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How to Spend a Long Weekend in San Francisco

San Francisco has a variety of districts and neighborhoods, each offers a unique flavor that makes up SF. While you may not be able to hit every neighborhood, this guide will give you the best hotspots if you only have a long weekend in the city!

how to spend a weekend in San Francisco #jjadventures

Did you read my Tips Before Going to San Francisco? Check it out here!

Day 1

Dolores Park

Dolores Park is in one of the hippest neighborhoods in San Francisco, The Mission. It provides the perfect spot for locals to get outdoors, chill, and with a variety of activities on the 16-acres, it attracts thousands of people on a gorgeous San Francisco day.

Check to see if there’s an event or festival when you visit, but if not, pack a picnic, lay in the sun, and enjoy the city’s skyline views. In the mood for a bit more of an active park adventure? Catch a game of soccer, basketball, or a tennis match.

Dolores Park | How to Spend a Long Weekend in San Francisco #jjadventures

Alamo Square

You can’t visit SF without saying hi to the cast of Full House haha for the best photo opp of the famous Painted Ladies (and to minimize disruption of angry homeowners that are SO over tourists) head to Alamo Square.

Alamo Square | How to Spend a Long Weekend in San Francisco #jjadventures

Haight-Ashbury

Find your own Summer of Love in the Haight-Ashbury neighborhood. The Haight has a unique charm and history of the birthplace of hippies in the 60’s. You’ll find vintage shops, record shops, the Grateful Dead house, quirky cafes, pubs, and bookstores here.

Golden Gate Park

Did you know Golden Gate Park is 20% bigger than Central Park in NYC? You could definitely spend an entire day+ here doing everything. If you’re limited on time, pick 1 or 2 attractions to check out:

  • Japanese Tea Garden
  • de Young Museum
  • California Academy of Science
  • Windmill and Tulips
  • Conservatory of Flowers
  • Carousel
  • Children’s Playground
  • Botanical Gardens
  • Strybing Arboretum
  • Stow Lake & Strawberry Hill
  • Aquarium
  • Rose Garden
Golden Gate Park | How to Spend a Long Weekend in San Francisco #jjadventures

It’s always nice to just wander around parks at your own pace but if you’re trying to squeeze in a bit more education, then I suggest taking a walking tour or renting a segway or bike to get around faster and see more of the park. The path towards the far west end of Golden Gate Park will drop you out at the Pacific Ocean. If you’ve timed it perfectly, you’ll arrive just in time to catch happy hour oceanfront.

Happy Hour with a View

The Cliff House has the perfect backdrop for enjoying some tapas and a cocktail; the Pacific Ocean! The Bistro does not take reservations, while both the Terrace Room and Sutro’s suggest making a reservation. However, I’ve always just walked in and sat in the bar area for happy hour with no wait!

The menu changes every once in a while but everything is always fresh and delicious especially the seafood! Highly recommend their mules ๐Ÿ˜‰

Sutro Terrace Room | How to Spend a Long Weekend in San Francisco #jjadventures

Land’s End Trail

The Land’s End Trail is a little over 3 miles with stunning views of the Pacific Ocean. There are many parts of the trail that shoot down the rocks to a beach or over put you out on a cliff overlooking the Pacific Ocean. Here you’ll also find the secret Labyrinth at Lands End. It is located on a cliff and you have to carefully climb down steep rocks to get it. The Lands End Labyrinth has been destroyed a few times but each time, the artist- Eduardo Aguilera rebuilds it.

I’ve walked many Labyrinths but this one is by far my favorite as you can feel the ocean breeze and mist from the waves as you walk on the outer edge closest to the cliff. It’s quite tranquil here especially if you’re lucky enough to get it all to yourself!

Labyrinth Lands End Trail | How to Spend a Long Weekend in San Francisco #jjadventures

Late Night Munchies?

There’s no way to visit California and not go to In-N-Out Burger at least once!

double-double burger #jjadventures

Day 2

Get Baked in SF

Stand in line for a famous cruffin from Mr. Holmes Bakehouse! Opening at 7-am on weekdays and 8-am on weekends, I suggest arriving 30-minutes early to ensure you get the freshest cruffin. Plus, it’s part of the experience; maybe you’ll meet a new local friend to have an adventure with (highly recommend if you’re traveling solo)!

