Travel Thursday: The Ultimate Guide to an Unexpected San Francisco

The continental United States is full of endless backdrops that beg for exploration. While it may take a lifetime to discover the deserts, forests, and beaches around the nation, it is the list of the largest metropolitan cities that you have to get through as soon as you can.

San Francisco, the biggest and baddest city on the West Coast, is a must-experience destination that has been one of the key players in California history. From its majestic Golden Gate and Bay bridges, to the richness found in Chinatown and around its diverse neighborhoods, San Francisco is the city that will make you feel like you are in a different place with each corner you turn.


All that aside, for gay travel, SF is one of the gay capitals of the world and if you haven’t already visited—what are you waiting for?! You won’t just find rainbow flags and good times in the city’s Castro district—you will be welcomed by friendly faces and inclusivity everywhere you go. It’s as if the whole city is pulsating “We’re here, we’re queer!”

It’s the place I go to when I’m sick of Southern California and want to feel like I am not in California. I know that sounds weird, but that’s totally the feeling SF gives you. The bay area, and Northern California in general, comes with different sensibilities. So if you go there, know you aren’t in typical California—and don’t you dare call it ‘San Fran’ or ‘Frisco’—they’ll make you into clam chowder!


I recently got back from a weekend trip to San Francisco, which is only about a one hour plane ride away for me (or a 6-7 hour car ride give or take potty breaks and Instagramable pit stops). Having been to SF before, this trip to ‘The City’ was to discover the unexpected elements that make San Francisco truly unique.

We arrived on a midday Alaska Airlines flight. Just when we had gotten comfy in our seats–we were there! We didn’t even get to finish our inflight movie! One of the nice things about flying from Southern California rather than enduring the hours of traffic up the 5 Freeway.

When I travel, I almost never rest so it was a jam packed trip for me and my boys as soon as we landed at the SFO airport.


Here’s a list of what you may want to explore to get a taste for the unexpected San Francisco:


Arguably the most colorful neighborhood in San Francisco is the Castro. From afar you can see a larger-than-life rainbow flag welcome visitors as if saying “Yasss Queens!” as it waves. Everyday, the Castro’s queer identity is a tourist attraction. The beauty found in the Castro is in the subtleties. While the entire city of San Francisco is on the progressive spectrum, the Castro feels like a world of its own, inviting members of the LGBTQ community and their allies to experience a slice of life.


While I venture out to the Castro each time I’m in San Francisco, it is impossible to write up this travel piece without mentioning the importance of this neighborhood in the LGBTQ history of our nation. Take yourself to the Castro and visit places like Twin Peaks Tavern, the historic Castro Theatre, Harvey Milk Plaza, The Café, and Dolores Park to absorb the energy of the Castro.


EXPERIENCE Tenderloin Neighborhood

Considered to be the toughest neighborhood in San Francisco—and maybe the US—the Tenderloin is a culturally diverse and rich downtown neighborhood that makes up approximately 50 blocks. The neighborhood dates back as far as the gold rush period of San Francisco and served as one of the premiere hotspots for nightlife early in SF’s development. The term ‘tenderloin’ comes from various theories: a fine or fancy cut of meat—the ‘soft underbelly’ of vice—or the wedge shape that the neighborhood makes up.


Many travelers to San Francisco are afraid to venture out into the Tenderloin because most of its streets are inhabited by transients. Behind all of this, is a part of the city that has a lot to offer, if you just go past the surface while you admire the vibrant murals that tell the narratives of the people who have left a mark on the Tenderloin.

In the Tenderloin exists a non-profit Community Benefit District (CBD) that is dedicated to improving the quality of life in this neighborhood. 

According to the TLCBD website:

The Tenderloin District is home to many residencies, small businesses, hotels, schools, nonprofits, parks, theaters, restaurants, United Nations Plaza and much more. The Tenderloin has continuously been a vanguard of social change and deserves to be recognized as such. It is a neighborhood whose history is as uniquely diverse as its people.


