Portland, Oregon to Anaheim in December

I am hoping to finally make our California Road trip, which was delayed from 2018 to 2020 and then again to 2022. Due to Covid my daughter will probably be making up missed college classes during the summer, so our trip will be early December. Below is our tentative schedule. Each of us chose at least one place that we must do. Any suggestions or advice would be appreciated.

Tentative Schedule:

Day 1: Fly into Oregon
Day 2: Oregon to Calif via

• Arch Rock Viewpoint / Samuel H. Boardman State Scenic Corridor, OR
• Newton B. Drury Scenic Parkway, CA
• haven't decided where to stay

Day 3:

1. Trees of Mystery, Klamath, CA
2. Lady Bird Johnson Grove in Redwood National and State Parks
3. haven't decided where to stay

Day 4: Eureka California

• Sequoia Park Zoo: (Redwood Sky Walk; Sequoia Park Forest & Gardens)
• OR Humboldt Bay Nat’l Wildlife Refuge
• and probably Old Town Eureka & Waterfront (thinking probably dinner here)

Day 5: Eureka to San Francisco via Avenue of the Giants
Days 6 & 7: San Francisco

• Alcatraz
• Pier 39
• maybe a whale watching tour?
• still researching other things, but may just wing it
  

Day 8 San Francisco to Monterey via PCH (any stops we should make?)

Day 9 & 10 Monterey

• Aquarium
• maybe a whale watching tour?
• still researching other things, but may decide when we get there

Day 11 Monterey to Anaheim

• Not via the coast; a route that is faster but maybe with a nice place to stop for lunch

DAY 12-14 Disney
Day 15 Fly Home

You’ll probably need reservations way ahead of time for Alcatraz.

Whale watching is great but can be chilly. Dress accordingly

The aquarium is pretty cool; it could take hours. Within walking distance is a big ghiradellie chocolate and ice cream shop.

I would drive the PCH at least several miles past Monterey. The views are spectacular, especially crossing those bridges!

It might be a typo but the Newton B Drury parkway is past Klamath and the Mystery tree so the order should be reversed to visit the Parkway the next day. Your first day on the road is a long one with the slow going coastal route and maybe stopping around Brookings would be better and then sight see the next day down to the Klamath/Orick area. I agree that booking Alcatraz in advance is advised but book tickets through the NPS service as it's the only official ticket office.

Monterey to Anaheim is a long drive and even using the fastest route probably pops you into the greater LA area during rush hour. It might make more sense to drive that route over two days and exit I-5 to US 101 at Paso Robles and again at Camarillo, CA, down to Rt 1 for the drive to Santa Monica, from where you can work your way back to the freeways (probably I-405, but sometimes you are better off staying on Rt. 1 past LAX and hop the I-105 or south of there to the 405) to Anaheim.

Where in Oregon are you planning to fly into? Trying to get from Portland all the way down the coast into California would be a pretty long day on the road, especially if you want to see things along the way. Even if you went a good chunk of the way down I-5 before cutting over, that still would be a full day.

Personally, I'd rework days 8-10 a bit. It's only a couple hours from SF to Monterey, and I don't think you need almost 3 full days in Monterey. Instead, I'd spend days 8-9 getting to and exploring Monterey, they spend day 10 driving down the coast to around San Luis Obispo. That will give you a chance to explore what is many people's favorite part of the coast, and will cut down on your day 11, that will go through LA to Anaheim.

I agree with Michael that Portland to CA on coast in a day would be ambitious. Google maps says Arch Rock is 6 1/2 hrs from Portland if you take I-5 to Corvallis and come out at coast at Newport. Going to coast at Tillamook only adds 30 min, but note that these times don't even include stops for gas.

I took 101 from SF Bay Area to Reedsport, OR last Fall, then followed Umpqua River to Crater Lake. We had some rain along coast even though it was only late Sept. Expect more rain and colder temps in Dec. Some recommendations around Coos Bay are Fisherman's Seafood Market (may be closed in Dec.) on docks next to boardwalk and Shore Acres and Cape Arago State Parks which are SW of Coos Bay and a little out of the way, but you can return to 101 S of Coos Bay via Seven Devils Rd from Charleston, where there are also some seafood restaurants and purveyors.

If you take Newton B Drury parkway in Prairie Creek Redwoods, you may want to take hike to coast through Fern Canyon. In SF be careful parking with any luggage (or anything that identifies you as a tourist) visible, especially at tourist spots as there are a lot of break-ins. Monterey is probably better for whale watching tour as going out Golden Gate can be rough, but even an AM trip there would probably tire you out for most of the day.

