The 10 Best Hillcrest Bars For A Fun Night Out

The buzzing neighborhood of Hillcrest is where you’ll find a huge collection of eclectic bars, cozy pubs, and plush cocktail lounges. It’s also a hub for San Diego’s LGBTQ+ community, which has led to Hillcrest’s gay bar scene being the liveliest in the city.

When Greg and I first met, we lived in Hillcrest and loved it. Hillcrest Bars are so much fun and have a relaxed and chill vibe. Want to dress up? Cool. Come in a T-shirt and jeans? Also cool. You instantly feel warm and welcomed whenever you walk into a bar in Hillcrest, and if you go more than twice, they will treat you like a longtime regular.

Start planning your next night out in this hip and happening district with our guide to the Hillcrest bars you have to check out.

Uptown Tavern

Cocktails and classic bar fare are what make Uptown Tavern a staple when it comes to Hillcrest Bars.

This University Avenue haunt boasts a gorgeous outdoor patio that is the place to be when happy hour rolls around or on Tuesdays when bottomless pasta is up for grabs for just $12.

While deciding between the chicken and waffles or the spicy wings, sample something from their endless selection of cocktails, which include spicy margaritas and fruity brambles.

Gossip Grill

Right next to Uptown Tavern is Gossip Grill. Widely regarded as one of the best gay bars in Hillcrest San Diego, Gossip Grill has a bit of everything, depending on what time of day you stop by, of course.

Mostly catering to women, Gossip Grill runs events all the time, from boozy brunches to drag shows, though you can also enjoy quieter nights around the firepit out back.

Not only have they nailed the perfect ambiance, but they’ve also created a fantastic menu with vegan and veggie options, plus quirky cocktails that go for as little as $12.

Alibi

If you’re after something a bit more laidback without being too quiet, Alibi on the corner of Richmond Street will fit the bill.

Matching the description of an old-school dive bar with ease, Alibi is a cash-only spot that’s kitted out with a pool table, jukebox, and healthy helpings of beer.

Don’t come hungry, as there’s no food served here, but what you will be treated to is famously heavy pours, reasonable prices, and hits from every decade.

Urban Mo’s

Urban Mo’s is an LGBTQ-inclusive bar that might just give Gossip Grill a run for its money.

Bingo, brunch, and diva nights will give you a flavor of what you’ll experience during a typical night at Urban Mo’s. Even when events are running, it’s well worth stopping for their $10 pitchers of drinks and their to-die-for brunch menu. As a heads-up, don’t overlook the PB&J French toast.

You’ll have the option of chilling on the terrace or busting a move on the dancefloor. Either way, it’s hard to have anything but a good time here.

insideOUT

Just a few steps further east is insideOUT, a swanky spot serving up premium seafood, juicy steaks, and $7 happy hour beverages.

I don’t think insideOUT has many competitors when the decor comes into question, as the water features, hanging flowers, and slick countertops speak for themselves.

They don’t offer the same range of events as many of its neighboring bars, as insideOUT focuses on craft cocktails, impeccable food, and a relaxed vibe, with the occasional shindig thrown in.

Number One Fifth Avenue

The best way to describe Number One Fifth Avenue is as a unique blend of a gay club and a dive bar.

As the name suggests, this long-standing institution is located on Fifth Avenue. Having established itself as one of the best bars in Hillcrest, Number One is famous for its diverse crowds, easygoing patio area, and late-night partying.

Drinks won’t set you back too much, but you’ll have the option to splash out on boujee cocktails for around $16.

Cigar Cave

Cigar Cave is right around the corner from Number One’s but has a totally distinct atmosphere.

Rather than dancing the night away, you’ll spend your evening listening to live music, smoking cigars, and sipping on craft beers or local wines.

The interior is a mish-mash of leather couches and beer barrels, with a huge variety of cigars on display and dimmed lighting that makes this place feel moody yet cozy.

Trust me when I say you don’t have to be a smoker to thoroughly enjoy a night at this little hideout, particularly if you’ve been seeking out somewhere low-key.

The Loft

Next, we’re moving slightly south down to The Loft, a busy gay bar that somehow manages to retain its understated vibe even when it’s crowded.

In addition to its drink selection, The Loft offers a wallet-friendly range of light bites, including $5 wraps and $10 mini charcuterie boxes for whenever you feel like a snack.

If you’re still not convinced, it’s worth noting that this was voted San Diego’s best gay bar not so long ago, meaning it definitely deserves its place on any list of must-visit Hillcrest bars.

Nunu’s Tavern

Another dive bar that welcomes everyone from all walks of life is the much-loved Nunu’s Tavern, a stone’s throw from The Loft.

Warm staff, retro furnishings, and build-your-own burgers abound, as well as cocktails that run from between $9-11. With prices like this, who needs happy hour?

In keeping with the yesteryear theme, be prepared for classic tunes and a dark interior, as well as generous servings of both food and drink.

The Merrow

We’re moving back onto University Avenue and heading to The Merrow, a go-to watering hole whether you feel like hitting the dancefloor or playing a game or two of pool.

This gay-friendly spot is where you’ll find regular live music sessions mixed in with insanely fun karaoke nights, cabaret shows, and a host of unique underground events that aren’t always easy to come by.

Happy hour usually runs between 12 and 8 p.m., which gives you pretty amazing bang for your buck, even in an area that’s famed for its relatively affordable drinks.

Regardless of what you like in a bar, I have little doubt that you’ll come across somewhere that tickles your fancy on this list. Because of Hillcrest’s walkable nature, you’ll easily be able to tick off more than one of these night spots during your visit.

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