On a walking tour of the Tenderloin, I encountered some incredible urban spaces that make the already colorful neighborhood truly shine:

826 Valencia – dedicated to supporting students ages 6-18 with their writing skills and helping teachers get their students excited about writing.

Fleet Wood – A gallery and boutique that features locally made art, clothing, home goods and more!

Tenderloin Museum – A full space that celebrates the Tenderloin neighborhood and sheds a light on the most misunderstood neighborhood in San Francisco. Currently, the Tenderloin Museum is producing a play about the 1966 Compton’s Cafeteria Riot which was the first recorded militant uprising by the queer community against police in US history. The play will run from February 22-March 17, 2018 at the New Village Café.


Onsen – A Japanese inspired bath and restaurant that serves up new American cuisine and sake tastings in the front and a luxurious, relaxing sanctuary of a bath in the back. You would never expect to find this place nestled deep in the Tenderloin, but if you do, take the time to enjoy the spa or any variety of their services. The restaurant is adorned with 1,000 paper cranes that were hand folded by the owners!


Hallway leading to spa at ‘Onsen’

Esan – a modern twist on authentic Thai cuisine that took years of preparation between Chefs Tom Silagorn and Chanon Hutasingh. The chic urban restaurant feels upscale, but serves a down-to-earth experience with modern touches.


There was so much to experience on this tour of the Tenderloin, but you will have to discover it in greater detail!

STAYHilton San Francisco Union Square

I am one to use Airbnb or Misterb&b, if not—I try to find an affordable hotel that really immerses me into the travel destination. This time around, the Hilton San Francisco Union Square was the best option for many reasons. It’s in a great location, central to everything! It has great food right in the hotel! And the VIEWS from our room and from the hotel’s Cityscape are one of a kind!


Cityscape – If you’re looking for the most picture perfect sights of the city, look no further than Citscape at the Hilton! It’s the only 360 degree view of San Francisco and their drink selection is one of the best! My favorite was their spicy paloma. When you visit Cityscape you’ll order a drink, but get drunk off the views!


Urban Tavern – One the first floor of the Hilton you will find Urban Tavern which is definitely not your typical hotel restaurant. This metropolitan gastro pub has a full bar with over 50 wines and local brews to go with their diverse menu which includes Pork Belly & WaffleCharred Spanish Octopus , 8-hour Bolognese, and Roasted Jidori “Peking” Chicken—are you drooling yet?! And when you’re too drunk and full to walk, your room is just an elevator ride away!


Assortment of apps from ‘Urban Tavern’
Octopus at ‘Urban Tavern’

The Hilton also has Poached, a daily breakfast buffet—or should I say “FEAST”? where you will find an international selection for breakfast or brunch. Whether you’re an early riser like me or you want to sleep in and cuddle with your pillow a little longer, Poached will fill your belly and warm your heart with its made-to-order omelets, dim sum, yogurt bar, salad bar, griddle selections and more! I guess that’s why I gain so much weight during travel.


EXPERIENCEAunt Charlie’s Lounge

If you’re looking for an authentic San Francisco night out with the gays, look no further than Aunt Charlie’s Lounge. No need to head to the Castro to visit Aunt Charlie—this legendary hole-in-the-wall is located in the Tenderloin—which I’ve already told you lots about! On the weekends, Aunt Charlie’s features the Hot Boxxx Girls, a drag show that celebrates life and fills up the tiny dive bar. Locals and out-of-towners alike flock to Aunt Charlie’s to experience the drag sensations that are these hard working ladies. When I learned that Aunt Charlie’s is dubbed ‘the oldest drag bar in San Francisco’ we had to check it out. The oldest because it is still standing and because the drag queens are also still standing. One of them said they were 71, Yaaaaaasss Grandma! Werk!


We didn’t have a reservation, but were lucky enough to grab some seats at the bar right in front of their iconic neon sign. So make a reservation if you want a confirmed place to sit! If not, you’ll be stuck in the back with the rest of the bar flies, but a nice night nonetheless. At the end of the night, the queens are nice enough to let you take photos with them, but be a good guest and tip the ladies—let’s keep historic places like Aunt Charlie’s alive for gay-nerations to come!

