“Milanese Apertivo" at Monello
1250 Prospect Street, Suite B10, San Diego
Sequestered below street level on Prospect, this seafood enclave has a broad assortment of mezcal, some of which find its way into tasty signature cocktails like the Oaxacan Old Fashioned — smoky mezcal, tequila, agave nectar, and mole bitters — offered for $3 less than usual during Happy Hour (4-7pm and 9pm to close every day) offered along with incredible tuna tostadas, avocado tacos, and serrano ham croquettes (all under $7). Throw in the fact they’re doing their darndest to up their beer game and the future of early-evening imbibing looks bright, indeed.
1801 Morena Boulevard, San Diego
The High Dive
Daily specials like Wednesday’s assortment of $6 pizzas or the delicious protein-netted web of bacon-studded blue cheese adorning a plate of crisp french fries is enough to get me to this comforting Bay Park hub, but I love the fact that local beers — of which there is a vast assortment from outstanding operations like AleSmith, Ballast Point, and Coronado Brewing Company — are two bucks less (3-6pm, Monday-Friday) than the rest of the board. Plus, from a super-friendly front of the house to the al fresco patio at the back of the house, the place is built to be easygoing and low pressure, just what Happy Hour is all about.
9675 Scranton Road, San Diego
Karl Strauss Brewery
For half a decade, every one of my and my colleagues’ promotions, new job offers, or other vocational accomplishments was celebrated at this brewery-owned eatery’s outdoor patio, looking out upon a gorgeous Japanese garden and waterscape. But it was the quality beer, including cask-conditioned “firkin” offerings rolled out every Thursday at 6pm, and discounted-yet-decadent Happy Hour appetizers including fried calamari with chili aioli, spice-dusted fries, and a massive nacho stack (3-6pm, Monday-Friday) that made Uncle Karl’s business ’hood respite a welcoming after-work hang. (Note: closed for remodeling until Easter.)
4292 Esplanade Court, San Diego
La Jolla Strip Club
The only “strip club” I hit with any regularity (or at all, for that matter), this one’s a bit under the radar. (And for those not familiar with its play-on-words handle, it’s one of those places where you grill up your own steak. Get it?). The fact it’s buried in a part of town saturated with slightly more affordable dining options and across the street from a mall (a distance few shoppers are willing to traverse unless they see the word SALE), makes it easier to grab a pool table and enjoy a few rounds of eight-ball along with $4 draft beers. Eats like sliders, lobster mac ’n’ cheese, and my personal vice — nachos — are ripe for the taking at $7 (3-7pm, Monday-Friday, and 5-7pm Saturdays).
750 W. Fir Street #102-B, San Diego
“Milanese Apertivo" at Monello
This Little Italy haunt invites guests to “drink like an Italian.” So, what does that mean? In Monello’s case, the purchase of a drink or cocktail (including several made using exceptional house-made sweet vermouth from noted mix-mistress Jen Queen) acts as a passport to complementary small-plate offerings from chef Fabrizio during what he refers to as “Milanese Apertivo” (4-7pm, daily). Those edibles vary by day, but expect takes on traditional Italian street food like cheese- and meat-stuffed piadine and fried cauliflower, the likes of which owners Valentina DiPietro and Guido Nistri love so much that they opened this venue to celebrate them.
560 Fifth Avenue, San Diego
The gargantuan burgers and perfectly crispy yet tender fries at this Italian mobster-themed Gaslamp spot are as delicious as they are filling, which keeps me coming back regularly, especially during Padres season. (Most years, it’s one of the few bright spots of the 162-game bummer.) Half-priced appetizers and $4 pints (including modest, but quality craft offerings) during Happy Hour (3-6pm Monday-Friday, and 9am-12pm Saturday-Sunday) up the appeal, game day or otherwise. Bonus: On Mondays, Friars fans can toast victory or drown their sorrows at bargain rates during reverse Happy Hour (9pm to close).
8980 Villa La Jolla Drive, San Diego
I spent much of my mid-20s shooting pool with my buds and sharing pitchers of this brewpub’s Ragtop Red Ale and extremely affordable appetizers. That was way before the space was taken over by accomplished brewer Marty Mendiola, who has earned high-profile awards for his beers over the past half-decade. The pool tables are still there, the beer is even better, and the Happy Hour pricing (4-7pm, Monday-Friday) has remained well within my budget, making it both easy and rewarding for me to take a trip back in time while indulging in modern upgrades.
10450 Friars Road, San Diego
San Diego Brewing Company
This place remains one of my favorite local traditions. Many are the Wednesdays when my drinking buddies and I would show up early at this 20-year Grantville mainstay for Happy Hour (4-6pm, Monday-Friday) and bide our time, shooting the breeze over $3 house beers like Grantville Gold and Old Town Nut Brown Ale, while waiting for the stroke of seven when the kitchen raised the drumsticks on meaty 50-cent wings. There’s a different brewer manning the tanks, and ownership recently remodeled, opening the place up and spreading out seating. But the same discounts, wings, and happy energy remain to keep me returning.
4505 La Jolla Village Drive Suite C-1, San Diego
When I hit wine-centric spots, I’m looking for variety. Man cannot live on a singular house chardonnay. This wine-and-health focused chain gets it, and its Flights and Flatbread deal provides it. It’s available daily, and though it’s not actually a Happy Hour deal, it falls in line with one, and you should know about it. Fifteen bucks (or $20 for premium wines coming in at over 90 points) yields a shareable plank of thin, nicely topped lavash crust, tasters of three different vinos, plus a full pour of one’s favorite of the trio, or as I call it, a complete evening.