DriveShare San Francisco: Travel Guide

Now that you’ve reserved your DriveShare classic, luxury or sports car rental, we want you to truly Enjoy the Drive and love your time behind the wheel in San Francisco. For that, you’ll need some top-tier destinations on your itinerary featuring some of the best things to see from behind the wheel around the Bay Area.

San Francisco and the stretches of Northern California beyond the city limits offers some of the greatest driving destinations in the country. From the famously hilly SF streets to the rolling hills of Wine Country to the PCH and Big Sur, your DriveShare vehicle is the gateway to some amazing landscapes, country lanes and roadside attractions. 

To help you enjoy the drive, we’ve assembled some great cruising destinations inside and beyond the city limits for you to get behind the wheel and find some great San Francisco area attractions. Let’s hit the road! 

In the City: Drive the “Scenic 49”

If you want to cruise to some of the most famous sites around San Francisco without having to plan your own itinerary, good news: Some very helpful people in the late ‘30s already thought of that for you. Created in advance of the Golden Gate International Exposition in 1939-40, this 49-mile scenic drive covers a ton of ground and shows you all the amazing things that downtown SF has to offer. 

You’ll start off at City Hall, affectionally known as the People’s Palace. The route also takes you down the city’s famously-crooked Lombard Street, past Fisherman’s Wharf, along the Embarcadero and up Nob Hill, beneath the Bay Bridge, through neighborhoods like Haight-Asbury, Chinatown, Cole Valley and the Castro. You’ll also get to pass through part of Golden Gate Park, cruise past the Palace of Fine Arts and many more SF destinations. 

Is this the fastest way to see the city? Well, you’re driving through a very urban area where you’re traversing hills and dodging cable cars, so no … but since you’re in a DriveShare car, you might want to take it slow and give people a good look at your awesome ride. 

Wind through Wine Country 

Now that you’ve seen the city, it’s time to stretch your legs, hit the gas and get to the country: Wine Country. Starting from SF proper you get to cruise your cool DriveShare car across one of America’s most famous stretches of suspended pavement: The Golden Gate Bridge. Once you’re across the 1.7 mile span, it’s a nice drive past the Marin Headlands on US Route 101 around San Pablo Bay up to Napa. 

From here, the most famous (and popular) drive is along the Silverado Trail from Napa to Calistoga. This will take you past plenty of prestigious wineries (we’re personally fans of Mumm Napa) and luxurious resorts like the Solage Calistoga, part of the Auberge Resort family. Michelin-caliber restaurants dot the landscape, so a great meal is never far from whatever milepost you’re closest to. 

From Calistoga (after taking a side trip to the Petrified Forest for a hike through their famous fossilized foliage) we head over to the aptly named “Wine Road” which takes drivers through even more famous valleys like Russian River, Dry Creek and Green Valley to visit wineries including Kendall Jackson, Merry Edwards and Emeritus Vineyards (plus one of America’s most famous breweries: Russian River Brewing). 

Photo: Christopher Michel

Seaside cliffs at Big Sur

One of the ultimate SF roadtrips is the four-hour excursion down Highway 1 to Big Sur’s famous seaside cliffs, soaring bluffs and misty mountainsides. It’s a National Scenic Byway and well worth extending the drive in your DriveShare to a full day or two for stops in Monterey, Santa Cruz and Carmel. 

Your first stop outside San Francisco will be Half Moon Bay, a tourist-friendly surfer town that’s less than an hour from downtown SF but feels so rural you’ll think you’re hours away from one of the country’s biggest cities. From here we head further south (past the famous Pigeon Point Lighthouse) to the beachfront boardwalk of Santa Cruz, complete with a historic wooden roller coaster and a wharf jutting out into the Pacific. 

After swinging through Monterey for a stroll along the town’s famous Cannery Row, plan to spend a few hours enjoying the city’s famous aquarium, home to otters, penguins and sharks. From here you’ll be spending a few bucks to take a drive along the famous 17-Mile-Drive through Pebble Beach golf course (though guests of the Lodge at Pebble Beach get free admission, so if you’re considering an overnight stay with your DriveShare). 

Once you’re through the gates, be ready for a slow cruise along one of the most scenic oceanfront roadways with amazing cliffs, ancient trees, snow-white beaches and amazing sunsets (another reason to spend the night). 

From here we cruise through Carmel-By-The-Sea (where Clint Eastwood was famously elected mayor) along even more amazingly scenic Pacific Coast Highway miles, cross the famous Bixby Street Bridge to finally arrive in beautiful, scenic, secluded Big Sur. Its remote location makes it great for hiking, beachgoing and camping (or, for a bit more comfort, “glamping”). 

If you’re looking for a few more creature comforts, there are a handful of luxury resorts like the Post Ranch Inn and the adults-only Ventana Inn & Spa will make for a safe, secure resting place for your DriveShare vehicle while you take in the ocean view with a glass of California wine. 


Have these routes inspired you to take a drive but you need a suitably classic car to cruise these highways and byways? Get started at Hagerty DriveShare, then get ready to fire up the engine and hit the road. 

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