FULL 14 day Itinerary for your Critique

Question

Ok, as I was saying before, family of 4 (2 adults, 2 kids (7 and 11), first time doing the below itinerary. Been on road trips before, handle it very well. Would like your input if all makes sense my redone itinerary after much thinking.

Day 1: Aug. 1 Fri

Ferry (Tsawwassen)+ ride from Victoria, BC to Seaside, OR

Beach time, arcades, shopping for trinkets and local specialties for kids, Dundee’s donuts, pig’n’pancake, maybe do one of the following if not too late: go carts, aquarium, feeding seals, renting bike to ride beach, reading deuce coupe is fun.

Overnight in Seaside

Day 2: Aug 2 Sat

Stop at Cannon Beach really early

Tillamook Creamery 10.00 am (some said skip it, but I looked photos, it seems like kids would like it?)

Evergreen Aviation (5.00 pm close)

No way that we stop at Silver Falls BUT in case museum closed or so, South Falls Loop hike for behind fall experience

Overnight in Salem

Day 3: Aug 3 Sun

Long drive, start early

Stop at Lake Shasta Caverns, didn’t book but hoping available on the spot, last tour at 4.00pm

Overnight in Redding

Day 4: Aug 4 Mon

Jelly Belly, self tour

Either stop at Sonoma/Napa for Castello di Amorosa experience with kids, waiting on your neh/yah and overnight here

Or straight to Santa Cruz for overnight via Hwy 1 with some pull outs if time permits, if not, then on the way back, a bit too much driving but it’s last push it seems

Day 5: Aug.5 Tue

Beach Boardwalk with rides

Santa Cruz Wharf with sea lions

Drive to Monterey

Overnight in Monterey

Day 6: Aug.6 Wed

Monterey explore

Cannery Row, Monterey Peninsula Recreational Trail (1 mile starch only between Aquarium and Point Lovers), Coast Guard Pier, Old Fisherman's Wharf, aquarium maybe

Overnight in Monterey

Day 7: Aug.7 Thu

drive out and back to Pfeiffer Beach with pullouts, Carmel

Overnight in Monterey

Day 8: Aug.8 Fri

Point Lobos with 3-4 trails, aquarium if didn’t fit in first day

Overnight in Monterey, a bit too many days here for my liking so trying to consolidate and do some things in between, so perhaps will cut it to 3 overnights

Day 9: Aug.9 Sat

Drive from Monterey to SF

Depending when we arrive and whether we will stop at any pullouts

Disney Discovery Centre in Milpitas, if not directly to the city through Hwy 1 with pullouts if didn’t do them on the way in

Overnight in SF

Day 10: Aug.10 Sun

Full day to explore SF

Overnight in SF

Day 11: Aug.11 Mon

Full day to explore SF

Leave to Sonoma/Napa if didn’t visit on the way in? and overnight there.

Day 12 – Day 14 drive back and either Evergreen Museum or Silver Falls depending which one didn’t visit or perhaps Avenue of the Giants, Ashland as detour, or Crater Rock Museum in Central Point, depending where stops will be will scope 2 overnights in between.

Answer

Your 14-day itinerary is very ambitious but seems well thought out for a family who enjoys road trips and sightseeing. Since you have kids aged 7 and 11, pacing and flexibility will be key to keeping everyone happy and energized. Here’s a detailed critique and suggestions by segment of your trip:

Days 1–3: Seaside, Cannon Beach, Salem, Redding

Seaside offers a classic beach town experience for kids, and the activities you’ve listed (arcades, bike rentals, pig’n’pancake, Dundee’s donuts) are very kid-friendly.
Cannon Beach early in the morning is a smart move to avoid crowds. It’s iconic and photo-worthy, especially Haystack Rock.
Tillamook Creamery can be hit or miss with kids, but the ice cream and cheese-making demos are usually a hit. Timing-wise, arriving around 10 am works well.
Evergreen Aviation is interesting for airplane enthusiasts and older kids. Closing at 5 pm is fine if you allow travel time from Tillamook.
For South Falls Loop at Silver Falls, keep in mind that if you’re tight on time or arrive late, it may be better to skip and save energy for Redding.

Day 4: Redding to Sonoma/Napa or Santa Cruz

Jelly Belly tour in Fairfield is straightforward and kid-friendly.
Castello di Amorosa is an unusual pick with kids but can be a fun “castle experience” – just note that tastings are adult-only, so plan accordingly.
If your priority is less driving stress, heading straight to Santa Cruz via Hwy 1 may be more relaxing. Pullouts along the coast provide scenic stops, and you can always enjoy the ocean views along the way.

Days 5–8: Santa Cruz and Monterey

Santa Cruz Boardwalk is classic family fun; the Wharf is also great for casual wildlife spotting.
In Monterey, splitting 3–4 days is ideal, but you may be able to consolidate to 3 nights if you want a slightly faster pace. Highlights like Cannery Row, Old Fisherman’s Wharf, Coast Guard Pier, and the recreational trail are good. Monterey Bay Aquarium is a must-do if kids enjoy marine life; reserve tickets if possible to avoid lines.
Pfeiffer Beach and Point Lobos day trips are scenic. Pullouts along Hwy 1 give great photo opportunities. Consider combining them into a single day to save a night.

Days 9–11: San Francisco and Sonoma/Napa

Driving from Monterey to SF offers options for scenic stops. Pullouts along Hwy 1 are worth it if you missed them earlier.
Disney Discovery Centre in Milpitas is kid-friendly but optional if timing is tight.
Full days in SF are smart; Union Square, Fisherman’s Wharf, Chinatown, and Golden Gate views are all achievable with public transit. Consider cable car rides and a ferry to Alcatraz if interested.
If you didn’t visit Sonoma/Napa on the way up, allocating a night there is feasible. Some wineries have kid-friendly activities, but focus on those with outdoor space.

Days 12–14: Return Drive via Northern California and Oregon

On the way back, incorporating Avenue of the Giants (redwoods), Ashland detour, or Crater Rock Museum can break up long drives. Two overnight stops in between make sense for pacing.
Check opening hours in advance, especially for museums and attractions, as some may close early in August.

General Suggestions:

Be flexible with timing; some long drives may require earlier starts than planned.
Reserve any popular attractions (like Monterey Bay Aquarium or Castello di Amorosa) in advance to avoid long waits.
Snack and hydration breaks are essential with young kids on long drives.
Consider the total number of overnights in Monterey – 3 nights might be sufficient while still allowing you to enjoy the coast and attractions.
Overall, your itinerary is realistic if your family enjoys active days. Consider a “buffer day” somewhere mid-trip in case of fatigue or unexpected delays.

In summary, your itinerary hits the major highlights and balances driving with sightseeing. Slight consolidation in Monterey and careful timing of museum stops will make the trip smoother. You have a mix of kid-friendly activities and scenic experiences, which is ideal for a first-time West Coast road trip with children.

FULL 14 day Itinerary for your Critique

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