Four Road Trips to Take from San Francisco This Long Weekend

San Francisco has been called the most European city in the United States with its architecture, culture, and fascinating people. At the same time, those who live in San Francisco, as well as those who visit occasionally, need to take a break from this magical city and get away for a long weekend. We’re sharing some of our favorite road trips from San Francisco for a long weekend getaway, but they’re also great for almost any time you need a weekend getaway from San Francisco.



Four Road Trips to Take from San Francisco This Long Weekend Bolinas
Photo courtesy of Smiley’s Saloon & Hotel


Bolinas is so special that the locals have a reputation for removing road signs that direct visitors to the enclave. But, if you can find your way (it’s not too difficult), you’re in for a treat and you’ll understand why the locals allegedly remove the signs. Bolinas is home to the oldest continuously-operated saloon in the state of California and possibly west of the Mississippi River. Known as the “best party in town”, Smiley’s has been a community staple since 1851 during the gold rush days.

Bolinas is the perfect road trip during which you can unplug. Bolinas, as well as many of the smaller communities in Northern California, has some pretty sketchy cell service and to fully unplug and enjoy the live bands and local watering hole, we recommend you stay right at Smiley’s. They have a handful of simple rooms that are free from telephones and televisions and the internet. You could also opt for a stay at The Grand Hotel which has an equally storied past. Lore tells us that The Grand Hotel wasn’t ever intended to be an actual hotel. It turns out that the owner found a sign he liked and hung it on his house as decoration. People kept stopping in to see if he had any rooms and eventually he relented and accidentally became an actual hotel.

San Luis Obispo


Four Road Trips to Take from San Francisco This Long Weekend San Luis Obispo
Photo courtesy of Madonna Inn


While this destination is much further at more than a three-hour drive away, it is worth the drive once you arrive in San Luis Obispo (SLO). They have an airport, so you could technically take your road trip to the skies, but we recommend you make the drive – it’s most enjoyable. SLO is known for its proximity to great wine, being home to great food, gorgeous beaches, and the best hiking. They also have an amazing open-air market downtown on Thursday nights featuring live entertainment, wares from local artists, and more.

If you’re a hiker, you’ll want to climb up to Bishop’s Peak; if you’re a lover of beer, you’ll enjoy the Hop-On Beer Tour; and, if you love kitsch, you’ll want to stay at the iconic Madonna Inn. As they note, “Madonna Inn is an international destination resort, welcoming guests since 1958 with 110 unique guest rooms, beautiful architecture, and onsite experiences.” Those experiences include a most memorable facility, Alex Madonna’s Gold Rush Steakhouse, Copper Café, Silver Bar Cocktail Lounge, and the Terrace Pool Bar. Beyond eating and drinking, you’ll be able to enjoy the pool and fitness center, horseback riding, boutique shopping, live music and dancing, on-site wine tasting, hiking, biking, tennis, basketball, and garden games.



Four Road Trips to Take from San Francisco This Long Weekend Yountville
Photo courtesy of North Block Hotel


Less than a couple hours north of the city (depending on how you time your drive), you’ll find Yountville. It’s a tiny town in the heart of the Napa Valley that allows you to experience the beauty and charm of Napa without interfacing with tons of tourists (people on road trips don’t count as tourists, right?).

The beauty of Yountville in addition to the lack of huge crowds, is that you’ll experience everything that draws you to Napa – great food (Redd Wood, Bouchon, and Ad Hoc are all right there), great wine, and great outdoor activities. Those great activities include hot air balloons (the best way to see the entire Napa Valley) and amazing bike riding. There are great bike rentals that will steer you to the six-mile bike trail stretching from Yountville to Napa where you can find some of California’s best wineries. Our pick for accommodations is the North Block Hotel. It’s chic and sophisticated and offers all the amenities to make your weekend road trip most memorable.

Virginia City



It may seem like a long journey for a road trip, but the charm of this colorful little mining town is completely worth spending an afternoon getting there. Virginia City, Nevada has its own level of cheesiness, but it’ll teach you about the gold rush days and the gold strikes when you take the narrated four-mile train ride with V&T Railroad. There’s no need for a vintage photo booth in Virginia City because nearly every spot is a historical backdrop. You’ll also have fun on a gold-rush era saloon crawl at any number of the 15 Old West saloons within walking distance of each other.

This is small town America so your lodging options are limited, but our pick is the Silver Queen Hotel. It’s a western-themed hotel that dates back to 1876. The hotel notes that they are “located in the center of Virginia City. Spend an evening in Virginia City’s past away from phones and televisions. The Silver Queen hotel was built in 1876 and offers 28 beautifully restored rooms, some with 16 foot ceilings. Each room features its own private bathroom, including a shower or an authentic claw foot bathtub.” While it may not be high luxury, it is definitely high period with its beautiful rooms. You’ll be staying and fully experiencing history at this quaint hotel which is also has a wedding chapel!

San Franciscans love their city, but they also love a good road trip. Whether you’re located in the city or just visiting, a road trip is definitely in order. To which of our destinations will you be road tripping? For more northern California greatness, plan another weekend with our help: Your Perfect Napa Valley Weekend.

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Four Road Trips to Take from San Francisco This Long Weekend