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pls advice best driving routes & hours (for newbie driver) re:SF~Big Sur & Big Sur~Napa

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Hi all, I'm leaving for San Francisco soon and doing two side trips. So excited, as this is my first road trip! Can you guys please advise the best driving routes for my destinations? And when will be the best hour in the day to drive during those routes. Thanks in advance! (Oh and please be as DETAIL as possible...new driver here, thanks!)

Proposed itinerary:
Thurs-Sat: SF, overnight in SF
Sun: SF~Monterey, overnight in Monterey (Anno Nuevo, Monterey, Pacific Grove/17 mile/Pebble Beach and Carmel)
Mon: Big Sur, overnight in Monterey (Point Lobos, Pfeiffer Big Sur State Park, Julia Pfeiffer Burns and Nepenthe)
Tues: Monterey~Napa, overnight in Napa
Wed: Napa and Sonoma, overnight in Napa
Thurs: Napa~SF International Airport for flight (by 10:30am)

(A) San Francisco ~ Monterey on SUNDAY

1. Best scenic route? (Picking up a friend from Holiday Inn near Nob Hills before departure, intersection of Van Hasse-Hwy 101 & California St.)
2. Driving southbound on Hwy 1 from SF on a Sunday, is it busy? Depart the earlier the better?
3. Will we have time for Point Lobos in late evening? Or is it better to do it morning on next day?

(B) Monterey ~ Napa on TUESDAY

1. Fastest route? Through San Jose/Fremont/Walnut Creek or SF? Which route is quickest on a TUESDAY morning?
(Both Michelin and Google suggested the first, but a fellow Fodorite suggested through taking Hwy 101 through SF instead)
2. This is the route that I'm most concern about, if there are certain points on the way that it's easily missed or confusing, please kindly point them out.

(C) Napa ~ San Francisco International Airport on THURSDAY

1. Must be there by 10:15am for check-in! The fastest and surest route?


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