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PubClub Travel Adventures: From Alcatraz To Irish Coffee, Our Three Days In San Francisco

August 4, 2026 by kevinwilkerson 2 Comments

A Press Trip Turns Into Rooftop Wine, Cable Cars, Alcatraz, Fisherman’s Wharf and Plenty of Unexpected Laughs

Ashley & Kev's Travel Adventures San Francisco
Ashley and Kev enjoy their complimentary Napa wine on the deck of the Hilton Union Square in San Francisco. Photo: PubClub.com

San Francisco has iconic landmarks, legendary bars and neighborhoods unlike anywhere else in America. During three days in the City by the Bay, we packed in as much as possible—and somehow still found time for rooftop wine, Irish Coffee and a few memorable travel mishaps.

By Kevin Wilkerson, Editor of PubClub.com

Part of the PubClub Travel Adventures series, following firsthand journeys to nightlife destinations and unforgettable experiences around the world.

The e-mail came and I responded with the quickness of a Stephen Curry three-pointer.

It was an invitation for a three-day press tour with the San Francisco Union Square Hilton. Ashley and Kev’s Travel Adventures were headed to the City by the Bay!

Ashley had been to San Francisco but had never really experienced San Francisco. “One time was with a boyfriend at the time and we did it on the cheap,” she said. “Very cheap.”

So I was anxious to show her parts of “the City,” as locals call it, not all of which was on our travel bloggers’ itinerary.

One thing about San Fransisco is that it contains more landmarks than pretty much any other city in the world. It has the Golden Gate Bridge, Lombard Street, cable cars, the famous ship’s wheel sign at Fisherman’s Wharf and Alcatraz Island. If landmarks were a criteria for making great cities, San Francisco would win the title of “Best City In The World” in a landslide.

And, by the time we were boarded the plane back home to Los Angeles, Ashley and Kev had seen and done all of these things, as well as a few others, added like the frothy topping on the Irish Coffee at the Buena Vista.

We did have our series of usual comical travel misadventures, but those did not impede us. Rather, they made us laugh.

Ashley & Kev's Travel Adventures San Francisco
Ashley shows off her excitement and the travel bloggers’ gift basket at the San Francisco Union Square Hilton. Photo: PubClub.com

The adventure began shortly after we entered our room. We received a knock on the door and a hotel staffer came in with a tray full of goodies, including a bottle of Napa Valley wine. Ashley shrieked with joy and surprise (this was her first press trip) while I was excited that we would get to have some good wine on that large balcony overlooking San Francisco Bay.

But, of course, an entire city lay 36 floors below our feet, and not being ones to sit back and  wander “what if,” we headed out onto the streets before we were due to meet up with our fellow travel writers.

It was a mid-Friday afternoon and we were seeking a drink and a snack before dinner (which was to be at the outstanding Urban Tavern in the Hilton). I wanted a “San Francisco bar,” which I define as an old, narrow place with lots of wood. Due to Ashley’s inquiring of a doorman at a place that did not serve food, we wound up at a spot down an alley named Louie’s.

Ashley & Kev's Travel Adventures San Francisco
Louie’s was our first stop in San Francisco and it set the tone for a fun weekend. Photo: PubClub.com

What a cool bar! It was buzzing with activity, which we attributed to the incredible drink specials posted on the wall. I had a Hamm’s beer and a shot for 6 bucks, Ashley had a beer and a shot for $7 and we shared incredible tacos – they had both a soft shell and a hard shell – for $12.

Score! Our trip was off to a great start.

Dinner was exceptional and we probably should have called it a night a drink earlier at the Hilton’s excellent rooftop lounge, Citiscape, because we were scheduled to go to Alcatraz in the morning. But with good drinks and sensational nighttime views of the city in a comfortable setting, there are times when you think about tomorrow, well, tomorrow.

Ashley & Kev's Travel Adventures San Francisco
Hanging out on Alcatraz. Photo: PubClub.com

The Alcatraz Cruises tour experience was great – Ashley later said it was her highlight of the trip – and with it being just past Noon when we returned to the City, we had time to explore some San Francisco landmarks.

