Can I drive from San Diego to Portland and have a good time?
– Leave San Diego on Monday, get to Portland on Wednesday Unfortunately, you’re not going to be able to see much in your timeframe, as it takes 15-18 hours to *just* drive from San Diego to Portland on the fastest route through California — straight up Interstate 5 with no deviation. This is also the least scenic of the routes. Any other north-south route (e.g. the 101, the 99, the 395) adds significantly to the drive time, so it may not fit into your 3-day window. Your plans to “see a bit of wine country” may just mean driving through San Francisco and back to the 5 via Napa. You need to add more time to your agenda to really get anything done. And there is a lot to do, don’t get me wrong. If I had all the time in the world, it’d be 101 through Santa Barbara, the 1 through Big Sur, Monterey and Santa Cruz, to S.F., through Eureka and the redwoods back on the 1, and on up the coast to Astoria.
