My Perfect San Francisco Solo Travel Itinerary

Day 2, San Francisco Spontaneous Solo Travel Day

My San Francisco view from the Kensington Park Hotel

I loved visualizing, planning and packing for my combination solo travel and sister trip adventure to San Francisco and the Giant Sequoias. Now, after a very full arrival day and a really good night’s sleep at the Kensington Park Hotel, I was ready for my first full solo day in San Francisco. I might as well admit it. I’m not a morning person. But I made a discovery about the Kensington’s amenities that really made my morning flow. There are elegant little self-serve stations with coffee and biscotti. (I can’t really even begin to tell you how happy this made me). Best of all, I didn’t have to go to the lobby, I just padded down one flight of stairs and there they were. There were no lines, so I just piled (quite a few) biscotti on my plate, poured coffee into my lovely ceramic cup and enjoyed them in my room. A perfect way to start the morning. After taking in the view of the city, I was ready to start the day!

Embracing Mindful Wandering

My first stop was the front desk to load up my tote bag with maps and brochures and ask lots of questions — always a good plan! I didn’t really have specific destinations in mind. I knew I wanted to ride a cable car, find my way to Haight Ashbury, and visit the San Francisco Museum of Modern Art in the evening; as for the rest, I embraced mindful wandering. My favorite way to explore when traveling solo. I know wandering isn’t for everyone, so feel free to use my “spontaneous itinerary” in this post and the wrap-up as a guide. It’s also a great laid back plan if you’re traveling with friends or family!

One of my three planned destinations, the Haight.

My first mission, despite the great coffee at the Kensington, was a short, sturdy espresso. I knew the general direction I needed to go to fulfill both my trolley and caffeine desires, so went out the front doors of the Kensington and turned–downhill, which in this case was left. Walking just a couple of blocks I ran right into the beautiful Emporio Rulli at Union Square. It was a beautiful spot to enjoy the vibrancy of San Francisco at mid-morning. I ordered a delicious espresso and chocolate croissant and sat outside to enjoy them. Next it was time to ride the cable car!

My First Cable Car Ride

Cable cars are part of the really stellar San Francisco public transportation system. Everyone I encountered as I rode the cable cars and busses was extremely nice, patient, and helpful. They’re accustomed to tourists, so just remember to be nice to them and they will reciprocate. There are different ways you can buy tickets to use public transportation in San Francisco. I recommend just buying a Muni Pass online. It made it so easy to get around town without worry. Plus, it’s an easy app that looks cute on your phone. Cable cars require an extra ticket. You can find out all about Cable Cars at this really informative spot.

View from the back window of a SF Cable Car

You can actually look directly in front of you while having coffee at the Union Square Emporio Rulli and see where you’ll hop on a cable car. Be prepared to wait for a bit. I had a great time waiting in line talking to people I met from all over the world. None of us had a clue what we were doing or what to expect, which made it even more fun. When your car arrives, you’ll have the opportunity to get a seat inside (if there are any left) or hang onto the outside of the car! Hanging outside looked like fun, and I nearly went for it, but decided I’d better wait until a car came with available seats. Cable cars are a pretty wild ride!

Do I look smug about the seat I got?

I jumped on the Powell-Hyde line, snagged a seat in the back of the car where I could watch the view out the back window as we ascended those steep hills and passed landmarks like Lombard Street nicknamed “Crooked Street,” and enjoyed the view and everyone on board. It was a beautiful cloudy day. Watching the brakeman handle the car is amazing! I rode all the way to the end of the line at Ghirardelli Square and walked the short distance to Fisherman’s Wharf for lunch.

San francisco Bay Cruise

Lunch got put off for an hour, however, because there in front of me as I entered the Wharf was the Red and White San Francisco Bay Cruise fleet. Suddenly I realized a cruise around the bay was exactly the kind of easy, spontaneous, tourist activity I wanted to give me an overview of the city. As I climbed aboard and took my outdoor seat, the misty breeze blowing off the bay was wonderful. The jean jacket I’d packed definitely came in handy!

The hour-long cruises are equipped with headphones that provide a recorded guided tour as you pass under the Golden Gate Bridge, along the coast viewing historic San Francisco sites, and of course, by Alcatraz.

The View of Alcatraz from the deck of a Red and White Bay Cruise Ship.

I loved the panoramic views of the city from the deck of the boat!

San Francisco View from my Red and White Bay Cruise.

Back on land, it was definitely time for lunch.