With the queens at ‘Aunt Charlie’s’



Whether you’ve visited San Francisco before or have never been, SFMOMA is a MUST-SEE/DO stop on any trip to the bay area. After a three-year closure, SFMOMA is back with an expansion that offers 7 floors of gallery space in a 10-story new building designed by Snøhetta.



Here you will find everything from photography to painting to sculpture and performance art. Upon our visit to the SFMOMA we discovered some Frida Kahlo, Andy Warhol, Walker Evans, and giant spiders by Louise Bourgeois! You can run through the exhibits quickly if you are strapped for time, but believe me, you will need at least half a day to be able to peruse the exhibit spaces. Oh, and pictures are okay as long as there is no flash! Get your Instagram and Snapchat ready!




Located right by Union Square at Parc 55, this Thai restaurant will disarm you from the moment you walk in. Kin Khao, which translates to ‘eat rice’, has 1 Michelin star and has been regarded for its simple aesthetic, but flavors that pack a punch! This place is great for groups or one-on-one dinners. We tried an array of appetizers which they call ‘Bites’:

Nam Tok Beans (V)Iacopi Farm cranberry beans tossed Isaan-style with lime, chili, rice powder, light soy, shallots, scallions, mint, cilantro


Yum Som-O (V) – Winter Citrus, cucumbers, peanuts, herbs, toasted coconut, shallots, puya chili, white soy+lime vinaigrette

Mushroom Hor Mok Terrine (GF) – Curry mousse in-a-jar with mushrooms, crisp rice cakes


Khao Kan Jin (GF) – Pim’s favorite street food from Chiang Mai. Banana leaf-wrapped steamed pork+rice+blood sausage, served with garlic chips, fried shallots, raw shallots, cilantro, lime

Everything was mouth-watering and overflowing with flavor. But my favorite item at Kin Khao was their Pretty Hot Wings (GF) – Nam Pla fish sauce+garlic marinade, tamarind+Sriracha glaze

Quite possibly the best wings I have EVER had! You have to try these—but if you don’t eat spicy, beware!! You can’t miss Kin Khao on your next trip to SF!

EXPERIENCE – Alcatraz Cruises “Behind-the-Scenes”

If you’re anything of a history buff or a sucker for places with great backstories, you have to explore Alcatraz. Nevermind that Alcatraz is one of the key tourist locations for San Francisco, Alcatraz is a token of California history that is full of mysteries being unlocked every single day. An island off the San Francisco mainland, also known as ‘The Rock’, Alcatraz was once a world-famous federal penitentiary that held prisoners from around the U.S. who had a knack for escaping or were high risk. The prison was active from 1934-1963, being home to some of the most notorious prisoners including the legendary Al Capone. Prior to being a prison, Alcatraz was the site for the first American lighthouse on the West Coast and was a huge harbor defense fort during the Civil War—even though no one ever invaded!

Today, the island is a registered National Park that welcomes over 1.7 million visitors per year!



If you have never been to Alcatraz, or even if you have, I recommend you exploring the ‘behind-the-scenes’ areas of Alcatraz as this is a new attraction on The Rock and will give you some interesting perspective that is definitely unexpected. The tour begins with the Alcatraz Cruise which departs from Pier 33 at specific times (check your reservations!)

BE AWARE: this tour lasts approximately 4.5 hours, ventures into tight and dark spaces, and sells weeks (or months) in advance.

On this ‘Behind-the-Scenes’ tour we went deeper into the prison’s history and were taken into what is known as the ‘Citadel’ which served as a solitary confinement cells where prisoners stayed for weeks in darkness and with little food. The space below is limited and we entered a few at a time with hard hats, but the energy in the Citadel was strong as we got up close and personal with markings and messages prisoners left behind—all without touching anything of course! Shout out to Ranger Wendy for a great tour!


One of the hottest places to be in San Francisco is PIER 39 at Fisherman’s Wharf. This destination for tourists is what I would consider a one-stop shop for entertainment! I have visited PIER 39 before, but never had learned so much as I did this trip.

