How to Spend 4 Days in San Francisco

San Francisco is one of those places I have always wanted to go to but have never found an opportunity. Finally, I got that opportunity to spend 4 days in San Francisco and planned a trip with my mom. Originally, we were thinking two days in the city and two days in the Napa Valley area. However we went shortly after fires devastated the Napa area. So we decided two days south of San Francisco was a good alternative. And we were right!

Disclaimer: This post may contain affiliate links so if you make a purchase or booking through one of our links we might earn a small commission (but don’t worry, it’s no extra cost to you).

Lodging

San Francisco is an expensive city and that includes lodging. When planning where to stay, you can find cheaper options outside the city. However, we ultimately decided we would splurge on a hotel in a prime location because we were only in the city for two days. We stayed by Fisherman’s Wharf.

Transportation

In addition to the expensive hotels, the costs to park your car in the city are astronomical. Since we did not need a car in San Francisco, we opted not to rent one for the first two days. Instead, we walked, bussed, ferried, and Uber-ed.

However, we would need a car for the last half of the trip. Near Fisherman’s Wharf, we rented a car from Hertz and returned it to the airport when the vacation was over.

DAY 1 – SAN FRANCISCO

Lombard Street

Before our morning tour to Alcatraz, we had some time to kill. So we walked to Lombard Street, and I got my first taste of the famous San Francisco hills. The walk up Russian hill got my blood pumping. At the top of the hill was Lombard Street, which is well-known because of it’s steep, hairpin turns.

Alcatraz Island

The tour to Alcatraz Island is a must-do activity in the Bay City so you can see first hand the life of the prisoners that were incarcerated at The Rock. The tour begins with a ferry ride from the mainland to the island. Then we watched a short video before touring the prison. There are various tour options, so make sure you check them all out.

Boudin Bakery & Café

Boudin Bakery has been a San Franciscan staple since 1849. This flagship shop on Pier 59 has an area where they sell various bread products including their legendary sourdough. They also have a café where we ate clam chowder in a bread bowl for lunch. It was so good, we came back the next day for more.

Ferry to Sausalito

After lunch, we hopped on a ferry to Sausalito. Sit back and relax as the boat ride takes you to Sausalito after making two other stops. Take time to look inside the cute shops of Sausalito!

Sausalito to Golden Gate Bridge

If you are in the mood for some exercise, walk the 4.2 mile trek from Sausalito to Golden Gate Bridge during your 4 days in San Francisco. Walk along the bay shores, past Fort Baker, and up the steep hill just under the head of Golden Gate Bridge. I advise you map the route before you go, or follow Google Maps in real-time. At the top of the hill visit the Golden Gate Bridge View Vista Point for excellent views of the bridge and the city.

Cross the Golden Gate Bridge

Crossing the 1-mile suspension bridge was more difficult than the walk from Sausalito. It is like walking through a hurricane-strength wind tunnel, and it almost blew us away.

Ghiradelli Square

From the San Francisco side of the bridge, give your feet a break and catch a bus to Ghiradelli square. Check out the area and have dinner. Inside the Ghiradelli store, we bought tons of chocolate to eat throughout the trip. After walking 27,387 steps for the day, we treated ourselves to sundaes at Ghiradelli. So yummy!!

DAY 2 – SAN FRANCISCO

Breakfast at Mama’s

At 7am, we caught an Uber to Mama’s on Washington Square, which doesn’t open until 8am. We were the 10th people in line at the popular breakfast spot. The food was exquisite, and I highly recommend the breakfast sandwich. This restaurant only accepts cash and debit card so plan accordingly.

Chinatown

Next we walked off our breakfast with a half-mile stroll to the infamous San Francisco Chinatown. We stopped in the Golden Gate Fortune Cookie Factory, which was not a typical factory. Inside the doorway, four or five women were folding the cookies by hand. I would have been disappointed but they gave us a grocery sack full of defected cookies for free!

Walk to Union Square

I hope you wore your walking shoes because you’re about to walk ’til you drop. The total distance for the next part of today’s journey is only a mile, but the steep ups and downs of the hill makes it a challenging walk. Hike up the famous Nob Hill, and check out the lobby of the Hotel Fairmont. From here walk downhill past Huntington Park to Grace Cathedral. Finally end your trek at Union Square.

Castro District Rainbow Colored Crosswalk Intersection

Next we took an Uber to the Castro District to see the sea of rainbow flags, paintings and crosswalks. Gay pride is highly celebrated in this San Francisco neighborhood.

Painted Ladies

We continued the theme of the day, walking, with a 1.2-mile jaunt to the Painted Ladies. Here, we sat at Alamo Square Park across the street and marveled at the row of Victorian houses made famous in “Full House.”

Japanese Tea Garden

After we felt rested, we caught an Uber to the Fine Arts Museums of San Francisco where we ate a late lunch. We opted to enter the Japanese Tea Garden nearby. An easy stroll through this botanical garden is what we needed after a long day of walking.

