Friday: Explore Downtown San Diego

Check into The Guild Hotel.

Make this new downtown San Diego boutique hotel your home base for the weekend. The Guild Hotel opened this year in a stunning, 1924 building that once housed the Army Navy YMCA. Its minimalist, modern design features nods to the most fashionable eras of the building's past: the '20s and '60s. Rooms are bright and light-filled with sharp, clean lines throughout, high ceilings, and in the Artisan King rooms, floor-length, velvet drapes that can be pulled over large cathedral windows. You'll find only a single art piece and a few furnishings in each—like a tufted leather headboard and mid-century modern light fixtures—but here, less is truly more. Make time for a cocktail at The Guild Bar, a glamorous, Art Deco, and totally 'gram-able lounge adjacent to the lobby. // The Guild Hotel, 500 W. Broadway (San Diego), theguildhotel.com

Have happy hour at Pure Project.

San Diego has roughly 200 craft breweries, but Pure Project is hands down one of the city's most talked about (especially among industry pros). This past summer, they opened a second location uptown in Bankers Hill, right on the edge of Balboa Park. Despite the industrial, urban setting, Pure Project pays homage to its Costa Rican roots with so much greenery you might as well be chilling in the jungle, and their beer names are on theme too—see Rain, an unfiltered pilsner or Tropical Mist, a misty citrus blonde. // 2865 5th Avenue (San Diego), purebrewing.org

Dine at Barbusa.

It's not a proper trip to San Diego without dinner in Little Italy, and while it's hard to go wrong in this neighborhood, Barbusa always hits the mark. Owned by San Diego's legendary Busalacchi family—Joe Basalacchi is credited with essentially pioneering Little Italy here—Barbusa is a modern reinvention of their many, many traditional Italian concepts from over the years, contrived by Joe's sons, PJ and Joey. The restaurant serves classic Sicilian cuisine with a crudo bar, handmade pasta, and pizza. Inside it's always electric, even on Monday nights, and by the end of the meal, you'll be calling your server family and inviting them to Thanksgiving. Make a reservation if you want to eat before 9pm. // 1917 India St. (San Diego), barbusa.com

Have a nightcap in the Gaslamp.

The famed Gaslamp Quarter is at the center of San Diego nightlife; Sign of the Whale, on the lower level in a former 1800s jailhouse, is its newest hot spot for a late night dance party. Sip one of their inventive, ocean-themed cocktails like Pier Pressure (Hendrick's Orbium, lemon, pea blossom), or if you're in a group, split a giant Sangria Tsunami. Hangover: likely. // 672 Fifth Avenue (San Diego), signofthewhaleca.com

Saturday: San Diego has an equal dose of nature and culture.

Start the day at Herb & Eatery.

Head back to Little Italy in the morning for coffee and breakfast at Herb & Eatery. This brick warehouse-esque space has been transformed into a stunning and incredibly cozy neighborhood cafe by celebrity chef Brian Malarkey; sister restaurant Herb & Wood lives in the back. Order up your go-to morning coffee or an energizing smoothie—the Drop the Beet, for instance, is made with roasted beets, blueberries, green apple, coconut water, and orange juice. The breakfast menu is oh-so Californian with a few fun twists. Yes, there's avocado toast, but also a Thai croissant (chicken Thai sausage, fried over easy egg, gruyere, arugula, and spicy aioli) and the Egg McPuffin (housemade English muffin, fried over easy egg, white cheddar, yuzu aioli, and your choice of sausage, bacon, or avocado). // 2210 Kettner Blvd. (San Diego), herbandeatery.com

Hit the beach or take a hike.

San Diego beaches are the embodiment of SoCal living. With 70 miles of coastline, there are literally dozens of options, so you can choose your own adventure. Mission Beach and PB (Pacific Beach), which are adjacent to each other, are popular, classic beach towns favored by the 20-something crowd, with plenty of nearby bars, taco stands, a boardwalk, and amusement park. OB (Ocean Beach) is also often busy, but has more of a laid-back, surfers vibe where the streets are lined with live-in vans. Some of the most pristine beaches can be found in the upscale, seaside towns of Coronado and La Jolla.

If beach bumming isn't your thing and you like to be more active, head north of La Jolla to the Torrey Pines State Natural Preserve. Protector of the rarest pine tree species in the U.S., the 1,700-acre preserve of gorgeous coastal wilderness has eight miles of hiking trails. Choose the Beach Trail for a double whammy of adventure and sand.

Grab an early dinner at Parc Bistro and Brasserie.

Get your seafood fix at this charming yet casual French bistro in Bankers Hill, starting with escargots or a seafood tower to share. Lobster enthusiasts can have their pick between lobster mac and cheese, lobster risotto, or lobster arancini, but if you prefer land animals, you won't be disappointed with Parc's steak frites or the 18-hour braised short rib bourguignon. Pair your meal with a bottle from the Sommelier Selection of their wine list if you're up for splurging. // 2760 Fifth Avenue (San Diego), parcbb.com

Catch a show.

The Old Globe Theatre in Balboa Park isn't just a cool replica of Shakespeare's historic Globe Theatre in London (which eerily even has its own history with fire), but it also often serves as a hatchery for many hit Broadway and Tony award-winning productions, like A Gentleman's Guide to Love and Murder and Dirty Rotten Scoundrels. Catch the likes of The Winter's Tale (Oct. 30 through Nov. 17, 2019) and Tony Award–winner August Wilson's Jitney (Jan. 18 through Feb. 23, 2020). // 1363 Old Globe Way (San Diego),theoldglobe.org

Sunday: Brunch, Shopping, and One Last Beer in San Diego

Brunch at Kairoa Brewing Co.

Head over to University Heights for brunch at Kairoa Brewing Co. and request a seat on their massive roof deck. Fun fact: This quiet, up-and-coming neighborhood was formerly an ostrich farm. The New Zealand–themed brewpub opened in early 2019 and specializes in Kiwi-inspired dishes like fish-and-chips, a Kiwi burger with beet and egg, and of course, lots of lamb—lamb fries, lamb meatballs, and even lamb tacos. The menu also has a slew of vegetarian, vegan, and gluten-free choices. As for the beer, they work with New Zealand hops as much as they can. Try the Cheeky Buggah or the Sneaky Buggah, their signature Belgians. // 4601 Park Blvd. (San Diego), kairoa.com

Peruse Liberty Station.

Before taking flight back to NorCal, wander around Point Loma's Liberty Station, located just a mile from the airport. The site of the former Naval Training Center, which dates back to 1932, the historic buildings are now filled with boutiques, restaurants, chic coffee shops (Moniker General is a coffee shop and retail space in one), and an arts district. You can take home something custom from a local artisan. The anchor of Liberty Station is the Liberty Public Market, which is a lot like the SF Ferry Building or Napa's Oxbow Public Market. // Liberty Station Public Market, 2820Historic Decatur Rd(San Diego), libertystation.com

One last hurrah at Eppig Brewing.