With 100+ restaurantsshops and attractions, plus special events, live daily entertainment and more, you’ll never need something to do, but figuring out exactly what to do with your time at PIER 39 may take a while.

Sea Lions – A favorite of many visitors to PIER 39 are the sea lions that arrived to the area in January 1990. What started as a group of 10-50 sea lions has now turned into upwards of 900 sea lions which attract millions every year. They are adorable and will make you jealous of their leisurely lives! You will find the sea lions year-around at PIER 39’s K-Dock.



Fog Harbor Fish House – PIER 39 has a vast number of places to chow down while you are enjoying your day, but Fog Harbor Fish House is a spot I had never tried and definitely didn’t expect. Fog Harbor is a family owned and operated restaurant that will give you the quintessential San Francisco waterfront experience. The restaurant’s dining room looks out upon the San Francisco Bay and Golden Gate Bridge while you enjoy their huge menu of 100% sustainable seafood.

This place is awesome! It was packed on a Saturday night, but with reason—the food is incredible! There was some things on the menu that I wasn’t prepared for—but when I tried them I died, came back for another taste, then died again—at the end of the story I survived, but took the leftovers back to my hotel.

When you get there, you have to order the following:

Blue Cheese Garlic BreadFresh sourdough, topped with garlic, Pt. Reyes blue cheese and herbs

Red Chili Garlic Shrimp (GF) – Red chili paste, onions, peppers and garlic

Crispy CalamariFried jalapenos and onions, served with lemon aioli

Crab CakesTwo crab cakes, citrus beurre blanc, mango relish

Lobster Mac & CheeseDo I even have to describe this one?!

Yes, I tried all of that and let me tell you, you haven’t had garlic bread until you’ve had blue cheese garlic bread!

I couldn’t eat anymore, but if I could, I would have definitely tried their clam chowder, which San Francisco is known for. It must be good if all this other stuff was delicious!

Oh, and I had the Perfect Hibiscus MargaritaEl Charro Reposado, Patron Citronge, hibiscus syrup, fresh lime and agave served up and topped with Patron Citronge foam

Okay, maybe I had two of those—some would say tipsy, I would say happy.

I was surprised to learn so much more about PIER 39 as well. They have some great attractions coming up like The Plunge a new ride that will drop strapped in riders from dozens of feet in the air, but not before giving them a 360 degree aerial view of PIER 39 and beyond! Also coming up is new The Flyer opening later this year that will take riders on a journey through San Francisco using a giant movie screen.

TASTE/EXPERIENCEHornblower Brunch Cruise

An incredible end to our trip to San Francisco was the Hornblower Brunch Cruise. Who doesn’t love brunch?! Now add cruising around the San Francisco Bay and passing the Golden Gate Bridge and Alcatraz and where have you been all my life Hornblower?! The Hornblower Brunch Cruise is the best way to tour the bay, take the best photos, and get drunk off your ass with bottomless champagne and a buffet that will make you loosen the button on your pants. On the morning of our cruise it was chilly, so check the forecast and dress appropriately. Although, it’s San Francisco and you should always layer, just in case.

The buffet had a huge variety of salads and breakfast items and a full dessert section with waffles, cakes, fruit and I’m done. A pianist plays throughout the entire cruise and throws out interesting facts about San Francisco as you enjoy some good times with the ones you’re with. Throughout the two-hour cruise you are free to wander about the ship and go up to the second and third decks to be one with the waves and the seagulls.

The Hornblower Brunch Cruise is perfect for special occasions like birthdays, anniversaries, bachelor/ette parties, etc. The sweetest part about our cruise is when we were about to dock, the pianist played “I Left My Heart in San Francisco” and couples from all walks of life stepped onto the dance floor and punctuated the beautiful afternoon with love.

For more information on the adventures that await in San Francisco, visit or check them out on Facebook or Twitter! #sftravel

Until next time, San Francisco!

1 thought on “Travel Thursday: The Ultimate Guide to an Unexpected San Francisco”

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