Some recommendation along coast S of SF:
Pacifica - Colombo's Delicatessen for focaccia and sandwiches
Nick's Rockaway, iconic coastal restaurant with expensive grilled crab sandwich
Pillar Point Harbor, N end of Half Moon Bay - Seafood including fresh Dungeness crab in Dec.
Sam's Chowder House is along CA-1 just S of here and always seems to have a crowd
Half Moon Bay 'downtown' has a great bakery for focaccia, bread and breakfast items
Pescadero - Duarte's famous for artichoke soup and berry pies
Santa Cruz - Turn right off CA-1 at N end of town and drive or walk West Cliff Drive from Natural Bridges to Lighthouse Point where Steamers Lane is located. Could continue to Boardwalk (probably closed in Dec) or go through Downtown.
Capitola - Gayles Bakery and/or get a slice at Pizza My Heart and eat it on bench or wall overlooking beach
Moss Landing where they also have whale watching- Phil's Fish Market is highly recommended

Monterey has a great Aquarium which is also on bayfront hike that starts near the harbor and goes for a few miles to and past Lovers Point. Downtown, the Mission and beach in Carmel-by-the-Sea are also worth a visit. There are many wine tasting rooms and The Cheese Shop in Carmel Plaza is great.

From Monterey the quickest route to LA would be CA-68 towards Salinas and take River Rd to join 101 at Chualar. If you continue on River Rd there are some wineries and then there are literally 100s of them around Paso Robles. The shortest route to LA from there is CA-46 to I-5, but 101 is much more scenic and not much longer although there always seems to be traffic getting past and S of Santa Barbara. 101 also gives you option of taking CA-1 past Malibu. If you take CA-1, Splash Cafe in Pismo Beach is famous for chowder.

I always try to proofread, but see I had a typo/error in my last sentence that I'm too late to edit.

I meant to say "If you take US-101 (when going S from Paso Robles to LA), Splash Cafe in Pismo Beach is famous for chowder.

Pismo also is often the first place along coast (along with even more protected Avila Beach) where weather is more like SoCal than Northern CA. Good pier and beach for taking a walk.

Thank you for all your comments. I finally had some time to sit down and look at all of them and do some Googling. We had to make some changes due to my daughter’s school schedule and had to cut a day off our trip. I also made a few changes to the itinerary based on comments and am still looking into some of the suggestions. As of now, out trip looks like this:

DAY 1:
Fly into Portland, Oregon. Stay overnight.

DAY 2:
Portland to Brookings, OR; via Samuel H. Boardman State Scenic Corridor stopping at Arch Rock Viewpoint & Picnic Area & possibly other places along the way. We will take a partially coastal route

* ≈ 6 hours travel time from hotel before tops; so we expect/hope 8-to-9-hour ride total

DAY 3
Brookings, OR to Trees of Mystery, Klamath, CA and on to Eureka, CA

After Trees of Mystery, drive through Redwood National & State Parks (Newton B. Drury Scenic Parkway)

other stops will depend on how long we stay at trees of Mystery, but may include
* Lady Bird Johnson Grove Trail to see the albino redwood (assuming the droughts haven’t killed it)
* hike to coast through Fern Canyon.

DAY 4
Eureka California
* Skywalk at the Sequoia Park Zoo (most likely activity)
* Sequoia Park Forest & Garden (possibly)
*Humboldt Bay National Wildlife Refuge (possibly)
*and Dinner in Old Town Eureka & Waterfront

DAY 5 Eureka to San Francisco Via Humboldt Redwoods State Park & Avenue of the Giants
* Stops at California Federation of Women’s Clubs Grove & Shrine Drive-Through Tree
* Dinner in San Francisco Restaurant if we are energetic enough
* Approx. 4.5 hour drive time (before stops)

DAYS 6 & 7
San Francisco
• Alcatraz
• Pier 39/Sea Lions
• Fishermen’s Wharf
• Golden Gate Park
• Presideo
• Ride a Cable Car

DAY 8:
San Francisco Monterey
Drive down the coast on PCH. Go Past Monterey for a bit before checking into the hotel.

DAY 9: Monterey
* Monterey Aquarium ?
* Whale Watching Tour?

DAY 10: Monterey to Anaheim
Stop at Pismo Beach along the way?

DAY 11-13: Disneyland
Day 14 Fly home

You have a nice trip coming together !! I would recommend driving through Prairie creek redwoods SP on the Newton B Drury parkway, it's a small diversion that hardly adds any time but a lovely drive. The same goes for 'The Avenue of the giants' in Humboldt Redwoods SP. I also recommend you book your Alcatraz tickets in advance through the NPS official page.