From nearly anywhere in the U.S., you can make the trip to San Francisco for a long weekend (or longer)! In this 48 hour itinerary, we eat Paris-quality pastries, taste Napa Valley wines, and explore dramatic cliffs along the Golden Gate Strait with stunning views of the Golden Gate Bridge.

We left New York on a Thursday night for a weekend in San Francisco. The six hour flight time coupled with the three hour time difference means you land on the West Coast just three hours after you leave! This is great for flying out after a day of work and still arriving early enough to get a sufficient night’s sleep.

We traveled to SF the first weekend in November as fall is often cited as the best time to visit the Bay Area! September is actually San Francisco’s warmest month, with the average temperature peaking around 70 degrees. Although, no matter when you visit, you’ll probably not be greeted with the sunshine you’d expect from California! SF has a mild climate and is known for its wet, foggy air and wind. The first time I visited was in July nearly ten years ago, and one of the only memories that has stuck with me is having to buy a sweatshirt because it was so cold! So, if you’re flexible plan your trip for September or October to have the best weather and also to avoid the crowds that flock to the city in the summer.

After touching down in San Francisco, we hailed an Uber to The Mission, where we’d be staying with a friend who just moved out to SF. If you’re looking for a place to stay I’d definitely recommend Airbnb. If you’ve never tried it, there’s no better place than the city where it was founded (and you can get $40 off your first stay)!

Deciding where to stay in San Francisco can be a bit daunting – as an outsider, it seemed like every few blocks was a new neighborhood! The Mission is SF’s oldest neighborhood but today has some of the city’s newest and most popular restaurants and bars. It’s home to a significant portion of the city’s Latin American community, but has seen an influx of students, artists, and entrepreneurs (including Mark Zuckerberg) over the past decade – which has given it a cultural eclecticism. We were staying on Valencia Street, where you can find local designer shops, tons of cafes, and even more taquerias.

Uber and Lyft are both very popular means of transportation in SF as the metro line, the BART (Bay Area Rapid Transit), is rather limited for getting around San Francisco, better serving as a way to get out to Berkeley and Oakland. Our friends find Lyft to be cheaper on average, but throughout the weekend we’d check both. If you haven’t tried Lyft Line or Uber Pool (ride-sharing services), doing it from the airport is a great first trial as your fellow riders will likely be getting on at the same place! We only paid $24 to get from SFO to the Mission.

If you do arrive to SFO during the BART’s service hours, you can take the train from the International Airport Terminal (connected to the other terminals by the AirTrain), as long as you’re staying along one of the 8 stops the BART makes in SF. Fares on the BART vary by destination, but it should be $8.95 to get downtown.

---

Day One

9 AM : The First of a Few too Many Pastries

Before I started scouring the web for the best breakfast in San Francisco, I had no idea the city was packed with so many bakeries! Being from New York, my go-to breakfast option is a deli bagel sandwich – most often a bacon, egg, and cheese. But in San Francisco, the options seemed to either be bakeries or sit-down restaurants (where I’d be able to get my egg fix).

On our first morning we made our way to Tartine Bakery, a small shop which attracts people to the Mission district on its own. As well-known as Tartine is for its pastries and bread, it is also famed for its line which inevitably spills out of the small storefront. Founded by a husband and wife in 2001, the couple is a perfect match – Liz is the master of pastries and cakes and Chad is the mastermind behind the bread.

We arrived at Tartine around 9 AM on Friday morning to a line of about 20-30 people wrapped around the side of the bakery. To our surprise the line moved quickly, and we were only there for about 20 minutes before we found ourselves in front of the beautiful case of pastries, having to make the impossible decision of what to order. In a time where colorful croissants filled with rainbow cream cheese and milkshakes topped with an entire cookie seems to be filling my Instagram feed, Tartine has stuck to (and mastered) the classics. Having apprenticed in France, Liz and Chad’s baking style is much more European than American.

