"It seemed like a matter of minutes when we began rolling in the foothills before Oakland and suddenly reached a height and saw stretched out of us the fabulous white city of San Francisco on her eleven mystic hills with the blue Pacific and its advancing wall of potato-patch fog beyond, and smoke and goldenness in the late afternoon of time." — Jack Kerouac, On the Road

San Francisco is a place that has captured writers, artists, and musicians. It is my favorite city I have ever been to in the United States. I created an itinerary in advance based on others’ advice I found online. My mom and I made the trip of lifetime in 2015 over Memorial Day weekend.

Day 1

Our plane touched down early afternoonish to a quiet calm San Francisco Airport. After we collected our luggage, we followed the smooth transition navigating to the AirTrain blue line to the rental car center. There is only one other person in front of us in line but it feels like an eternity until we get our car. The black 4 cylinder Toyota is the first car I have ever rented in my life. Used to driving a Mustang, I have to push the peddle down to the floor and we are off. Navigating on an old Iphone, my connection is slow, so I just head west excited to check in our hotel. As we enter from the highway to the city I am lost in the hills and streets as my phone is too slow to load the route. Suddenly we reach the top of a hill and come down to one of the craziest streets in the world. Without intention, we are coming down Lombard Street surrounded by hoards of people taking selfies and policemen directing traffic. I crank the wheel as hard as I can back and forth as we make our way to the bottom. I apologize repeatedly to my mom who is turning white. Finally we make it to our hotel located near Fisherman’s Wharf.

We check in and head out to walk around Fisherman's Wharf, one of the most touristy spots in San Francisco but something you can’t miss. We ordered crab sandwiches, take in the street performers, and people watch. Passing many vendors, we make our way to Pier 39. Pier 39 has plenty of shopping and food, but the best attraction is the sea lions. Barking, playing, and catching sun, sea lions are the center of attention. Male sea lions can weigh up to 850 lbs and fight over the best spot to lay out. Too full for dinner we end the evening with dessert at Ghirardelli white chocolate sundaes looking at a sunset and the Golden Gate Bridge.

Day 2

Sleeping in, I grab a coffee in the lobby and we head down to Hyde Street to purchase trolley tickets. This is a must do when you are in San Francisco. We wait patiently in line and hop on. The trolley climbs up and down the hilly roads. We reach our stop on a side street near Chinatown. I could spend hours walking up and down the streets of Chinatown. It's like traveling across the world. Make sure you venture off the main stretch so you can see things like the large fish tanks on the side streets.

Not far from the Beat Museum, we head over to check it out. The Beats were the hippies before the 60s. The 1950s generation of free spirits, writers, and poets. San Francisco was a popular gathering place at the time and many stories capture the spirit of the city. I pick up a copy of Jack Kerouac's Dharma Bums. I romanticized in my mind what this city must have looked like then. Today, modern San Francisco, is one of the most expensive cities in the United States to live. The high cost of housing is one of the primary reasons. Many have to commute from outside the area or have lots of roommates. We continue back to explore more of Chinatown and get some cheap souvenirs.

We catch a taxi to Hyatt and Ashbury streets. These streets with large, colorful Victorian houses were once home to band members of Jefferson Airplane, Janis Joplin, Grateful Dead and lots of other hippies in the 1960s. Boutique shops and trendy restaurants are what remains. We get lunch and explore the shops. If you are looking for a cool tie dye shirt, I highly recommend this street.

Dinner is my favorite fast food: In-N-Out Burger. Life does not get much better than this for me.

Day 3

It was Memorial Day. We get up relatively early, for vacation and for us, around 7 am. The chauffeur gets the car, and we are off to Muir Woods. It is my first time traveling across the Golden Gate Bridge. After seeing photos of it all my life, it is incredibly surreal as we cross over the bay. We were fortunate we left early and are one of the first vehicles at the park. Muir Woods is home to the California Redwoods. My head and neck are cranked up as we take in the view of these massive trees. Taking a large deep breath I feel my lungs fill with fresh air. Since we are the first ones on the path, we spot mule deer and other animals. The pathway and trails are accessible in areas, so even if you have someone who needs a wheelchair or stroller, I recommend it. The gift shop has a restaurant and it’s packed. My mom and I join an Australian couple who has been traveling within Canada and the United States for the past two months. We head out, and stop at a few beaches in the area. I feel refreshed. On the way back to the hotel we stop at several vista points and take in the Golden Gate Bridge.

For dinner we head down to Boudin at the Wharf. Boudin Bakery is famous for sourdough bread. We order the world famous bread bowl with clam chowder. It is more than amazing and is another must do if visiting San Francisco.

Day 4

I love wine. We are not going to San Francisco without a visit to Napa Valley. Our concierge at the hotel was really helpful and recommending different wineries for a day trip. It is overwhelming when looking at how many there are. Before we head to the wineries, we cross the Golden Gate bridge once again and stop for brunch in Sausalito. This was probably my mom's favorite place and somewhere I could see us staying the next time we came to California.

Our first winery stop is Viansa Sonoma. Surprisingly this was actually our favorite stop of the whole trip, and my mom ended up ordering a few bottles. The rolling hills and grounds around the winery and vineyards are a perfect place to relax and have a conversation. Continuing to Napa Valley, I was in awe of the number of vineyards. We ended up going to Sterling Winery. Sterling Winery is up the side of a large hill. My mom has a fear of heights, but maybe she had the liquid courage from the previous stop. She had no problem getting in the Aerial Tram. This winery had good wine, but some of the people seemed pretentious. My favorite line from my mom was when she asked how the wine would pair with Cheetos. We also had to wait way too long for a cheese platter. While we were waiting Steller Jays, which look a lot like Blue Jays, ate people’s food. It was an amazing experience, and I need to go back to see more.

We stop at a candy store and I purchase way too much. The evening is spent getting a sugar buzz and watching the Golden State Warriors.

Day 5

I really had to push my mom to go on the Alcatraz Tour. What could be so exciting about an old prison on a rock? We waited in a long wrapped line by the pier and loaded the boat. On the ride out you realize it’s much further away than it looks. At least it did to me. Upon arrival you receive headphones that you can pause, control and start the audio tour. I was so impressed with the stories and hearing different perspective from the guards and prisoners. One of the things that surprised me the most was hearing how the guards’ children at one point attended a small school on the island. You really get the feel and perspective as you walk through the cells of what it was like. I can only imagine how hard it would be seeing the lights and sounds of San Francisco, while being a prisoner on this island. My mom really enjoyed the tour too.

After coming back to shore, we walked for lunch in Little Italy. We really treated ourselves this time at Tony's Pizza Napoletana. Somehow between the drinks, really good pizza, and dessert we lost track of time. By the time we left it was already late afternoon. Our mother son trip of a lifetime had come to an end.

San Francisco is a city that has something for everyone, and I know I will return again.