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Milan, Italy

Stefano from Milan, Italy asked

30 days by car around: SF, Portland... and then ?

Here Stefano, graphic designer&music journalist from Milano-Italy

me my wife and our beautiful little baby (3 month old), we'll be from 6th oct. to 6th nov. in USA 

it's our first time on the West Coast, and we'd like to have  a lot of suggestions from Trippy community!

here our plans, or better, here just some fixed-points (but, we're still organizing/thinking on):

5 days in SF city (any suggestion to a not expensive sistemation? also airbnb apt seem to be quite expensive there!!)

then we rent a car and we go... (where? :-)

for sure:

- we want to arrive to Portland (and then stay there 3-4 days) and visit Seattle
- I want to fishing salmons somewhere in Oregon !
- 1 or 2 days in Las Vegas
-  visit my wife's parents nearby Los Angeles
- maybe somewhere in Silicon Valley ? (but where and to do what? :-)

and then we are open to your suggestions! :-)

we love to discover all the unusual places, little villages, the "deeeeep country".

we love flea market & second hand store (!!!)
we love to eat local food.
we love to discover some impressive new-street art artist (we've got a little online art-gallery:

feel free to write any suggestion, all your secret places are welcome :-)

thank you very much in advance


San Francisco (California)   Portland (Oregon)   Seattle (Washington)   Las Vegas (Nevada)   Los Angeles (California)   Silicon Valley (California)   San Jose (California)   Palo Alto (California)   Menlo Park (California)   Redwood City (California)

10 Answers
top answer by
Kristin from New York City

I love this question! You're going to have a great trip no matter what you do. A few tips from me:

- Start your trip further up the coast... Perhaps fly into Portland if possible, spend a few days in the Alberta Arts District of Portland and head South from there. 

- Go East and South through Oregon, hitting Mt Hood and Crater Lake National Park if your family likes nature. Go through the towns of Bend and Eugene (You can skip Eugene, in my opinion, but you'll pass through it as you head to the coast if you decide to go south first).

- Hit Florence (Oregon) or the surrounding towns for a cool Pacific NorthWest experience

- Drive South through California hitting the following coastal towns/cities:

San Francisco

Sonoma (maybe scratch this knowing you're from Italy and have far superior wine country)

Berkeley (Great area for the arts)


Big Sur 

San Luis Obispo

Santa Barbara

Santa Monica

Palm Springs

These are just recommended cities to hit and if you want to journey further inland to see some amazing parks, you can head towards Lake Tahoe and Yosemite National Park Rd

Happy to provide camping/hotel/other local recommendations as you plan!

Comments (2)

grazie ! thank you very much !!

I should look out for this answer when i decide to visit the West Coast!

Mentioned in this answer:

  1. Alberta Arts District (neighborhood)
  2. Mt Hood (attraction)
  3. Crater Lake National Park (park)
  4. Bend (city)
  5. Eugene (city)
  6. Florence (Oregon) (city)
  7. San Francisco (city)
  8. Sonoma (city)
  9. Berkeley (city)
  10. Monterey (city)
  11. Big Sur (city)
  12. San Luis Obispo (city)
  13. Santa Barbara (city)
  14. Santa Monica (city)
  15. Palm Springs (city)
  16. Lake Tahoe (attraction)
  17. Yosemite National Park Rd (attraction)
comments (2)
likes (8) thanks
answered first by
Tony from Seattle

Whoa, you could write a whole book on this stuff, but I'll start out with some broad thoughts.  You might consider asking a few questions!

San Francisco is pure insanity in terms of price right now (thanks, internet).  Consider staying outside of SF and day-tripping into the city.

North is WAY prettier than west.  Tomales Bay is gorgeous, as is Point Reyes National Seashore.  Mill Valley (California) might be a good place to base out of.

Portland is amazing.  Stay on the east side of the river.  See the Multnomah Falls.  Walk thru Ape Cave (2 miles of walkable lava tubes!).  Hit Cannon Beach on the way in or out.

Seattle is amazing, too.  If you get that far north, get to the San Juan Islands - they are gorgeous.

You won't be in salmon season, but there will be some fishing you can do (trout, etc).

Hope some of that is helpful!  Keep asking more/specific questions-- these big/broad ones are hard to answer!

