Your sojourn begins at Lips (3036 ECB), San Diego’s monolithic stronghold of sassy drag and dining. You’ll want to make a reservation, because each showing at this glamtastic joint is packed with giddy bachelorettes and unwitting birthday boys. Servers with names like Cheyenne and Cassidy bring foofy cocktails called The Screaming Kiki or Spanky’s Pomitini while you browse a menu riddled with snort-worthy dishes along the lines of Cheesy Drag Balls, Disco Dollie’s Wild Mushroom Ravioli, and Better Than Your Mama’s Lasagna. Speaking of Mama, the food is nothing to write home about, but you aren’t here for the eats.
The provocative spectacle of Lips’ shows takes center stage, along with blushing soon-to-be-weds who invariably get dragged onstage to be simultaneously harassed and heralded by the glittered performers. All the cocktails hover around the $10 range and are very much whatever, but again, this is about the experience. They have a dress code clearly stated on their website, so don’t wear shorts and be aware that there is a $15 food minimum along with a $5 cover on weekdays and $10 on weekends.
3025 El Cajon Boulevard, San Diego
2850 El Cajon Boulevard #3, San Diego
Sated with sequins, you continue west to Tiger! Tiger! (3025 ECB), probably the least dively locale on the block. This bike-up bar specializes in top-of-the-line craft brews and quality wood-fired sandwiches. The menu — highlights: pork belly banh mi and kick-ass curry fries — speaks for itself, so you take added pleasure in the open-air back patio, where you can nibble and drink among hops and greenery trestled in the awning. Get down on $9.99 steins (one liter) until 6 p.m. daily. Down the block you run into the nascent Barn Brewery (2850 ECB), which, true to its name, brews farm-style saisons and makes a proper burger to go with it.
There is nothing dive about this destination, so you savor some tasty suds before moving on to Utah Street where, if you’re lucky and it happens to be the third Friday of the month (6 to 10 p.m. ), you’ll stop into the BLVD Market, San Diego’s premier pop-up street-food monthly. Nosh on anything from Maine lobster, vegan pizza, empanadas, and Ethiopian fare while you sip on a rotating cast of cocktails from the onsite bar, Calypso Club.
2306 El Cajon Boulevard, San Diego
By now you’re thirsting in earnest for a proper dive, so you head down to Gilly’s (2306 ECB). Here, you find sweet nectar. No theme whatsoever, just valiantly botched karaoke conquests, cutthroat billiards, cheap-ass beer, and sloppy barmates. Busch, that quintessential dive beer, rocks at $2.75 a pint. Even the higher-end beers go for a measly $3.75 a pop when showcased as the beer of the month. But the real joy here is steak dinners (6 p.m. every Tuesday until the meat runs dry), attentively charred by Samurai Steve, with sirloins starting at ten bucks (with baked potato and iceberg salad to boot) and shrimp skewers with sweet chili sauce for $4. If only to drive home the dive factor, the owner is “Big John” Haedrich, who is rumored to be a former pro wrestler who escaped from East Germany. The bar touts a solid 7 a.m. to 2 a.m. shift, but the back porch, the obvious destination of choice, is accessible from 9 a.m. to 9 p.m.
Red Fox Steakhouse
2200 El Cajon Boulevard, San Diego
Now that you’ve gotten your grime fix, you cross the street to Red Fox Steakhouse (2223 ECB), an ancient piano bar that one would readily call “dive” on, were it not so damn classy. The demographic here is primarily an older crowd peppered with local youngsters, who are just as eager to partake in the classic steakhouse menu while listening to piano and clarinet tunes emanating from the timeworn, wood-paneled corner. You get the sense that things haven’t changed at all here in a good half-century, and it puts you at ease. Cheap well cocktails come out exactly as an old-school cheap well cocktail should come out, which is to say, potent but not overbearing. The dim lighting makes every occasion feel like an illicit liaison, and it’s thrilling.
2223 El Cajon Boulevard, Lafayette Hotel, San Diego
Modern bar and restaurant Hope 46 in the attached Lafayette Hotel & Swim Club serves up some amazing American cuisine coupled with beers and cocktails, but it’s on the opposite end of the spectrum from anything that could reasonably be dubbed a dive (though happy hour sees drafts and wells at an honest $4 each), so you continue on to Pizzeria Luigi (2121 ECB), where you grab a thin-crust slice to soak up the sauce and most likely indulge in one of their many taps for $5 a pint or, if the spirits are moving, $15 a pitcher. As much an urban art gallery as it is a timeless tribute to East Coast pie, Luigi’s caters to a consistent stream of regulars and newcomers.
The final stop on your Dive Boulevard stumblefest is the most recognized “dive” in the area, Live Wire (2103 ECB). Sure, the jukebox spills a roll call of San Diego punk tunes, and the crowd is occasionally somewhat rough around the edges. But the bar highlights a cycle of choice brews, hulking cocktails, and most divey of all, tall cans of Pabst Blue Ribbon. This is the western end of the road for the mighty Boulevard, and the pink glow of her designating sign glows warm in the distance as revelers smoke cigarettes around Live Wire’s ever-collapsing metal bicycle sculpture. The bar opens at 5 p.m. and is home to some of the raddest bartenders in town, provided you are acquainted with even the most basic of tipping protocol. Take a look east and imagine: at one point, as old Highway 80, this very boulevard once connected clear to Savannah, Georgia.