We walked from the Alcatraz landing at Pier 33 to Pier 39 and paused for selfies at the Pier 39 ship’s wheel Fisherman’s Wharf sign.

We strolled along the chowder-in-the-sourdough-bread-bowl outdoor seafood counters that’s another symbol of San Francisco (and was featured in the James Bond film View to a Kill), into the hilarious Crazy Shirts t-shirt shop (slogan on one shirt: “Will Trade Husband For Wine) and over to the Buena Vista.

Ashley & Kev's Travel Adventures San Francisco Fisherman's Wharf
We made it to another San Francisco landmark, the “ship’s wheel” sign at Fisherman’s Wharf. Photo: PubClub.com
Ashley & Kev's Travel Adventures San Francisco Buena Vista Irish Coffee bar
Ashley walks into the Buena Vista, San Francisco’s famous Irish Coffee bar.
Ashley & Kev's Travel Adventures San Francisco Buena Vista Irish Coffee bar
Another San Francisco landmark: the Buena Vista and its famous Irish Coffee. Photo: PubClub.com

This one-time saloon is famous because it created the Irish Coffee drink, and bartenders make them on the equivalent of an assembly line. Ashley was able to make one of the veteran slingers laugh and even crack jokes in the middle of his mixing madness: “What you think they just hired me for – my good looks!?”

From there, we quickly abandoned our plan to ride a cable car up to Lombard Street when it was obvious the line at the Hyde Street turnaround would not have us back at the hotel until probably the next day, so we walked up that huge hill.

Ashley & Kev's Travel Adventures San Francisco Lombard Street
Naturally, we had to go to Lombard Street, San Francisco’s crooked street. Photo: PubClub.com

Ashley loved Lombard Street, more so for its gorgeous flowers than for its crooked quirkiness.

We did get our cable car ride (tho, due to an error on my part, not for long enough), had dinner at the highly-popular Kin Khao Thai restaurant in the Hilton’s Parc 55 hotel, enjoyed a concert by SF Jazz and, the next day, rode over the the Golden Gate Bridge on our way to the wine country on a tour from Tower Tours in the Hilton.

Ashley & Kev's Travel Adventures San Francisco Golden Gate Bridge
We cross the Golden Gate Bridge on the way to the wine country. Photo: PubClub.com

We then went back to Citiscape where – after a few more drinks – we “kidnapped” a few visiting British journalists with rum drinks at the Smuggler’s Cove tiki bar.

San Francisco offers a lot to the traveler but it also delivers a lot, and Ashley and Kev’s travel adventures experienced quite a bit of best in the City by the Bay.

Ashley & Kev's Travel Adventures San Francisco Smuggler's Cove tiki bar
We go out in style – our last adventure in San Francisco was at the Smugger’s Cove tiki bar. Photo: PubClub.com
Smuggler's Cove tiki bar San Francisco PubClubette Ashley
The final drinks of the weekend were with this fun crew of journalists from England at the Smuggler’s Cove tiki bar Photo: PubClub.com

Now Hop On The San Francisco Party Bus To…

• San Francisco Travel Misadventures: A Travel Blog

• San Francisco City Guide

• San Francisco Neighborhood Guide

• PubClub Taste Test: The Cable Car Cocktail

• Bay to Breakers

• San Francisco: The One Line Single People Need To Know

Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and nightlife for more than two decades. While working as a newspaper reporter, he received an Associated Press award for investigative journalism.

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Filed Under: San Francisco Tagged With: Ashley & Kev's Travel Adventures in San Francisco, Irish Coffee, PubClub Travel Adventures, Three Days In San Francisco, travel bloggers

Reader Interactions

Comments

  1. kevinwilkerson says

    June 6, 2019 at 9:00 am

    Thanks MVP! Definitely will keep ’em coming.

  2. Mike VonPlinsky says

    June 6, 2019 at 5:09 am

    Great trip overview … could use it as an itenary!! Keep ’em comming!

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