Comments (1)

thank u very much tony!!! i'll be back soon with some other questions ! :-)

Mentioned in this answer:

  1. San Francisco (city)
  2. Tomales Bay (attraction)
  3. Point Reyes National Seashore (attraction)
  4. Mill Valley (California) (city)
  5. Portland (city)
  6. Multnomah Falls (attraction)
  7. Ape Cave (attraction)
  8. Cannon Beach (city)
  9. Seattle (city)
  10. San Juan Islands (attraction)
comments (1)
likes (7) thanks
answered by
Scott from Fort Collins


Greetings!  Sounds like a fantastic vacation!  There are so many ways you can do this, but 30 days might be a challenge to incorporate Las Vegas, Los Angeles and the upper Pacific Coast by car.  I can give you a recent itinerary I did from Klamath Falls, Oregon to Portland and up to Seattle.  I came from Reno/Tahoe, but, Oregon is a wonderful drive.  I have also spent some time in Napa, so if you like wine, please take a day, or two, here.  Some of my favorite wineries are, Caymus VineyardsFlora Springs WineryPine Ridge Vineyards, and great restaurants are Gott's RoadsideThe French Laundry, Bounty Hunter Wine Bar & Smokin' BBQOakville Grocery

If you can work your way up to Klamath Falls (Oregon), Oregon, from California, spend a night around Crater Lake National Park. Drive over to Coos Bay, Oregon and drive north on 101.  There are many cute little towns to stroll and shop.  You can drive to Portland using many roads and it completely depends on your opinions.  You can drive over to many spots in Willamette Valley for world class Pinot Noir, or continue on 101 and stay somewhere around Seal Rock and drive up to Astoria where I would recommend staying at the Cannery Pier Hotel.  I don't know much about Portland, but I would also recommend a drive to Mount Saint Helens on your way from Portland to Seattle.  Seattle has some fantastic ethnic cuisine, and especially fresh fish.  I'll try to do more research and respond, but I'm on vacation!  :). Hope that helps!

Comments (2)

thank you scott!

Sounds awesome, Scott!

Mentioned in this answer:

comments (2)
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answered by
Mary Ann from La Jolla

For San Francisco, and lower hotel rates, you might consider staying in Berkeley, Emeryville or Oakland and taking  BART into the City. After you pick up your car--perhaps Sonoma Valley; Highway 1 north of SF; SeattlePike Place Market; Pioneer Square; Seattle Art Museum; Olympic Sculpture Park; Ferry to Bainbridge Island.  South of SF:  Half Moon Bay/Carmel/Monterey. San Jose has the San Jose Museum of Art, The Tech Museum of Innovation, Sprouts Farmers Market; Heading toward LA...down the central coast and the wine country in Santa Lucia Highlands/Paso Robles/Santa BarbaraSanta Maria/Santa Ynez/San Luis Obispo etc.

Comments (1)

thank you mary ann !

Mentioned in this answer:

  1. San Francisco (city)
  2. Berkeley (city)
  3. Emeryville (city)
  4. Oakland (city)
  5. Sonoma Valley (attraction)
  6. Seattle (city)
  7. Pike Place Market (attraction)
  8. Pioneer Square (attraction)
  9. Seattle Art Museum (attraction)
  10. Olympic Sculpture Park (attraction)
  11. Bainbridge Island (city)
  12. Half Moon Bay (city)
  13. Carmel (city)
  14. Monterey (city)
  15. San Jose (city)
  16. San Jose Museum of Art (attraction)
  17. The Tech Museum of Innovation (attraction)
  18. Sprouts Farmers Market (attraction)
  19. Santa Lucia Highlands (region)
  20. Paso Robles (city)
  21. Santa Barbara (city)
  22. Santa Maria (attraction)
  23. Santa Ynez (city)
  24. San Luis Obispo (city)
comments (1)
likes (4) thanks
answered by
Peter from Bloomington (Indiana)

Between Los Angeles and San Francisco is one of the most beautiful coastal highways in the world. You should rent a car and drive it, spending as much time as possible on Highway 1, which follows the coast. Some very special places include:

Santa Barbara, a gracious small city with a Spanish heritage and a beautiful old mission. (The Spanish built 21 Catholic missions in the 18th Century, and they are all still standing.)

Hearst Castle, at San Simeon. You will have seen much larger castles in Europe, but Hearst Castle may be the closest thing to a European palace that any American has ever built. (Its creator was William Randolph Hearst, the media baron who built it to satisfy his vanity and impress his Hollywood friends.)

Paso Robles, an increasingly popular place to visit wineries and taste excellent California wines.