Cable Car

We headed back to Fisherman’s Wharf, via Uber, to the first Cable Car Stop on Mason. We’re in San Francisco, so we had to ride in a cable car while here. We took the Powell/Mason line to the end and all the way back just for fun.

Fisherman’s Wharf

We spent the rest of the night walking around Fisherman’s Wharf shopping and people watching. Then, we ate dinner at Boudin Bakery for our second helping of clam chowder. Don’t judge me! I love clam chowder and have only eaten it when vacationing in Boston or San Francisco.

DAY 3 – SAN FRANCISCO

Googleplex

If the theme of the first two days was walking, then the theme of the next two is driving. We left San Francisco driving south towards Googleplex. On the way, we saw a sign for Stanford University so we made a short detour and drove through the campus which was beautiful. There is not really anything to do at Googleplex, but we wanted to see it. We lucked out and found some Google bikes left outside, so I took one on a joyride.

Winchester Mystery House

The Winchester Mystery House in San Jose is a must-see attraction during your 4 days in San Francisco. It was once the residence of Sarah Winchester, the heir of the Winchester firearm fortune. She believed the house was haunted by all the people killed by Winchester guns. The only way to appease the ghosts was to never stop construction on the house, 24 hours a day, seven days a week. The house has several architectural mysteries like stairways that lead to no where and second-floor doors that open to the outside with no landing or stairs, just a drop-off.

Pebble Beach Golf Course and 17-Mile Drive

Our next stop was the Pebble Beach Golf Course. We perused the golf and gift shops, and then walked to the 18th hole where golfers were making their last putts of the day. Next, we started the 17-mile drive in and around Pebble Beach. We made several stops along the way looking at the beautiful golf course on the beach. I don’t play golf, but I would play here!

Big Sur

The events of the day took less time than we expected, so we added a drive south on the Pacific Coast Highway to Big Sur. We pulled off the road at two stops: Bixby Creek Bridge and McWay Falls, in Julia Pfeiffer State Park. The Pacific Coast Highway drive was stunning with the mountains on one side and the beach below. Make sure to check the status of the road in this area before traveling here. Often mudslides cause washouts and road closures.

Cannery Row in Monterey

We drove back north to Monterey where we stopped at Cannery Row for dinner. The area was crowded with people shopping and having dinner. We decided to be the ultimate tourist and eat at Bubba Gump Shrimp Co.

DAY 4 – SAN FRANCISCO

Henry Cowell Redwoods State Park

Before heading north to the Santa Cruz area, we drove by the Point Pinos Lighthouse. We entered the Henry Cowell Redwoods State Park in the Santa Cruz Mountains for a walk through the giant trees. The Redwood Loop Trail was an easy 0.8-mile hike to get the blood pumping. This trail is a perfect way to get outdoors during your 4 days in San Francisco.

Santa Cruz Boardwalk

Next we walked along the Santa Cruz Boardwalk where admission is free. Each attraction costs to ride or play, but we did not ride anything while there. Then, we strolled along the shoreline to get a panoramic view of the iconic Boardwalk and Giant Dipper, a historic wooden roller coaster. We walked out on the Santa Cruz wharf for views of the sea and to eat lunch.

Shark Fin Cove

About 20 minutes north of Santa Cruz on the Pacific Coast Highway you will find Shark Fin Cove. From the parking lot, you will cross train tracks and then shimmy down a very steep, narrow opening. Once at the beach, you will have a close of view of a rock island in the shape of a shark fin. Watch the waves as they crash into the cliffs beside you.

After climbing to the top of the hill, walk along the ocean cliffs for epic views of the waters on the horizon. After you get your fill of the cliffside views, drive back south to Capitola.

Capitola

Capitola is a quaint town with beachside restaurants and shops. But the highlight of this town is the colorful rows of housing units located right on the beach. Take time walking in the sand and taking in the sights of the vibrant hillside homes.

West Cliff Drive and Lighthouse Point

We walked along West Cliff Drive along the shores of Monterey Bay to Lighthouse Point. Inside the light house is a small museum dedicated to surfing history. Right outside the lighthouse is a viewing platform on the edge of ocean cliffs where you can watch dozen of surfers catching waves.

Natural Bridges State Park

Next we drove to Natural Bridges State Park during our 4 days in San Francisco and walked onto the beach. After millions of years of water erosion, the sea carved the Natural Bridge out of the existing cliff and carved an arch in the middle. We watched an incredible sunset from this beach, and then we drove to our hotel located near the San Francisco airport. Sadly, our flight was early the next day.

Four days to explore San Francisco to Big Sur is an aggressive itinerary but a great plan if you want a taste of this area. To fully discover each of these areas, I suggest spending more time here.

You May Also Be Interested In

How to Spend 3 Days in Yosemite National Park

How to Hit the Highlights in 1 Day at Sequoia and Kings Canyon National Parks

Perfect Long Weekend Trip to Las Vegas

8 Amazing Bridges to Build a Vacation Around

3 Days in New York City: How to Maximize Your Time in Manhattan