake created solely from snowmelt–there is no river flowing in. Scientists have measured the water ’s clarity to as deep as 120 feet.
Tonight stay the night at Crater Lake Lodge. They have 71 rooms overlooking the lake at Rim Village. It is typically open May 15 through October 11. Rooms begin at $200 per night. Reservations can be made up to 365 days in advance either online or by calling 866-292-6720. I highly recommend making your reservation as far in advance as you can.
At the southern entrance of Crater Lake there is a Tesla Super Charger.
Day 4: Head to Klamath Falls
Drive from Crater Lake to Running Y Ranch Resort located at 5500 Running Y Road Klamath Falls, OR 97601.
Check-in at Running Y Ranch Resort: Inspired by the outdoors and bathed in the glow of 300 days of sunshine, Running Y Ranch Resort invites you to embark on the adventure of a lifetime. Situated at the foothills of the Cascade Mountain Range on 3,600 pristine acres, our Klamath Falls resort is surrounded by endless natural wonders. They have several charging stations in their parking lot of electric or hybrid vehicles. 
Dinner in Klamath Falls: There are lots of good places to eat in Klamath Falls. Some of our favorites include Klamath Basin Brewing Co., Rodeos Pizza, Saladeria, and Ruddy Duck. Fun fact, Noah and I live in Klamath Falls when he was two! I always thought the best part of living here was the food.
Day 5: Ziplining
Breakfast: Have breakfast at the Running Y.
Check out of Running Y Ranch Resort and drive out to Crater Lake Zipline located at 29840 OR-140, Klamath Falls, OR 97601.
Crater Lake Zipline: You will fly high ion 9 ziplines at heights of up to 100 feet in the trees, traverse two sky bridges, and conquer up to two controlled rappels! Crater Lake ZipLine participants ages 10 and up zip from tree to tree with two trained guides handling the gear and transfers.
They use state-of-the-art equipment and all tours include a ground school training session facilitated by the guides at the beginning of the tour. Participants learn to hand brake, (participants use their hands with a special glove to slow and brake themselves) sit in their harness, and other techniques needed for zipping. You will be here for about 2.5 to 3.5 hours.
After zip lining drive to Grants Pass.
Lunch: You will pass an In N Out along the way. If you do not want In n Out, there are a lot of places to eat in Medford.
Check-in at Redwood Hyperion Suites: The Redwood Hyperion Suites are tucked among towering trees, tranquil water features, and award-winning gardens, in the heart of Grants Pass, Oregon and boasts a diverse variety of comfortable hotel rooms and suites to accommodate the most discriminating of guests.
Afternoon: You have the whole afternoon and early evening to explore Grants Pass. One extremely popular activity is going down the river in a jet boat.
Dinner: Tonight have dinner at Taprock Northwest Grill located at 971 SE 6th St, Grants Pass, OR 97526.
Taprock Northwest Grill
If there is good weather a firework show begins at 9:00 p.m. along the river and the restaurant offers great views. The restaurant will get very busy the closer it gets to the show, try to arrive early enough to get a table on one of the decks.
Day 6: Caves and Treehouses
Check out at Redwood Hyperion Suites and head to Oregon Caves National Monument.
When you arrive at Oregon Caves National Monument head inside and sign up for the Oregon Caves Guided Tour right away. Expect to have to wait a bit. 
The Oregon Caves are one of only five national parks or monuments in Oregon. The 480-acre Oregon Caves National Monument, located in the Siskiyou Mountains at elevations from 3,800 to 5,460 feet, was created in 1909. Temperatures in the caves hover around 42 degrees Fahrenheit year-round. The caves are home to one of the largest, most pristine, and most complete segments of old oceanic crust in Western America.
Once you are done at the Oregon Caves, head to Out N About Treehouse Resort. 
Tonight stay the night at the Out n About Treehouse Treesort. You will need to make reservations way in advance to stay here. It’s a really neat place and as you’ve already guessed, you stay in a tree house. How fun is that? It is definitely a splurge to stay here, but it’s worth the extra money, especially if you are traveling with children, because it’s a one of a kind experience.
Day 7: Horseback Riding and Redwood Trees
After breakfast, head out for a trail ride if you like. They also have zip lining available at the Tree House Resort.
Today you’ve got a big decision to make. You can wrap up your trip or you can cross into California and visit the Redwood National Forest then head back into Oregon along the coast.
I am going to assume you’ve made the right decision and you’re headed down into Cali to experience a little bit of the Redwood National Forest.
As you drive down you will have the opportunity to get onto Howland Hill Road, which is noted on the map. This is an unpaved trail that will take you through some giant trees. It’s not a great road, but I took a Chrystler Pacific down it and it was fine!
When you get to the end of the trail you basically pop out in Crescent City which is a bit out of the way, but an ideal spot to have some lunch while overlooking the ocean. If you are driving a Tesla know that there is a supercharge station here.
Lunch: Plan to have lunch in Crescent City. We recommend eating at Schmidt’s House of Jambalaya. There you can sit outside and stare at the ocean while you eat!
After lunch proceed north. You are now headed back into Oregon to Bandon, a cute little beach town along the coast. There’s lots of AirBNB places to stay as well as a Best Western on the beach.
Day 8 – Beach Day!
Morning: Take a windsurfing or a kiteboarding class at Flora’s Lake Windsurfing & Kiteboarding. Floras Lake Windsurfing is located at 92870 Boice Cope Road, Langlois, OR 97450 and their phone number is 541-348-9912.
Lunch: After your lesson head to Tony’s Crab Shack for lunch.
Afternoon: You’ve got two options for this afternoon. Enjoy a round of golf at Bandon Dunes golf resort or head out for horseback riding on the beach.
Bandon Dunes Golf Resort located at 57744 Round Lake Drive, Bandon, OR 97411. Phone: 541-347-4380
Bandon Beach Riding Stables located at 54629 Beach Loop Rd, Bandon, OR 97411. Phone: 541-347-3423
Dinner: Have dinner at Broken Anchor Bar and Grill or Asian Garden. Both are excellent.
Day 9 – Head Home
Okay, that’s a wrap y’all. You’ve just completed an epic road trip that will have you reminiscing for many years to come. You will think back on all those glorious waterfall hikes, the majestic Crater Lake, the cool places you stayed, the towering trees, and those beautiful beach views.
On your way home there are lots of other places to stop. You could continue along 101 towards Newport or cut over to I5 and go through Eugene and Salem. If you are looking for places to stop in any of these places check out these posts.
17 Fun Things to do in Salem, Oregon with Kids
Top 12 Family Friendly Things to do in Eugene Oregon