Get Baked at Mr. Holmes Bakehouse | How to Spend a Long Weekend in San Francisco #jjadventures

Cable Car Museum

A trip to San Francisco wouldn’t be complete without riding a charming cable car up a steep hill. But before you hop on, delve deeper into the history of this beloved transportation system at the Cable Car Museum. Located at 1201 Mason Street in the heart of Nob Hill, the museum is housed in the historic Washington-Mason powerhouse and carbarn, the very engine that keeps the cable cars climbing to this day.

The Cable Car Museum exhibits take you on a journey through the fascinating history of San Francisco’s famous cable cars, from their invention in the 1870s to their present-day operation. You’ll see antique cable cars, including the oldest operating grip car in the world, learn about the mechanics of the system through interactive displays, and even peek into the working powerhouse through a glass viewing tunnel.

Admission is free and it’s open every day except major holidays, from 10:00 am to 5:00 pm. After your visit, you’ll have a newfound appreciation for these iconic San Francisco symbols as you hear their clanging bells and feel the pull of the cable beneath your feet.

Authentic Chinatown

San Francisco possesses North America’s largest and oldest Chinatown. Past the Dragons Gate (shown below), enclosed in these 24 blocks is a community with its own identity, customs, language, and culture. The streets are always bustling with street vendors. Lined with traditional Chinese bakeries, teahouses, jade, herbalists, boba, souvenir shops, modern and traditional boutiques, and of course KTV!

Explore China Town | How to Spend a Long Weekend in San Francisco #jjadventures

Many restaurants cater to western Chinese but step out of your comfort zone and get in on some of the authentic cuisines! After returning from living in China for 3 years, I found my cravings at an all-time high for authentic Chinese.

Here are a few of my favorites:

  • Good Mong Kok Bakery
  • Golden Gate Bakery
    • Egg tarts 蛋挞
  • Chong Qing Xiao Mian (Sichuan)
  • Peninsula Seafood Restaurant (Cantonese, Dim Sum)
    • I’ll add that this place has awful reviews but as I read them, I realized it’s because people were expecting western Chinese food. SPOILER ALERT: Kuang Pao Chicken is not even a dish in China 😂
  • Bund Shanghai (Shanghainese)
    • Xiao Long Bao 小笼包
  • Sam Wo Restaurant (Cantonese)
    • Wonton 馄饨
  • Hunan Home’s Restaurant (Hunan)
    • Hunan Chicken 湖南鸡

**Please note that most authentic Chinese restaurants have different standards than Western restaurants you’re used to. Yes, they all speak Chinese but they do speak English to customers, shouting and raising your hand for service is not only expected but REQUIRED! If you’re the only foreigner 老围 in the restaurant then you’re probably in the right place!

Coit Tower

Walking up to Coit Tower is a *steep* journey but the neighborhood is so lovely and the steps will allow you to burn off all the delicious food you’ve eaten in San Francisco!

Admission to go up is under $10 and provides 360° of the Bay Area. The lower interior is filled with murals by artists of the Great Depression portraying life from the 20’s and 30’s in SF.

I love Coit Towers’ history; it was made in honor of Lillie Hitchcock Coit who came to San Francisco before California was even a state. In the 1800s, she was “odd” for her time…read more of her story here. Her will stated that 1/3 her estate ($225,000 in 1929) shall be used to add “to the beauty of said city which I have always loved.” Coit Tower was built, along with a statue of a fireman holding a woman in his arms to represent her love and belonging to No. 5.

Coit Tower | How to Spend a Long Weekend in San Francisco #jjadventures

Fisherman’s Wharf

Fisherman’s Wharf is home to Ghiradelli Square, the famous Pier 39 (& most importantly the sea lion colony at Pier 39), Aquarium of the Bay, Ripley’s Believe it or Not Museum, Wax Museum, San Francisco Maritime National Historical Park, National Historic Landmarks like the SS Jeremiah O’Brien and USS Pampanito (a 19th-century cargo ship from World War II-era), and the Cannery Shopping Center.

There is always live street entertainment along the streets and boardwalk, people-watching is key, and if you love seafood there is plenty to choose from. Restaurants range from 3rd-generation family restaurants like Alioto’s Restaurant and Fog Harbor Fish House to chains like Bubba Gumps and In-N-Out. 

All boats and tours out of SF leave from Fisherman’s Wharf.

