I have been visiting San Diego for 30 years now. It started out as a fun, gay-friendly destination for my group of friends when I lived in Chicago and has now become my second home. As the fun guncle of the family, I get to enjoy both of my sisters with their families have moved here and created full lives. Lucky to have this opportunity to stay with family as Airbnbs and hotels will be your biggest expense while visiting this sun-drenched mecca.
My favorite place to work remotely is OB Beans Coffee Roasters on Newport. They serve a strong cup of drip coffee in an airy, open space. As a remote worker, I justify the $5 price tag for a drip coffee, which has become standard these days, with my 4-hour workday as I take up real estate writing this newsletter. Make sure to get a nap in before or after jumping on your bike because the hills can be killer if you aren’t used to them. I thought, well, I bike almost every day in my Bed-Stuy neighborhood in Brooklyn, grabbing a Citi Bike for errands and rarely having to take the train. But those hills, after filling up on booze and food, can be a challenge, yet they also rev up your appetite for the next place on your list.
After a beautiful afternoon sail in La Playa Cove Anchorage, we jumped on our bikes and headed for "Golden Hour" between 4-5pm at Ponyboy Bar & Restaurant in The Pearl Hotel. Half off all appetizers, $9 cheeseburgers and $1 oysters. We got the Pickle Dip and Cornbread & Butter, and of course, the oysters. We chased down these tasty bites with a surprisingly complex $10 glass of Chardonnay.
I can’t talk about San Diego without mentioning a couple of fun dive bars. Just down the street from Ponyboy is Good Bar. Walking in, we were greeted by women in crop tops and cut-off jean shorts, giving Hooters vibes. It does nothing for me, but as in most places, we were greeted with a friendly smile and quick service. Not being a beer drinker myself, I still feel that when in Rome, do as the Romans do. So I put down a couple while enjoying a very talented Motley Crue cover band. I think the alcohol buzz is the only thing that got my legs moving in order to bike up Nimitz Blvd to our next stop at Catalina Lounge. Legs a little wobbly but I made it, and as I looked around, the Wisconsin boy in me felt right at home. Cozied into large, curved, leather-bound burgundy booths, we finished our adventure with one more drink and then I headed back to my sisters' for a dead sleep from exhaustion and a full, happy belly.
With the world cup watching parties around the city, the next day, I jumped back on the cruiser bike to meet another long-time friend to watch the soccer game at Belmont Park. The viewing area set up to see the game was at capacity, so we biked our way up the boardwalk to Mo’s for "Social Hour" from 4-6pm. Another Wisco-feeling dinner club.
Bar at Mo’s
Blue cheese-stuffed martinis, crazy delicious Wagyu beef sliders, bacon jam meatballs, and iceberg wedge are the standouts. Make sure to saddle up to the bar in the high-back leather chairs and chat up the other locals to get some tips. After all the food, drinks, and weed, we ended our evening with a wobbly walk down Bird Rock Waterfront. It's a gorgeous spot during the day or night.
Evening view from Bird Rock Waterfront
Whistle Stop Bar Sketch Party
New location added to the Drink and Draw World Map. Every week a new locations are added as I find them. Great resource when traveling solo through the world.
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