San Francisco in a Weekendfeatured

Whenever I’m asked my favorite city to visit in the US, I don’t hesitate to give an all too immediate answer: San Francisco.

I’ve never written of my visits, sharing pictures instead. A picture is worth a thousand words, and when I’m in San Francisco, all of the words float around my head, a line direct from my heart. I often go to San Francisco when I’m at a crossroads or when I need peace, finding my answers and solace in quiet mornings at Crissy Field, watching the fog roll in over the bridge. It’s an easy visit to make –since Virgin America began direct daily flights from Chicago to SFO back in 2014, the competition between Virgin, American, Southwest and United creates pockets where airfare is unbelievably low.

A few years ago, I began traveling the weekend before my birthday and when my birthday crept up on me, lost in a string of long workdays and the Chicago summer heat, I weighed my options: somewhere new, maybe. Portland, Salt Lake City, Denver – they’re all on the list. But airfare to San Francisco was too low to pass up, and more than that, Stephanie had never been to San Francisco before and I loved the idea of showing my sister around the city that holds a piece of my heart back with it every time I leave.

So Stephanie and I met up at O’Hare on a scorching summer day, clearing an upgrade to First six minutes before boarding a flight 1846 miles west, to a city that was 20 degrees cooler.

Where We Stayed

I’ve always stayed with friends when I’ve visited San Francisco, so when it came time to look for a hotel, I knew two things: one, real estate in San Francisco isn’t the only thing skyrocketing – so are nightly hotel rates and two, we were renting a car and the cost of parking over a long weekend could exceed our airfare in some of these neighborhoods. You can stay out in Oakland, but the rising cool factor has upped the nightly hotel rates there, too. A better option if you’re renting a car is to stay just outside city limits – hotels in San Bruno, Brisbane, Daly City or one of the other towns that lay in between the airport and San Francisco proper not only have lower nightly rates, but often times also have free parking.

I found a hidden rate on Hotwire for a hotel in Oyster Point that I could decipher as the Inn at Oyster Point, and reviews on Trip Advisor raved over the heartfelt service, the quirky décor and the complimentary room service breakfast. The Inn also featured a fireplace in every room and free parking and was a short ride from the airport, a definite perk when your flight lands in the late evening.

Trip Advisor has never led me wrong and this was no exception. Not only were the accommodations clean and comfortable, we were just a short drive from city limits, and starting our days with a hot cup of coffee and a bagel in an oversized plush armchair, looking out over the marina was the perfect way to start a day.

Making an Itinerary

Stephanie and I flew out on Friday night and home late on Monday afternoon, which gave us two and a half days. If you’re visiting San Francisco for the first time, two days should be just about enough to see and enjoy the major sites. San Francisco isn’t that big (…says the Chicagoan) and it’s easy to traverse when you have a car (as long as you’re comfortable driving up and down those steep hills!).

But if you’re looking to venture outside of the city into wine country or to see the redwoods, those excursions can easily take up a half or a full day. I didn’t just want to show Stephanie the major sites – I wanted her to experience them. And I wanted to show her a little bit of what lays outside of city proper, too.

So below is a list of what we were able to see and do in two and a half days. It’s by no means a list of everything to see, but rather my favorite things and places to visit when you’re only in the city for a couple of days at a time.

Walk Along the Shore at Baker Beach

The first thing we did on our very first morning in San Francisco was drive through the Presidio towards Baker Beach, windows down. Eucalyptus trees grow in the forest around the Presidio and it smells amazing.

What I love most about Baker Beach are the views of the Marin Headlands and Golden Gate Bridge in the distance. It’s so distinct, majestic almost, especially when there’s fog rolling in. Our visit came on a Saturday morning, so the beach wasn’t crowded. The air was warm and the sun was shining, giving us a picturesque view of the bridge as we kicked off our shoes and walked along the water’s edge.

Dig Into Some Dim Sum (no, seriously, do it)

San Francisco is known for its fresh seafood. My friends who live out that way swear it’s the best they’ve ever had. But I don’t eat seafood at all, and Stephanie will only eat tuna salad and smoked salmon, so a lunch of fresh crab or oysters wasn’t in the cards for us. But one of the most wonderful parts of San Francisco is the cultural diversity – the city is a mixing pot of so many ethnicities and cultures – and that manifests itself in some amazing eateries.

