Last week for Spring break, I surprised my fifteen-year-old daughter with a trip to Northern California. As Jordan enters the throes of adulthood, I feel her slowly slipping away. I know it’s normal, but I don’t have to like it. Until this year, her journey to school took her five doors down. Now the commute has her leaving and returning with my husband—in total darkness. We needed to reconnect. I also wanted to expose her to places and experiences California had to offer. Our journey began and ended in the complex city of San Francisco.

Parc 55, one of Hilton’s premier properties, is where we laid our heads the first two nights. The hotel sits in the Financial District, but teeters on the edge of the Tenderloin. If you’re not familiar with the Tenderloin, drive through. Streets are lined with both store-bought and make-shift tents and their occupants. Crowds huddle together on sidewalks sitting, laying, talking, and making transactions I try not to think about. Uncomfortable to see, yes, but not to be missed if you want the complete picture.

Thanks to Dylan’s Tours, we spent an entire day with a small group visiting all of San Fran’s well-known spots, including Chinatown, Twin Peaks, Haight Ashbury, The Mission District, and Pacific Heights. The tour left at 10:00 am so we had a little time to explore Fisherman’s Wharf. Rolando, our young, enthusiastic guide made the day a blast! The sun was shining and there was no sign of Karl, San Francisco’s famed fog. Rolando dropped us in a few spots for tourist pics, and in Sausalito, he left us for an hour so we could shop and grab a quick bite. Venice Italian Deli has the best avocado clubs! Muir Woods was last on our list. With only an hour, we hustled our way through the trails, past the crowds of Sunday-afternoon-smart-phone-photographers, and ended the day being dropped in Chinatown.

I used to think there were two kinds of travelers, those who took organized tours and those who were smarter, more adventurous, and preferred discovering all the less-traveled gems on their own. That might work if you have a ton of time to research and wander. And missing all the cool sites, the ones that make a city famous, is no fun. So who’s the real dummy? A tour on the first day is the absolute best way to get a taste of everything. You can always go back and explore favorites and new areas later. Whoever said, “with age comes wisdom” was pretty smart!

On our third day we left the city and headed north, but I’ll give you the scoop in my next post. While I’m thinking of it, if you plan to cross the Golden Gate Bridge, make sure to sign up for the toll program with your rental car company. There is no stopping to pay tolls. No one told me and now my $7.50 toll is $27.50.

On a Friday, after four glorious nights up north, we made our way back to San Fran, to another Hilton in the Financial District, where I put the car to rest in the painfully expensive hotel garage. If you can hold off renting a car until it’s time to leave the city, do it. The parking is expensive everywhere. $67 per night at the hotel, besides the public transportation is a decent way to get around. The street cars run frequently, about every ten minutes and are inexpensive at $2.50 for adults and $1.25 for kids. Tickets are good for ninety minutes. The cable car is pricier at $7.00, but good for a one-time experience. Be sure to sit on the outside.

Restaurants are sell-a-kidney pricey. The hotel recommended the historic John’s Grill on Ellis St. for cheap and delicious dinner. Our shared salmon entrée and salad was $50. We also had a decent dinner at Franciscan’s Crab Restaurant at the Wharf that cost about the same for a single soup and appetizer. The best inexpensive food we found was at the Ferry Building. The empanadas at El Porteno were $6.00 and to die for. Steamed Chinese buns at The Imperial Tea Court were $3.00 and also quite tasty.

We accidentally ended up at Pier 39, a mecca of flashing neon and overpriced chain places. We escaped as quickly as possible. On our walk back we passed a couple of naked bicyclists with the words Donald Trump tattooed on their rump cheeks. Moving right along…

Angel Island is California’s version of Ellis in NYC and was the first stop for Asian immigrants. It’s a beautiful place to escape the city for a day, or overnight if camping is your thing. Jordan and I took the ferry over to spend the day hiking and were lucky enough to be there for their annual Spring festival and adult Easter egg hunt. We won two free trolley tours and some warm baked cookies from the only café on the island. Lunch at the café was tasty and reasonable. After our hour-long trolley tour around the island, we took the Sunset trail and hiked our way to the summit before rushing back down so we wouldn’t miss the last ferry.

On Easter Sunday, our last day, we wandered the city, made our way up ridiculously steep hills to a street festival and parade in the beautiful, residential Cow Hollow/Russian Hill area. Afterwards, we visited the famous Lombard street and watched as cars of all sizes lined up and navigated their way down the hairpin turns.

On the red-eye back to Orlando, I contemplated our days in San Francisco. Yes, the city is a perplexing mess of both beauty and hideousness with dwellings ranging from $2.00 tarps to forty million dollar mansions. Many say it is a place where the dredges of society—the lost, the broken, the forgotten end up. But like everywhere we travel, there’s immense beauty and lessons to be learned here.

So view it as you wish—a failing fusion of degenerates and millionaires, or a multifaceted city, buck-naked and out on a limb, stepping away from conventionalism, and trying to make a difference.