Between my friend and I, we tried the morning bun, the chocolate croissant and the quiche. The morning bun was the stand-out in my opinion – scented with candied orange and coated with a light cinnamon sugar. As I unraveled the flaky dough, I continually questioned how the outside was so perfectly crunchy and glazed while the inside was so delicately soft – a baking masterpiece! The chocolate croissant was equally as astonishing, with hundreds of layers of perfectly buttery dough. We also ordered a slice of the daily quiche with ham and leek since I’m used to eating eggs with my carbs at breakfast (eggs=energy, right)?! The quiche was surprisingly good, with a delicious flaky pie crust. As we sipped on our coffees and got ready to begin our day, it began to rain and we had to take cover inside the bakery and wait for it to subside – rainy season was beginning!

10 AM : The First of SF’s 220 Parks

San Francisco has more green space that any other municipality in the United States! The number of parks in the city is totaled at 220, and unlike New York’s Central Park, many of these are smaller, only occupying a city block or two. Dolores Park is one of SF’s many parks – located just two blocks away from Tartine in the Mission. If it’s a nice day, bring your pastries to the park instead of wrestling for a table at Tartine!

Upon first glance, Dolores was different than any park I’d laid eyes on, steeply sloping across a few city blocks. The park’s hilly terrain, however, means it provides great views of the surrounding neighborhoods and greater San Francisco. Head to the park’s southwest corner for views of downtown and the rest of the Mission. You’ll see hundreds of dogs running around, and bear in mind if it’s an unusually warm day in SF, every inch of the park will be covered in sunbathers. The park itself is beautiful, with grandiose palm trees and perfectly watered green grass!

10:30 AM : “Hiking” Land’s End

Land’s End is a hiking path in the northwest corner of San Francisco, bordering the channel leading to the Golden Gate Bridge and the entrance to the San Francisco Bay. Land’s End trail has a special allure because of the dramatic cliffs spanning the coastline, separating it from the ocean. Bordering the other side of the trail are towering Cypress trees, shielding the trail from the sun (when it’s out, that is)! It’s hard to believe you’re in a city as you continue along Land’s End, creeping closer and closer to the iconic Golden Gate Bridge.

I put hike in quotations because Land’s End trail is primarily flat, with a couple of sets of staircases, depending on how many lookouts you descend to from the main trail. The views you’ll get along the way are really special, with the Golden Gate slowly getting closer in the distance. This walk was the highlight of our weekend in San Francisco!

We started the hike at the Land’s End Visitor Center. To get there, you can either make your way to Geary Blvd and catch the #38 bus to 48^th Avenue or take an Uber pool as we did! Once you arrive at the Visitor’s Center, you’ll be able to follow the Coastal Trail towards – you guessed it, the coast! Before long, you’ll get your first glimpse of the ocean with the Golden Gate bridge in the distance. We loved how the trail approached the bridge, and stopped every time it re-appeared from behind the trees to snap a picture of it at every angle.

Along the trail you can explore the Sutro Baths, ruins of what was once a large indoor swimming facility, and tons of other detours which lead to awesome lookout points. Don’t miss the Labyrinth, a maze of rocks created by local artist Eduardo Agilera. But I’ll warn you, once you find the Labyrinth, you may never want to leave the overwhelmingly peaceful spot!

The Land’s End path continues east towards the bridge, bringing you towards Sea Cliff, a beautiful neighborhood of SF. We wanted to continue our hike, so we opt-ed to exit the trail at El Camino del Mar, instead of making the round trip back to our starting point. We continued towards the bridge, admiring the neighborhood’s beautiful houses whose amazing backyards are slices of the Pacific’s sweeping cliffs with the Golden Gate bridge on the horizon.

We meandered through the neighborhood for less than a mile before meeting the next coastal trail – Batteries to Bluffs! You can begin this trail at Baker Beach, walking along the beach or on the adjacent trail. At this point, you’ll finally be able to get pics of the bridge with it looking like more than just a dot in the distance! This trail leads all the way from the Sea Cliff neighborhood to the bridge’s many parking lots. As you approach the bridge, don’t forget to look back and admire the neighborhood you just walked through, situated right on the water!