Big Sur, one of the most beautiful sections of the coast. Stop at Julia Pfeiffer Burns State Park to see one of the most beautiful waterfalls. Have a light meal and a drink at Nepenthe -- get a seat outdoors on the very top level for the best view of the scenery.

Yosemite Valley (California) -- Drive inland about three hours to one of the most magnificent national parks in North America.

My favorite California beach is Pescadero State Beach, a magnificent, unspoiled place north of Monterey and Santa Cruz.

Napa and Sonoma -- Paso Robles is beginning to rival Napa and Sonoma for wine tasting, but these are still the originals. Domaine Carneros has great sparkling wines. Luna Vineyards is lovely for Italian varietals -- try the Sangiovese. Del Dotto Estate Winery & Caves also is Italian-inspired. But there are many, many more vineyards offering tastings every day. In Sonoma, have a late breakfast at the Fremont Diner -- it doesn't look like much from the outside, but it is a real experience.

Marin County -- simply one of the loveliest regions in the US. We like the Buckeye Roadhouse for dinner in Mill Valley, just off Highway 101. Visit the giant redwood trees at Muir Woods National Monument and the forest at Mount TamalpaisMuir Beach is good for swimming. Marin Headlands has a spectacular view of San Francisco and the Golden Gate Bridge.

San Francisco is a huge subject all by itself. San Francisco Chinatown is worth an afternoon. Just driving in the city is an experience, because of the extreme inclines on many streets -- driving down the absurdly twisted Lombard Street is worth doing once. Alamo Square has lovely old Victorian houses -- affectionately known as the "Painted Ladies." Golden Gate Park has many attractions, including the Conservatory of Flowers, and a very fine collection of art at the De Young Museum. (Your admission ticket also gives you access to the California Palace of the Legion of Honor, which houses an even larger collection, including great classical European paintings.)  Do NOT bother going to Fisherman's Wharf -- it is famous, but crowded and not very interesting. 

Comments (3)

Great spots Peter!

Hi peter we had a lunch at Fremont Diner today: W O N D E R F U L L. thank you very much for the advise !

Prego, Stefano.

Mentioned in this answer:

  1. Santa Barbara (city)
  2. Hearst Castle (attraction)
  3. Paso Robles (city)
  4. Big Sur (city)
  5. Julia Pfeiffer Burns State Park (attraction)
  6. Nepenthe (restaurant)
  7. Yosemite Valley (California) (attraction)
  8. Pescadero State Beach (attraction)
  9. Napa (city)
  10. Sonoma (city)
  11. Domaine Carneros (attraction)
  12. Luna Vineyards (restaurant)
  13. Del Dotto Estate Winery & Caves (attraction)
  14. Fremont Diner (restaurant)
  15. Marin County (region)
  16. Buckeye Roadhouse (restaurant)
  17. Muir Woods National Monument (attraction)
  18. Mount Tamalpais (attraction)
  19. Muir Beach (city)
  20. Marin Headlands (attraction)
  21. San Francisco Chinatown (attraction)
  22. Lombard Street (attraction)
  23. Alamo Square (attraction)
  24. Golden Gate Park (attraction)
  25. Conservatory of Flowers (attraction)
  26. De Young Museum (attraction)
  27. California Palace of the Legion of Honor (attraction)
  28. Fisherman's Wharf (attraction)
comments (3)
likes (4) thanks
answered by
Debbie from San Francisco
This is a lot of stuff to do! Good for you :) Yes, San Francisco is ridiculously expensive! If that's an issue, I recommend staying in the East Bay, like in OaklandBerkeleyAlbany (California) or El Cerrito.  All are within a 15-30 minute subway ride to San Francisco (like riding the train from Brooklyn to Manhattan). Just make sure you're close to a BART station. You can see the BART map here. That way, you wouldn't need a car because that's just a hassle in San Francisco. In Oakland, there's a First Friday and First Saturday event called Art Murmur that you'll unfortunately just be missing by a hair (it's October 3rd and November 7th). But -- you can probably check out the art galleries anyway. Here's their website with a list of cool urban art galleries. For art in San Francisco, check out the Clarion Alley in the Mission District.If you do rent a car, you can also drive out to the 16th Avenue Tiled Steps ProjectAnd Lands End for the labyrinth For local food, there's the lovely Ferry Plaza Farmers Market every Thursday and Saturday afternoon. Not only can you get local produce, but you can get prepared food from the food stands as well. For thrifting, there are tons of of thrift stores in the Haight-Ashbury district. Do you have any specifics that you want to see in Silicon Valley? If you have friends who work at any of these companies, maybe you can get a tour at Facebook Inc.Googleplex or Apple Incorporated. So you'll be driving up to Portland and Seattle.  On the way to Portland from San Francisco, I suggest stopping by Muir Woods National MonumentAnd Stinson Beach And Redwood National ParkThe lovely town of Ashland (Oregon). Cute scenic town. Or at least stop by the The Black Sheep Pub & Restaurant for a meal. There are also some good thrift stores there if you walk around.In Portland, check out the food truck pods. There's the one that Potato Champion is in (great poutine!), and there's the one next to Prost!. You can order food at the food trucks and eat it at the bar.For thrifting, check out the Goodwill that's behind Umpqua Bank. It's the fanciest Goodwill I've ever been to. And if you walk around that neighborhood, you'll see a ton of other cool restaurants and stores. In Seattle, you should look into staying near the Pike Place Market or Capitol Hill Neighborhood to be centrally located. You can check out this other post on Trippy for things that you should see in Seattle in a short amount of time. Honestly, I think Vegas is overrated, and it's out of your way. Plus, I don't think it would be so fun with a baby, so I would save time and money, skip it, and focus on all the other destinations. I would fly straight down to Los Angeles from Seattle. There's so much to do in LA. Tons to eat and so many beaches to hit up. Let me know if you have any questions. I hope you have fun! :)

