Maddy Douglass

Knitter, lawyer, and safer beauty advocate in San Francisco. 

Loves coffee, crafting, and cheese plates.  


"Two redheads walk into a bar..."

...which happens to be on a boat! I know this sounds like the opener to a horribly crass joke, but really it's... the opener to a relaxing afternoon involving wine, cheese, and a lot of oceanic creatures!

Let me explain.

When Wanderable, the adorably hip honeymoon registry site that also offers activities for those who are pre-engagement (read: dating) or pre-pre-pre-engagement (read: single and hanging out with friends on the weekends), offers to send you on a San Francisco activity, you say yes.


And then when you peruse the options and see a Wine Therapy Tour on the Bay, you say "YES!"

Seeing as I am a (happily? willingly? decidedly?) single lady, I brought a dear friend along for the ride while exploring the best this wine cruise had to offer. We got all gussied up (She was even wearing wedges! What a classy date.), took a Lyft over to Pier 39, dodged tourists with toddlers in tow, and asked a nice security guard where Dock I was.

Well, first, I had to remember the word for "dock." And this was before the wine cruise, people.

Once we'd found the correct gate, we joined the other passengers who were clearly awaiting their maiden voyage on the Neptune.

Bobby the First Mate came to retrieve us, checked us off the list on his clipboard, and we were on our way to adventure!


One thing you need to know about Pier 39? It is covered in sea lions.

This is the place, actually, where tourists come from far and wide (like Topeka!) to view them in person. They are gigantic, slithering, slick from the water, shining in the sun, and undulating on the dock whilst constantly readjusting their positions and pushing each other back into the bay.

I probably could have just sat on a boat all day and watched these guys, but we had other sights to see.


Melissa, our cruise director for the day (conveniently married to Captain Kevin - it's a family affair), told us all about where she buys the wines from, how to put our wine glasses down properly while on the boat, and what kinds of cheeses were on offer for us that day, while the captain steered us skillfully out of the marina.


First, we went past the famous Pier 39 sea lions, as seen above. Then we carried on towards another small inlet on San Francisco's coastline, housing historical ships and military boats, and giving us a spectacular view of the city's skyline on this clear blue day.

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We saw more, and more, and more sea lions. I tell you, it's an invasion! One that I happily welcome. They are probably not as friendly as I imagine them to be, but from the safety of the Neptune, I was enthralled.

(Can you spot them below?)

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We went past Ghirardelli Square and turned left, heading out towards Alcatraz. Normally the tour goes up under the Golden Gate Bridge, they told us, allowing a different view of that iconic San Franciscan marvel - unfortunately, it was too choppy for us to go that far that day, so we stuck to tooling around the inside of the Bay.

(Maybe it's because I live in the area and drive over the bridge multiple times a month, but I didn't feel the detour took away from the itinerary at all. We still had lovely views of the city, as you'll see.)

As we neared Alcatraz, we got to witness an oil tanker being accompanied through the pass by the Coast Guard escort. I've never really thought about oil tankers needing an escort before, but it was nice to see everyone doing their job accordingly!



We noshed on the cheese and crackers with Melissa offering us tastings of a variety of wines (all from small, local wineries) whenever our cups got low and Bobby the First Mate volunteering to take as many snapshots of us as we desired.

Luckily, Rachel and I have perfected the art of photographing each other, so we got plenty of candid shots too without making Bobby be our indentured servant for the day. We wanted to spread the wealth amongst the rest of our tour, which consisted of a couple on their anniversary, an older man and woman, and a couple who seemed to be honeymooning.

It was a quiet, relaxed group - everyone was friendly, but there was no forced mingling, and everyone was free to enjoy the boat ride as they pleased.

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We began circling around Alcatraz (which I learned was only a federal prison from 1933 to 1963! Such a short career...) and it was slightly surreal to look at the abandoned structures and sheer cliffs and remember that not too many decades ago, people were actually imprisoned on The Rock.

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We made a full loop around the craggy island and headed south again towards the Bay Bridge and AT&T Park.

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(After getting a refill or two, of course!)


We ran into new friends along the way - this friendly chap encouraged us along while sunning himself pleasantly. And there was the sailor too!

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(That's a little seagull joke for you.)

Did I mention that we were being serenaded by the classics for the duration of the 90 minute cruise? Sinatra, Elvis, Sammy Davis Jr., Tony Bennett... all crooned and swooned as we gazed out the windows of the Neptune, transporting us back through time and space.

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Honestly, the highlight for me was when "Lights" by Journey came on at the exact moment we pulled into McCovey Cove. It could not have been a more perfect San Francisco memory.

When the lights go down in the city And the sun shines on the Bay Oh I want to be there in my city...

And just at the time when you think to yourself, "Alright, this is gorgeous, but I probably shouldn't drink any more wine this afternoon if I'm going to be productive," the boat makes a steady turn, you find yourself sailing past those now-familiar sea lions, and the Neptune has brought you back home again.



Thank you so much to Wanderable for sponsoring our lovely afternoon on the water, and thank you to Melissa, Kevin, and Bobby for showing us a fabulous time on the Neptune! Though this tour was provided free of charge, all opinions are my own. 

Brooks Brothers, bears, and bags - oh my!

High Five for Friday, vol. 10