Pier 39 + Fisherman's Wharf | How to Spend a Long Weekend in San Francisco #jjadventures

Alcatraz Island

Alcatraz Federal Penitentiary was a maximum-security federal prison on Alcatraz Island operating up until 1963. Due to the island’s location in San Francisco Bay with cold waters and strong currents as well as the high security on the island, it was thought to be escape-proof.

Spoiler alert: it wasn’t!

Some of America’s most dangerous felons were housed here including the “Birdman” Robert Franklin Stroud, Al Capone, George “Machine Gun” Kelly, Arthur R. “Doc” Barker, Alvin “Creepy” Karpis and many more.

The prison staff, as well as their families, also lived on the island…not my idea of #islandliving.

Today, Alcatraz is a public museum and one of SF’s most popular tourist attractions. Grab a ticket from Fisherman’s wharf; tickets include a boat ride over and a tour of the island, cells, and audio narration from former inmates, guards, and rangers. The narrations by former inmates while walking through the eery prison blocks sends chills down my spine. Details about life here by inmates, guards, and even their families along with the numerous prison escape attempts will leave you brimming with knowledge.

Alcatraz Island | How to Spend a Long Weekend in San Francisco #jjadventures

SF’s Hottest Rooftop

Wind down from the day at SF’s hottest rooftop named one of “The Best Rooftop Bar in the U.S.” by Condé Nast Traveler.

Charmaine’s Rooftop Bar & Lounge at San Francisco Proper is surrounded by endless views and best yet; it’s weatherproof! As you arrive 120 floors above SF, you’re transported to a chic terrace with laid-back California vibes.

The indoor area features a few different rooms, each with its own service and style. The main lounge has a bar with a seating area of uniquely designed chairs, couches, lamps, and tables. High sliding glass doors sprawl out onto the patio on a gorgeous day. During the cooler or wet season, doors are closed while the fireplace provides a cozy atmosphere. Outdoors you’ll find chic chairs and couches gathered around rock-enclosed firepits to keep warm, and low and hightop tables.

Check out SF's Hottest Rooftop Bar | How to Spend a Long Weekend in San Francisco #jjadventures
No photos made it out from this bar-hopping night with new friends but a screengrab from a silly video

A full bar with cocktails going for $16, beers ranging from $7-14, and wine and bubbles by the glass at $13 or bottles ranging from $80-400. Snacks include olives, nuts, a cheese board, salads, sliders, fries, quesadillas, and Crudités.

Day 3

Themed Brunch

Friends with Benedicts at Chief Sullivan’s is an experience to say the least. Chief Sullivan’s is an Irish Pub that hosts Friends with Benedicts Pop Up (check out their site here for other locations popping up in the city). Known for their benedicts, pancakes, and themed brunches; yes, you heard that right…THEMED BRUNCHES!

The brunch themes typically last a month with themes like FRIENDS, Scottish, M. Night Shyamalan, Game of Thrones, Harry Potter, 70’s, The Jungle Book, Super Heroes, and currently South Park.

**I attended the Game of Thrones brunch at Friends with Benedicts**

Friends with Benedicts | How to Spend a Long Weekend in San Francisco #jjadventures

The Palace of Fine Arts

The Palace of Fine Arts was originally constructed to exhibit and present artwork for the Panama-Pacific Exhibition in 1915 and now remains as a popular venue for weddings, galas, tradeshows, and corporate events. Its exterior is popular for photoshoots as the exterior grounds are magical; every time I visit I see someone taking wedding photos or engagement photos.

Palace of Fine Arts | How to Spend a Long Weekend in San Francisco #jjadventures

Rent a Bike

Rent a bike at Golden Gate Bridge Bike Rentals and experience the ride over the famous Golden Gate Bridge. It’s roughly 2 miles from side to side, so it’s quite a quick cycle there and back or you can grab the ferry back. However, across the bridge in the charming little coastal town of Sausalito, you’ll find plenty to keep you busy. Explore the last of the eclectic houseboat communities from the free love 60’s, the Real Napa offers a taste of wine country, or get your knowledge on at the Marine Mammal Center or U.S. Army Corps of Engineers Bay Model.

Hike Marin Headlands

Catch a different view of the city across the Golden Gate Bridge from San Francisco in the Marin Headlands part of the Golden Gate National Recreation Area. The Marin Headlands is home to a number of historic military settlements and fortifications with several bunkers, batteries, and the SF-88 Nike Missile silo which is open for tours on Saturdays.

