5 things to do in the Castro district of San Francisco

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5 things to do in the Castro district of San Francisco

This month I am on reserve, which means I sit at home waiting all day for scheduling to call and assign me a trip. I never know what kind of trip I’m going to get, and to me, that is kind of exciting! Most of the time, if you are around me, you will hear me complain about reserve but it’s really not all that bad. I can get some of the best trips that way; trips that I normally don’t get to fly because of my seniority. This time I got a nice 18-hour layover in the heart of downtown San Francisco while Johnny is exploring Mexico City. I love San Fran, and here are my 5 things to do in the Castro District of San Francisco.

There are many reasons why I love visiting the golden coast of San Francisco, almost too many to name without going back and adding more and more to it. I remember the first time I visited San Francisco like it was just yesterday. To be honest, it was only 2 years ago, but hey, at my age I forget the timing of things easily. I know, I know, I am only like 30 but it sounds like a nice excuse. The first time I got to go to San Francisco was when hurricane Irma came to Miami. My roommates and I took off to one of their aunt’s house in the bay area.

So, back to the topic. Why mention only 5 things to do in the Castro District of San Francisco? Well, because I only had 18 hours there and I wanted to enjoy the day. A nice relaxing day at that. This means people watching, and basting in the sun. Even though today is cloudy and overcast. Normally on my layovers, I would go out and explore and walk a bunch, but I am a little congested and under the weather, so I knew all I wanted to do was relax.

1. Dolores Park Cafe

So here are the 5 things to do in the Castro District of San Francisco. First things first, buckle those belts… oh wait, this isn’t the safety video. The first thing to do is hop in an Uber and head over to Dolores Park Café. This Café is in a great spot. Right at the foot of Mission Dolores Park. A fellow flight attendant took me here last year sometime and it has been my go-to spot ever since. Not only is the food good, but it’s also just super convenient. This time I ordered the Pastrami on Rye. It was delicious, and oh so satisfying.

5 things to do in the Castro district of San Francisco
The Menu at Dolores Park Cafe is nice and fresh, and their fresh juice bar is nice too!

After you get your “picnic food’ from the café, stop by the Trader Joe’s close by for other snacks and a bottle of bubbly. I didn’t do it this time because I’m under the weather. Head up the sidewalk to enter Mission Dolores Park. Once you enter the park, I like to go sit near the top corner almost catty-corner to the café. It offers one of the best views of the city and the people.

2. Mission Dolores Park

I think the best part of Mission Dolores Park is the people watching. After you spread your blanket and get comfy, just look around. There are so many different types of people there to watch. You’ve got kids dressed all emo-like, in the hot sun wearing all black and long sleeves. Then you look the other way and you see some guy juggling and trying to show off to the ladies. Oh, and behind you, there are some boys learning to cheer or tumble as they build a human pyramid. Another reason why I love Mission Dolores Park is the vendors that walk around. I don’t know if they are licensed to sell stuff, but you can get a nice polaroid sometimes. Then there is the Rasta Man, who is my favorite vendor. He lugs around a cooler full of coconuts that he cracks open and pours in rum that mixes with the coconut water!

Needless to say, of the 5 things to do in the Castro District of San Francisco, people watching is at the top of the list. After you have been entertained, head on down towards the high school. But before you leave the park, use the bathroom right by the roller hockey court. Yes, I plan bathroom visits into my trips. Johnny always has to go to the bathroom so I’ve gotten used to finding the closest bathrooms. So, as you take a left and cross the train tracks, you enter the Castro District and all things rainbows!

One of the coolest things in this area to me is the history. I am a nerd, and this area of San Francisco has a lot of history. I am sure you have heard of Harvey Milk. If you haven’t, and you are gay then you need to read up. He lived here and campaigned here and got murdered here all because of him standing up to the “normal politics”. If you go to 545 Castro street, you will see the building where he campaigned and set up shop.

3. Moby Dick Bar

5 things to do in the Castro district of San Francisco

After you get into the gayborhood take a pitstop at Moby Dick Bar. It’s a fun little gay bar with a pool table and a couple of pinball machines. Another really cool thing they have is an aquarium above their bar. Super neat! Their happy hour includes corona + tequila shot for $6, or 2 for one frozen margarita’s. Overall the atmosphere is fun, and the bar staff is pretty cool. The same bartender has served me every time I have been. Well now that we talked about 2 of the 5 things to do in the Castro District of San Francisco, I need to go check on my first-class people. Oh yeah, did I mention I am writing from the jump seat?



They were good, just had to refill some coffees and feed a sleeper. So, let’s continue on!

After stopping into Moby dick’s there are a couple of options to move on to based on what you like. Here’s a great option! If you keep walking towards Castro Street you will come up on Midnight Sun. This is a nice bar, and they have wine ON TAP! In the early afternoon it’s nice and chill, but if you want a club like feel with almost naked men dancing on the bar definitely go at night. That’s Not really my thing but do as you please.

When you come out of Midnight Sun, you are pretty much on the main strip of the Castro District. When you get to Castro Street keep an eye out for the historic Castro Theatre. This is a great photo op. Not only do you get a nice vintage looking photo of the theatre but look down the hill and you will see rainbow flags galore. Also, a nice photo. When Dorothy went over the rainbow this is where the doll ended up!

If you like to shop, there are a lot of clothing and sex-like shops nearby. If you need some new sexy underwear then keep reading, because that is my next stop before our final stop of the evening.

Keep walking Castro Street to continue on our journey of the 5 things to do in the Castro District of San Francisco. Once you get to the top of the hill, you will see an intersection of cables for the cables cars that look like they would tangle up Spiderman. Cross the street and walk about 2 blocks or so past a gym and some restaurants.

4. Entour Boutique Clothing

When you get to another funky looking intersection, keep a weathered eye for a bar called the Lookout Bar. But don’t go in there just yet. See that cute little clothing store called Entour? Head on in and say hi, take a gander at the bathing suits and clothes and get yourself a souvenir. There are Lots of cute love-is-love shirts and even some nice button-up shirts. I got a cute bathing suit there, and it makes me feel sexy! I always stop in here to see what new sexy underwear they have.

5. Lookout Bar

After you shop around, come out and head on over to the Lookout. Normally there is a $2-$5 cover charge that supports a local LGBTQ organization. This time the cover charge supports a sports league. Head upstairs and if you’re lucky you can get a spot on the balcony overlooking the street cars and people rushing around. This is our final stop of the 5 things to do in the Castro District of San Francisco. I end my wonderfully relaxing layover with a nice cold draft beer watching people down below. (Oh yeah, it is kind of hard to figure out how to get on to the balcony, because when you are looking at the windows you don’t see an opening. Go to the corner and there is a sliding door.)

The view From the Lookout Bar.

Well, this concludes the 5 things I did in the Castro District of San Francisco when all I wanted was a peaceful relaxing day full of people watching and good drinks and cute little booty shorts. I hope you enjoyed, and let us know if you have done it, or better yet, What is your favorite spot(s) in the Castro?