On my first visit to the Bay area, my friend took me to Yank Sing, a traditional dim sum restaurant that is often considered as one of the best in the US, and to this day, I dream of their steamed bbq pork buns. Yank Sing serves dim sum the traditional way: off rotating carts. We ordered a variety of dumplings, buns and other dim sum delicacies, each better than the last.

Shop the Weekend Market at the Ferry Building

The Ferry Building is one of my favorite places in San Francisco. Right on the Embarcadero (with a wonderful view of the Bay Bridge), the Ferry Building houses dozens of small boutiques, cafes and gourmet shops. It’s a wonderful place to pick up unique gifts for friends (especially foodie friends!) and enjoy some local eateries.

On the weekends, there’s a market in front of the building, with handmade craft booths, farm fresh produce, freshly cut flowers and pop ups. It can get pretty crowded, but it’s so fun to browse. I love how the city embraces small businesses and local farms.

Walk Along the Embarcadero to Pier 39

The Ferry Building is awesome, but it’s not huge, and a visit doesn’t take more than an hour. A short stroll up the Embarcadero will take you to Pier 39, a boardwalk with all kinds of quirky shops, restaurants and attractions.

I love to walk around Pier 39. I’ll grab a snack (usually some of that amazing sourdough bread from Boudin that’s so notoriously delicious that they sell it in the souvenir shops at SFO) and I’ll look around the shops, but I always end up by the sea lions.

Pier 39 also has the best views of Alcatraz. You can book boat tours to Alcatraz, too, but I’ve always been content to just look from a distance.

Snap the Sites

There are so many famous sites to see in San Francisco. The Painted Ladies in Alamo Square, the Full House house, Cupid’s Span, Haight Ashbury, the Golden Gate Bridge, the Bay Bridge, Lombard Street (the most crooked street in America – best of luck to you if you try to drive down it because we certainly did not have the guts to do it), Fisherman’s Wharf, Ghiradelli Square, Golden Gate Park, the Castro…the list goes on and on and each one is better than the last.

We didn’t spend a ton of time at all of these sites. Some of these we just drove past and others, we parked the car and walked around. Some are further away than others so it’s definitely helpful to know what you want to see and lay them out in a Google Map to understand their proximity to each other and what the most efficient route is.

Make the Drive to Wine Country

An hour north from the busy San Francisco metro area the Napa/Sonoma region, an area renowned for the best wine made in the USA. There’s over 400 wineries and vineyards and a trip up to wine country could really be a weekend trip of it’s own, visiting a string of wineries, hiking and biking along the winding roads and visiting some of the best spas in Northern California.

We thought about doing a day in Napa (because between the drive and the time you’ll want to spend at a winery or three, it’s just about a full day proposition), but we didn’t have a designated driver and we had so many other things to see. So instead of showing Stephanie my favorite places in Napa and Sonoma (Domaine Carneros and Ram’s Gate, if you’re planning on going out that way), we headed out towards Bodega Bay for a wine tasting at Gourmet au Bay, a small wine bar on the water’s edge that I discovered on my first visit to San Francisco. We sipped on some amazing (and locally produced!) wines and enjoyed the peaceful, laid back vibe before heading out to Sausalito for dinner.

See the Sunset in Sausalito

Just north of San Francisco, across the Golden Gate Bridge, is Sausalito, a small costal town that hugs the bay. It’s a perfect stop when you’re driving back from wine country, and there are tons of restaurants and shops and a great view of San Francisco’s skyline. My favorite thing to do in Sausalito, though, is walk around at dusk.

We parked the car in one of the public lots, grabbed some tacos at a nearby Mexican restaurant and ice cream from the local creamery and settled in to watch the sunset over the marina.

View the City from the Top

San Francisco is a city of highs and lows – literally. Some of the streets wind around in crazy curlicues and others go straight up (and down) at angles that seem to defy gravity. But the best way to see the city is from the very top and San Francisco has some amazing vistas.