By time we arrived to the Golden Gate Bridge parking area, we had walked about 4 miles and spent two hours admiring the beautiful coast. The walk is one of the more beautiful I’ve done and is not an experience you will find in many metropolitan areas! Like the Land’s End trail, the real difficulty of the Batteries to Bluffs trail is the sheer amount of stairs, but you can elect whether or not you want to explore every inch of the trail or stick to the main route and save yourself some of the incline.

1 PM : Crossing the Bridge (When you Get There)

From the Golden Gate parking area, you can get even closer the the bridge – by now your camera roll will be filled with pictures of it from every distance! If you want to continue your exploration of the bridge, you can also make your way onto it! The bridge’s two sidewalks are split into one for bikers and one for walkers, so unless you have a bike, you’ll need to make your way to the other side of the highway to the East sidewalk (you’ll go through the tunnel beneath the Golden Gate plaza).

Once you’re on the correct side of the bridge, you can decide how much time you want to spend walking across! The total distance of the bridge is 1.7 miles, so you can walk halfway across the bridge and make your way back, or walk the total distance and then call an Uber/Lyft from the other side!

3 PM : Visiting the Times Square of San Francisco

By now you’ve undoubtedly hit your 10k steps, so call an Uber/Lyft from wherever you are and make your way to Fisherman’s Wharf. Here, you’ll find countless souvenir shops, seafood stalls, and of course – rows of fishing boats! Now, we’d worked up an appetite so our first stop was Boudin Bakery for our seafood fix, paired with SF’s iconic sourdough bread!

The verdict is still out on whether or not San Francisco’s sourdough is irreplicable – some claim the city’s climate cultivates a specific type of yeast, others say its been duplicated around the world. Regardless, Boudin has been in business since 1849, so it’s doing something right! Even if you wouldn’t consider yourself a huge fan of sourdough (like me), you’ll need to give it a second chance in its birthplace.

Boudin Bakery is a museum itself, you can lose track of time watching the bakers at work and admiring the adorable bread animals on the shelves! We made our way to the cafe to order the clam chowder in a sourdough bread bowl, seemingly just like everyone else.

We enjoyed the soup on the large outdoor deck next to the restaurant. I have to admit the clam chowder wasn’t the best I’ve had, but I’m a bit spoiled from spending many summers in New England, sampling every clam chowder I could get my hands on. Regardless, it’s hard not to enjoy a sourdough bowl full of creamy chowder, so I’d definitely recommend a stop at Boudin! If the line is out the door, you can also peruse the many other stalls at Fisherman’s Wharf, all of which have their own take on clam chowder and many other seafood classics.

If you want to catch a glimpse of (hundreds of) sea lions, make your way to Pier 39. Here, these mysterious animals have made the many floating docks their personal beach chairs. I got my fill of sea lions a few years ago in the Galapagos, where they were seemingly an invasive species, always occupying the benches lining the sidewalk or lying in the middle of the road stopping traffic. But if you’ve never seen (nor heard) sea lions, they are definitely interesting animals to observe!

You can spend hours wandering around the piers of Fisherman’s Wharf – exploring various souvenir shops and trying a plethora of seafood items, but leave a bit of room in your stomach for dessert! About half a mile from Fisherman’s Wharf is Ghirardelli Square. Once the home of Domingo Ghirardelli’s original factory, the Square is now a lovely assortment of restaurants, shops, and you guessed it – an ice cream and chocolate shop! At the shop you can see the manufacturing equipment, taste a daily free sample of chocolate, and order one of the indulgent sundaes. If you have a few friends in tow you can opt for the Earthquake – eight scoops of ice cream covered in various toppings and hot fudge.

7 PM : Back to the Mission for Dinner (and a Movie)

After shopping our hearts out, we Uber-ed back to our apartment to unload our chocolate and souvenirs. Tonight, we were headed to one of San Francisco’s most popular restaurants – Foreign Cinema!