Some points of interest I recommend:

  • Kirby Cove
  • Point Bonita Lighthouse
  • Battery Spencer
  • Golden Gate View Point
  • Tennessee Valley
  • Hawk Hill

**dependent on activity level and time

Hike Marin Headlands | How to Spend a Long Weekend in San Francisco #jjadventures

If you’re really not interested in biking over the Golden Gate Bridge or hiking around the Marin Headlands but still want to experience the Bay Area from a different perspective there are still many other options! Hire a boat for an afternoon on the bay to see the Golden Gate Bridge from a different perspective and learn some interesting facts.

Opt out of physical activities or add an extra day with a boat tour

Captain Kirk's San Francisco Sailing Boat Tour | How to Spend a Long Weekend in San Francisco #jjadventures

Captain Kirk’s San Francisco Sailing offers sunset cruises, sailing lessons, special events-birthdays, weddings, corporate client entertainment, corporate team building, and ash scattering.

My family and I used Captain Kirk’s San Francisco Sailing to spread my mom’s ashes in the Bay. While this may not apply to most people’s visit to SF, I would still highly recommend a boat tour with Captain Kirk. We were honored to have Captain Kirk as our captain but all of the captains and crew are amazing!

Although the reason for our trip was extremely emotional and difficult, the experience my family and I had with Captain Kirk and crew was delightful. They were so respectful and kind during the moments of scattering my mom’s ashes. We spent a few more hours out on the boat and although my family and I have spent a lot of time in the Bay Area, Captain Kirk has a wealth of interesting knowledge to share! They’re personable and helpful; I was just so overwhelmed with how well they managed the entire day.

October is so beautiful in the Bay Area it was such a lovely day to be on the water. We were even able to see seals hanging out and porpoises jumping out of the water and surrounding us all day, it was quite a surreal experience. Of course, this is not guaranteed but the level of service and experience are!

I cannot recommend Captain Kirks San Francisco Sailing enough.

Mexican or Italian?

Nopalito has that authentic Mexican vibe with a California twist. Typically there is a wait because they are busy and the venue is small but in SF it’s worth the wait.

Recommendations to order:

  • Ceviche
  • Pescado Tacos
  • Totopos con Chile
  • Strawberry Lemonade
  • Strawberry Almond Horchata

Tony’s Coal-Fired Pizza and Slice House is one of the only West Coast pizzerias offering New York-New Haven-style pizza. There is a separate Slice House on Market Street and neighboring Slice House and Tony’s Pizza Napoletana on Stockton. All are owned by 13x World Pizza Champion, Tony Gemignani.

The Slice House is quite small and usually has a variety of 6 per day, whereas Tony’s Coal-Fired Pizza has a full menu with gluten-free options and indoor-outdoor seating.

Recommendations to order:

  • Sweet Grandma (extra sweet tomato sauce, garlic, oregano, aiello mozzarella, pecorino, basil)
  • Double Fratellanza (pepperoni, mushrooms, mozzarella, sausage, salami, romano)
  • Sausage and Stout (honey malted stout dough, mozzarella and beer sausage, beer salt, caramelized onions, fontina cheese, crushed red peppers)
  • Brooklyn Calzone (ricotta, spinach, mozzarella, garlic)

Want to extend your trip? Here are a few other ideas of things to do in San Francisco…

Ride the famous San Francisco Cable Car

Ride the famous San Francisco Cable Car | How to Spend a Long Weekend in San Francisco #jjadventures

Root for the Home team at a San Francisco Giants Baseball Game

Take in 360° views of the Bay Area at Twin Peaks

360° Views at Twin Peaks | How to Spend a Long Weekend in San Francisco #jjadventures

Lombard Street

Swerve down Lombard Street, the famous twisted street known for its hairpin turns and insane traffic. If you didn’t rent a car –it’s also fun to walk down Lombard and watch cars drive down it.

Swerve Down Lombard Street | How to Spend a Long Weekend in San Francisco #jjadventures
Looking for more weekend getaways? Check out my posts below!
Best things to do outdoors in San Diego #jjadventures
3-day itinerary for Bellingham #jjadventures
Oktoberfest in Leavenworth, WA #jjadventures
A Guide to a Weekend Getaway on Orcas Island #jjadventures
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