Comments (1)


Mentioned in this answer:

  1. San Francisco (city)
  2. Oakland (city)
  3. Berkeley (city)
  4. Albany (California) (attraction)
  5. El Cerrito (city)
  6. Clarion Alley (attraction)
  7. 16th Avenue Tiled Steps Project (attraction)
  8. Lands End (attraction)
  9. Ferry Plaza Farmers Market (attraction)
  10. Haight-Ashbury (attraction)
  11. Facebook Inc. (attraction)
  12. Googleplex (attraction)
  13. Apple Incorporated (attraction)
  14. Portland (city)
  15. Seattle (city)
  16. Muir Woods National Monument (attraction)
  17. Stinson Beach (city)
  18. Redwood National Park (park)
  19. Ashland (Oregon) (attraction)
  20. The Black Sheep Pub & Restaurant (restaurant)
  21. Potato Champion (restaurant)
  22. Prost! (attraction)
  23. Umpqua Bank (attraction)
  24. Pike Place Market (attraction)
  25. Capitol Hill Neighborhood (neighborhood)
  26. Los Angeles (city)
comments (1)
likes (4) thanks
answered by
Siri from Oslo

Drive down highway 1 from San Fransico to LA. Beautiful scenary. Spend a few days on the road so you can stop along the way. I recommend a stop in beautiful Carmel. Charming small houses, local food and local wine. Drive down to the beach to see the sunset in the evening, it its lovely. Also Santa Cruz i worth a visit here you can just hang on the beach and watch the sufers or you can ride the roller coaster right on the beach. The city also got kind of a hippie vibe to it so it has a great and unique atmosphere. Our best moments on this trip tho was when we just decided to pull up somehwere along the road and watch the nature or go for a hike.

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answered by
Marvin Paul from Milpitas

When you're passing through Silicon Valley stop by Big Dog Vineyards on a Saturday or Sunday. It's off the beaten path with a scenic drive and great views.

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Mentioned in this answer:

  1. Big Dog Vineyards (restaurant)
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answered by

I highly recommend catching a Timbers game Providence Park game when you're in Portland.  Tickets can be tricky, so plan ahead (tho you can always pick them up from scalpers).  There is a ton of great food in Portland.  The Deschutes River is a great place for flyfishing, as is the Metolius River.  Contact a fly shop or guide service for details.

Comments (0)


Mentioned in this answer:

  1. Providence Park (attraction)
  2. Deschutes River (attraction)
  3. Metolius River (attraction)
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answered by
Steve from San Francisco

 I urge you to drive either up, or down highway one to Big Sur. Preferably in a convertible. Stop at Nepenthe. Find the one lane road down to Pfeiffer Beach Day Use Area. Stay at Ripplewood Resortif you can. I can't over recommend this. 

Comments (0)


Mentioned in this answer:

  1. Nepenthe (restaurant)
  2. Pfeiffer Beach Day Use Area (attraction)
  3. Ripplewood Resort (restaurant)

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