Foreign Cinema is arguably more well-known for its ambiance than it’s food, but we found both worthy of praise! As the name suggests, the restaurant projects a movie on the back wall of its patio during dinner. There’s lots to look at inside the restaurant in addition to the movie – the space itself is beautiful, with lights strung overhead throughout the seasons.

Even in the winter, the patio offers the best seats in the house as it is partially covered and has plenty of space heaters scattered among the tables. The setup at Foreign Cinema is reminiscent of an upscale drive-in – with small speakers near each table to bring the movie to life.

Both the menu and the movie at Foreign Cinema are on rotation – the cuisine always a selection of seasonal California-Mediterranean dishes. Despite the restaurant’s name, the movie is not always in another language! Before going, you may want to check what movie will be in rotation on the website.

Although Foreign Cinema can be a bit of a splurge with entrees starting upwards of $20, it’s a restaurant unlike any we’d visited before, and we’d definitely go back! Make sure to make a reservation if you plan to visit as it’s not somewhere you can often walk into.

9 PM : Margaritas with a View

It wouldn’t be an appropriate 48 hour guide without a rooftop visit – so once you’ve thoroughly enjoyed your food (and time) at Foreign Cinema, make your way right next door to El Techo, the rooftop bar of Lolinda Restaurant.

On weekends, the line to ascend to El Techo can be quite long, but it moves more quickly than anticipated – and the great view of San Francisco is worth a bit of patience. Grab a drink and take in the expansive skyline!

---

Day Two

9 AM : The Sourdough Tasting Continues

This morning we Uber-ed to The Mill, another one of SF’s popular breakfast spots. Behind The Mill is Josey Baker, who turned his passion for bread making into a bakery, naming it after the piece of equipment he used to grain flour. The Mill is a light and airy space, perfect for Instagram-ing your beautiful toast. It also has a few tables on the street for those who want to dog-watch!

The Mill’s menu offers much more than just loaves of Josey’s many types of bread, including pastries, toasts, and coffee. Among three of us we tried three different toasts – Almond Butter, Seasonal Jam, and Avocado (which seems to have rotated off the menu according to the season). The Seasonal Jam was the fan favorite, and we were imagining how good it would’ve been with almond butter on it as well. When I find myself in SF next, I’ll definitely ask if they can make that combination happen!

10 AM : On the Scene of “Full House”

From The Mill, it’s just a one block walk to Alamo Square Park! Alamo Square is one of the larger parks we explored within SF, occupying four city blocks. Like Dolores Park (and the rest of SF), it’s a hilly park – which means it has great views of the surrounding city at its highest points.

“Full House” was one of my favorite shows growing up, so I knew I had to go check out the houses from the opening scene of the show, known as the Painted Ladies. This group of Victorian houses stands out due to its tight formation, colorful facades, and primarily – its beautiful backdrop of the surrounding city. Head to the east border of Alamo Square Park for a postcard-worthy photo of these SF icons! Maybe if you’re lucky John Stamos will photo-bomb…

11 AM : A Street Car Named Powell-Hyde

Okay – technically this a cable car, but close enough! For another classic San Francisco experience, make your way towards Union Square (the intersection of Powell & Market Streets), where you can board one of the city’s cable car lines! SF was the first city in the world to introduce cable cars (in 1873), and it’s now the last to have them in operation.

While there were once 23 cable car lines throughout the city, there are now only three routes remaining. Powell-Hyde is often cited as the fan-favorite line because of its views, travelling through the beautiful Russian Hill neighborhood and by the top of Lombard Street before steeply descending towards the bay. Union Square is about two miles from Alamo Square Park, so it’s up to you whether you’re up for the walk or would rather call an Uber.

Since cable cars can’t go in reverse, they always require a turnaround point, which happens to be Union Square for two of the lines! Here, you’ll be able to see the operators hop out of the car and turn it around on the revolving wooden platform.

A ticket for the cable car costs $7/person and can be purchased in advance at one of the ticketing booths or on board the car with cash. Unfortunately, it is only valid for one ride, so if you get off the car, you’ll have to buy another ticket to re-board, even along the same route.