The best view of the city from within the city is at Twin Peaks, a pair of hills in the center of the city that make up the second highest point in San Francisco (just three feet shorter than the tallest point at Mount Davidson). The drive up isn’t too scary and on a clear day, you can see out for miles. And, on a not so clear day, you can watch the fog roll in over the city. That’s kind of cool, too.

My favorite view point in San Francisco, though, is Battery Spencer. There are many places to take in a great view of the bridge. Crissy Field and Baker Beach are two great ones. You can walk across the bridge or even take a boat ride in the bay. But like the city, the best view of the bridge is from up top. Battery Spencer is an old military fort on the north side of the bridge. We went at night on our way back from Sausalito and it was super dark, super cold and super windy. It’s a trek from the parking lot to the viewpoint (just about a quarter mile) and we had to use our cell phone flashlights to find our way, but it was 100% worth it for the view.

The bridge lights up at night, the orange bright against the black sky, with the city lights twinkling in the background. It is magical.

Go Off the Grid

If it isn’t already obvious, I try to spend as much time outside as possible when I visit San Francisco. The weather trends towards mild most of the year, and on a sunny day, there’s no better way to spend a couple of hours than with a picnic on the Presidio.

Every Sunday from March through October, Off the Grid (a traveling market of food trucks and local vendors) sets up at the main parade ground. Dozens of food trucks line the perimeter and tents pop up along the middle with locally made foodie treats and artisan wares. Locals flock to the lawn on Sundays with their families, friends and pets and lay out a blanket while they feast on some of the best street food in the Bay area. My friends and I would always make a stop at Off the Grid for a quick early lunch before heading to Napa – the Presidio location (on the south end of the Golden Gate Bridge) makes it a perfect stop on the way to wine country – and since we don’t have much of a street food scene in Chicago, I knew Stephanie would love it.

We grabbed some grilled cheese nachos from one vendor and some snow ice treats from another (Horchata snow ice + Tcho chocolate = best combo ever!) and parked out on the lawn for an hour on a gorgeous, sunny Sunday.

Stroll through the Redwoods

The Bay area is home to a series of temperate rainforests where Redwoods trees (some of the tallest trees on earth!) grow. I think rainforests are pretty cool. And, you know, having sung countless rounds of This Land is Your Land as a child, I was curious to see what the Redwood Forest was all about.

As it turns out, the Redwood Forest isn’t a single forest, but rather a series of national and state parks. Some of them are grander than others, some are more challenging than others (depending on if you want to hike or walk) and they’re fairly spread out. We chose to stop at the Redwood State Park at Skyline Gate based only on proximity, but it was a good choice for us. While the trees weren’t the tallest, the terrain was fairly level, and on a late afternoon, gave us a gorgeous view of the sun streaking in through the trees on it’s way down.

Shop the Haight

Haight Ashbury is one of my favorite streets in the US. Famous for it’s place in history as the origin of hippie culture in the 1960s, the area still exudes that vibe some 50+ years later, with colorful street art, psychedelic store fronts and messages of free love carved into the pavement.

It has modernized (and commercialized) a bit in the decades since the Grateful Dead and Janis Joplin called it home (the intersection proper of Haight and Ashbury streets is currently home to a Ben and Jerry’s ice cream parlor), but it still has that retro nostalgic feel. It gets busy on the weekends (there are some primo restaurants along Haight Street that locals love to brunch at), but if you visit in the morning or on a weekday, it’s much quieter.

My favorite part of the Haight Ashbury district is the shopping. All along Haight Street are secondhand shops with all kinds of cool vintage fashion, décor and accessories, costume shops, cool boutiques and, of course, smoke shops. Each store is different and unique but all have a local flavor you won’t find anywhere else.

Just Take it All In

Whether you’re on a bench at Crissy Field, walking along the Embarcadero, standing under the bridge at Fort Point (my new fave spot to stare at the bridge) or driving through the Presidio, just remember to take a moment and take it all in.

San Francisco is a unique city. A place where love and diversity is embraced and a city that holds an abundance of cool places to explore. Whatever you do, I hope you enjoy it as much as I do!

Have you been to San Francisco? What are your favorite things to see and do?

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