Lunch at Boudin’s Bakery, Fisherman’s Wharf

I knew that the next day after my sister arrived, we would probably find an amazing seafood restaurant. Seafood is her favorite, and the next day we ate lunch at another San Francisco icon, McCormic and Kuleto’s overlooking the water. For my first day, though, I just wanted something simple, iconic, and fun that offered me easy vegetarian choices. I wandered right into the incredible flagship, Boudin Bakery at Fisherman’s Wharf. Boudin Bakery is a beautiful, amiable, windswept giant. As you walk by the windows outside you can watch the sourdough bread being created right before your eyes. They still use some of the “mother” recipe that is 150 years old! There were so many choices! I finally settled on the rustic tomato soup bowl, but there are so many others. And who knew that I could come home and buy those delicious breads for myself from Amazon! This is the San Francisco Sourdough Garlic Volcano Bread. Oh my.

After lunch I strolled through all the fascinating variety of Fisherman’s Wharf, Pier 39, and along the beautiful Embarcadero to the Ferry Building. It’s only about two miles from Fisherman’s Wharf to the Ferry Building, but you’ll want to take your time and enjoy all the rich variety –the shops, street performers, gardens, and view of the water. I took well over an hour, and had a wonderful time. The locals will tell you to keep alert. It is a crowded busy area. So remember to be mindful of your belongings. Near the Ferry Building, I looked up and saw Coit Tower. It turned out to be one of the highlights of my trip! From the Ferry building, you can take a tram, taxi, or walk to Coit Tower. I actually started walking, then I realized the challenge of Telegraph Hill, and opted for a quick taxi. I did walk down though as you’ll see!

Coit Tower and Telegraph Hill

Murals in Coit Tower

Coit Tower at 1 Telegraph Hill is a must-see, especially if you’re interested in art and history of the 1930s — or if you just want the city’s most panoramic views! Completed in 1933, Coit Tower is a 210 feet tall art deco structure built of reinforced concrete. Many people think it has the best 360 degree panoramic views of San Francisco, the Bay, and five counties! I loved the giant murals painted all around the interior circumference of the tower. Coit Tower was the pilot project of the New Deal’s Public Works of Art Project. Painted in the “social realism” style, the murals depict the variety of California labor in the thirties. You can read more about the history of this fascinating landmark, here.

If you want to buy a ticket (like I did), you can ride up in the period elevator and walk up the narrow flights of steps to the top of the tower to take in the views.

View of San Francisco from the top of Coit Tower

Telegraph Hill and the Haight

When I walked out the front door of Coit Tower and saw the iconic sign for Telegraph Hill and a path leading down, I thought, “What an adventure!” It was beautiful — and steep. Soon I came to a staircase that ran the entire length of the hill! As I kept going down, I encountered one of San Francisco’s most lovely neighborhoods with homes tucked into the side of the hill and stunning gardens.

Be ready though, those stairs are steep and there are 400 of them! Still I would not have wanted to miss this wonderful walking adventure. It was one of my most mindful times during my whole fun, spontaneous day. At the bottom of the hill I was ready to find a bus to my last destination before heading back to the Kensington for a rest. The Haight.


Here is another wonderful thing about the San Francisco Transit system. By this time my mind was still excited about my day, but the rest of me was getting pretty tired. I knew I was facing in the right direction, and pretty much just got on a bus and told the driver I wanted to go to the Haight. He told me where to get off to transfer, and the next bus driver did the same, and voila! I arrived at my destination. Thank you San Francisco drivers!


“The summer of love” may be a distant memory, but I still wanted to walk through the area and think about the history and images of that time. Now, Haight-Ashbury is a fun, cool shopping and restaurant area, with beautiful Victorian homes. I’d rested on my bus ride, so I walked through the streets enjoying the fun and funky shops. I stayed long enough to pick up some cool “vibes” before finding the bus back to Union Square and the Kensington Park Hotel to rest for a bit before I went out to the San Francisco Museum of Art and supper.

Art and Dining at San FRancisco MOMA

Entrance to the San Francisco Museum of Modern Art

Viewing and dining at San Francisco Museum of Modern Art was a perfect end to my day of solo travel in San Francisco. And best of all for me, it was just a ten or fifteen minute walk from the Kensington. As you can see from my photo, the featured exhibition was the work of the surrealist artist, Magritte. His work actually inspired some of my photographs from a quick run to Saint Louis. You can find out all about SF MOMA and its current exhibitions here.

Even the restrooms at SF MOMA are Modern Art!

Inside the ladies room at SFMOMA!

After a long delicious day of mindful wandering, watching the sun go down while dining at Cafe 5 in a rooftop sculpture garden at SF MOMA was a peaceful, satisfying end to my day. The menu is seasonal, so it’s always fresh and delicious. I had a wonderful hearty salad, but there are options for everyone, including a kids’ menu. Cafe 5 was the perfect choice for me after my long day, but there are other places to sample artistically-crafted fare at the museum, whether you just need a quick pick-me-up, or an elegant meal, you can whet your appetite here.

I loved my lovely long day of spontaneous mindful wandering in San Francisco. Do you have special San Francisco memories? I’d love to hear them!

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