Since Union Square serves as the turnaround point, it often has lines to board the cars. But, it will be worth the wait to get one of the best seats in the house. If possible, you’ll want to be on the right side of the car for the best views (if you can get the front pole, that’s an added bonus)!

After twenty minutes, we hopped off the cable car at the Hyde and Lombard stop. From the top of this hill, you’ll notice great views of the surrounding neighborhoods – and in the distance you’ll be able to see the Bay Bridge and Coit Tower. You won’t be alone at this stop, as this is another one of SF’s postcard-worthy spots.

1 PM : *One of* the Most Crooked Streets in San Francisco

By now you’ve surely noticed how steep the streets of SF are, but you may not have seen one as crooked as Lombard Street! This section of the street is actually as crooked as it is because of its steepness! In the 1920’s, people feared Lombard Street for its incline and created switchbacks in the road to increase safety (and added aesthetic appeal in the process).

Now, Lombard Street isn’t actually the most crooked street in SF – that honor belongs to a section of Vermont Street in the Potrero Hill neighborhood. However, Lombard Street attracts all the visitors due to the beautiful homes which grace its sidewalk (some of the most expensive real estate in the city) and the colorful flowers which bloom in the spring and summer in the grassy patches between the eight curves.

Take a few pictures of Lombard Street from the top, then you can make your way down one of the staircases located on either side of the street.

1:30 PM : Double Double, Animal Style

From the bottom of Lombard Street you can walk back to Fisherman’s Wharf in about ten minutes. Luckily – you’ll be making your way toward sea level and won’t be climbing your way through the Russian Hill neighborhood.

If you often find yourself in the middle of the classic West Coast vs. East Coast, In-N-Out vs. Shake Shack debate (as I do here in New York), you’ll need to try the famous California burger for yourself. If you have no idea what I’m talking about, you still may want to see for yourself why this fast food chain has a cult following on the West Coast.

Despite being a CA staple, the only In-N-Out in SF can be found at Fisherman’s Wharf. On the inside, almost all In-N-Out’s look the same – a classic 1950’s red and white style diner with booths and smiling employees whose outfits match the decor. You’ll pretty quickly notice In-N-Out has a very short menu. Unlike its East Coast counterpart, In-N-Out doesn’t have multiple types of burgers to choose from, nor does it have chicken or mushroom burgers or hot dogs.

Despite only having five different lines on its menu, In-N-Out does have a (not so) secret menu, which it describes as coming about from customer’s unique ordering preferences. If it’s your first trip to In-N-Out, a classic order is the Double-Double: two patties with cheese, lettuce/tomato/onion, and In-N-Out’s classic sauce (often compared to Thousand Island dressing) with Animal Style Fries: classic french fries topped with melted cheese, grilled onions, and that same delicious, orange sauce.

Again, there are lots of ways to customize the short menu – including the 3X3 or 4X4 if you’re feeling ambitious and want a burger with three or four patties (and corresponding cheese slices). In-N-Out definitely beats Shake Shack on the affordability scale, its much cheaper than its East Coast counterpart  – the Double-Double is less than $4 and a plain order of fries is less than $2!

Personally, I use every trip to California as en excuse to indulge in a burger and (cheese-smothered) fries. Although some may say I’m biased, I have to say I prefer Shake Shack’s burgers, but not much compares to those Animal-Style fries….

3 PM : Taking the World’s Second Best Ferry Ride

You read that right – The Society of American Travel Writers ranked the ferry ride from San Francisco to Sausalito the second best in the world back in 2009! This is an instance where we can safely say the journey is as exciting as the destination!

Sausalito is a small town in Marin County, located across the Golden Gate Strait, just over four miles from San Francisco. Many of the town’s homes are situated on its steep hillside overlooking the bay, giving it the feel of a seaside town in the Mediterranean.

There are two ferries which service Sausalito from SF, Golden Gate Ferry and Blue & Gold Fleet. If you’re making the trip from In-N-Out or the Fisherman’s Wharf area as we were, you’ll want to take the Blue & Gold Fleet ferry as it leaves right from Pier 41! The schedule changes by season, so make sure to check the website for the most up-to-date timetable. If you’re coming from elsewhere in SF, you can also take the Golden Gate Ferry departing from the SF Ferry Building. The ride to Sausalito is about 30 minutes and costs $12 each way.

When the ferry departs SF, you’ll want to be at the back of the boat to see the magnificent views of the city from the Bay. The boat will also pass by Alcatraz Island, home of the infamous abandoned prison. Soon you’ll also get more great views of the Golden Gate bridge! As you approach Sausalito, head to the front of the boat for your first view of this charming town!

Once you’ve arrived in Sausalito, walk along the town’s main street, Bridgeway, to take in the great views of SF in the distance. Along the way, you’ll be tempted to stop in the many souvenir shops, art galleries, and clothing stores. If you’re up for a bit of a walk, you can also check out the Sausalito houseboats, many of which are located by Gate 5 Road, about 1.5 miles from the port of Sausalito.

These floating homes date back to the end of World War II, when returning veterans and (eventually) artists and musicians inhabited the many abandoned vessels. You can walk along many of the docks (Liberty Dock, Issaquah Dock, South 40 Dock and Main Dock) to check out these communities of boats. You’re sure to see some beautiful boats that look more like impressive homes than abandoned ships!

5:30 PM : A Taste of Napa without the Drive

After spending a few hours walking around Sausalito, we were ready to sit down and try some Napa Valley wines! Madrigal Family Vineyard has a tasting room right on Bridgeway in Sausalito, where you can taste wines right from the vineyard in Napa.

The tasting menu is $25 (much cheaper than any in Napa itself!) and includes five different high-quality wines. We really enjoyed the selection, and I was a huge fan of the 2015 Tempranillo, a medium-bodied estate red. We also learned a lot about the family-run vineyard, which has been passed down through three generations and is now run by the founder’s grandson.

After enjoying another glass at Madrigal, we headed back to the ferry and arrived in SF half an hour later!

Alternatively, another option for this afternoon would be to visit Alcatraz Island. Exploring the penitentiary and taking the audio tour definitely makes for a fascinating few hours! Since Alcatraz is reached by ferry, you’ll also still get the same great views as you would on the trip to Sausalito. If you’re interested in visiting Alcatraz, ensure you book your tickets in advance as they definitely sell out! 

7:30 PM : Life-Changing Mexican in The Mission

Having passed by a plethora of taco joins over the past few days in our new home, we were set on having Mexican for our last dinner. Almost unanimously everyone recommended El Farolito – we were sold! From its looks, El Farolito is an extremely unassuming spot, but its relatively constant line is the first indicator that its not just another Mission taco joint.

I ordered the Super Suiza quesadilla, which was stuffed with cheese, steak, sour cream, and avocado (all for $7.75)! As the cashier handed me my bag, I actually thought it was both my friend and I’s meals – it was that heavy! The multiple recommendations we got for El Farolito didn’t even do it justice – definitely the best quesadilla I’ve ever had! I still dream about the day I make it back to SF to get it again. It’s for the best that I don’t live in SF because I would be tempted to come to El Farolito weekly….

I’d definitely recommend making the trip to El Farolito, but keep in mind it’s a very casual spot. It’s counter service, cash only and most of the seating is in old wooden booths, so it’s not for everyone.

If you’re looking for a bit more upscale of a dining option, Sugoi Sushi is another great spot in The Mission! It has great sushi, delicious gyoza, and a hip dining area where you’ll enjoy all this food.

We headed back to our apartment – extremely full and ready to detox after our two days of pastries, burgers, and quesadillas. Since you lose three hours when flying from west to east, it’s not uncommon to take a red-eye home, but we weren’t until leaving bright and early the next morning.

Still full from our quesadilla the night before, we Uber-ed back to SFO the next morning to make our way back to the land of Shake Shack.