17 San Diego Staycations Ideas for Families this Summer

September is San Diego’s unofficial second summer—the crowds thin, the weather stays warm, and the city’s calendar somehow gets even busier. This month brings stadium-sized rock shows, Broadway’s buzziest comedy, a new anime convention, world-premiere theater, gallery openings, food festivals, and the first signs of spooky season. Whether you’re ready to lean into fall or determined to keep summer going, here are the best things to do in San Diego this September.

Concerts & Festivals | Theater & Art Exhibits | More Fun Things to Do

Concerts & Festivals in San Diego This Month

9/2 

As Guns N’ Roses storm into decade five, their appetite for destruction persists. During their Snapdragon Stadium concert, hear the hard rock anthems, new material and a set from The Black Crowes.

9/23

Kehlani is proof that the romance and earnest sensuality of old-school R&B will never go out of style. Hear her take it back to the aughts at Viejas Arena.

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Theater & Art Exhibits in San Diego This Month

9/6-10/11

From the silver screen to The Old Globe stage, John Carney will Begin Again (again) with a world premiere musical adaptation featuring new songs—courtesy of Train—and a story overflowing with hope. 

9/12-10/17 

The concept of work is a guiding principle for San Diego native and multidisciplinary creative noé olivas. Observe his community-informed approach via Tierra y Cielo (Earth and Sky) at Best Practice Gallery. 

9/18-10/25 

Two workers grapple with the weight of their roles at a temporary migrant shelter in Mario Vega’s world premiere play Our Lady of the San Diego Convention Center, set for citywide performances. 

9/26-2/28/2027

Luminous visions of peace and the Punjabi-American roots of Rupinder Kaloti inform The Gathering, a wondrous unification of family foretold via paintings at Oceanside Museum of Art. 

9/29-10/4 

It’s Mary Todd Lincoln’s world and we’re just living in it. See the presidential paramour barrel to her way to stardom at the Civic Theatre during Oh, Mary!, Cole Escola’s political spoof. 

More Fun Things to Do in San Diego This Month

9/5 & 9/6

Pros and Con(vention)s: Anime San Diego will debut at the San Diego Convention Center with cosplayers, panels and more than 400 vendors well-versed in Japanese animation.

9/11-10/31 

Scaredy cats beware: SeaWorld San Diego’s Howl-O-Scream embraces frights forged in darkness. Enjoy an ominous lineup of live shows, scare zones and bloody bars ahead of Halloween. 

9/12

The best parts of Artivál and the Alley Cat Art Walk have united for the free Alley Cat Art Fest, an all-day outing for live music and immersive artwork in Downtown El Cajon.

9/12 & 9/13 

Take a Grecian vacation for a fraction of the price during the annual Cardiff Greek Festival, two days of immersive cuisine and culture—with plenty of dancing—on the Encinitas coast.

9/13-9/20

Step away from the stove! The California Restaurant Association has eight days of eating experiences with your name on it. During San Diego Restaurant Week, explore by meal, neighborhood or cuisine for your personal dining plan. 

9/16 

Nourish yourself with an all-inclusive spread of Pacific Beach eats and locally-crafted artwork during the HeArt of PB Restaurant Walk on Garnet Avenue.

9/19 

When it comes to stand-up comedy, Chelsea Handler is always ready to roast. See Handler tell anecdotes and skewer an assemblage of victims during her Balboa Theatre performance. 

Play is underrated. Somewhere along the way, someone decided it was something we should outgrow. That you A good song comes on, and they dance. A game appears, and they’re in. Someone hands them a melting ice cream cone, and somehow it’s the best part of the day.

Adults tend to need a reason. Or maybe just the right setting.

That’s part of what makes the Del Mar Wine & Food Festival feel different. Yes, the week revolves around food and wine, with celebrated chefs, winemakers, and restaurants drawing crowds from across the region. But what lingers afterward is the conversations that stretch a little longer than expected, the strangers who become dinner companions, the live music that pulls people out of their seats, and the rare chance to spend a few hours simply enjoying yourself without much of an agenda.

The Grand Tasting is the festival’s centerpiece, bringing thousands of guests together over two days for hundreds of bites and pours. But some of the week’s most memorable experiences happen on a smaller scale. In the days leading up to the main event, intimate dinners, chef collaborations, and guided tastings create opportunities for guests to interact more closely with the people behind the food and wine and with each other.

Here’s your guide to the 2026 Del Mar Wine & Food Festival happening September 30–October 4.

Wednesday, September 30

Signature San Diego Opening Night Party at Monarch Ocean Pub

Start festival week the San Diego way: ocean views, Baja-inspired bites, and a drink in hand as the sun goes down. The Signature San Diego Opening Night Party at Monarch Ocean Pub sets the tone for the week ahead with a walk-around tasting experience celebrating the flavors that make this city impossible to replicate. It’s an evening of fresh coastal cuisine, bold Mexican flavors, Baja seafood, and plenty of local favorites—all served against one of Del Mar’s most iconic backdrops. Consider it your first official toast to the weekend ahead…

• Monarch Ocean Pub | 1555 Camino Del Mar, Del Mar
• 5–9 p.m.
• Get Tickets 

Friday, October 2

Celebrity Pickleball Tournament Presented by Justin Vineyards & Winery

Wine and competition make an unexpectedly perfect pair. You can join Drew Brees and celebrity players at Barnes Tennis Center for a pickleball tournament benefiting Feeding San Diego, where the sidelines are just as exciting as the court. Grab a paddle, cheer from the sidelines, or simply enjoy a glass of wine while the action unfolds. The day blends friendly competition with an all-inclusive tasting experience.

Since year one, Del Mar Wine & Food Festival has partnered with Feeding San Diego to raise $100,000 in support of the organization’s mission to fight hunger across the region. Every serve, sip, and bite helps give back to the community that makes this festival possible.

Remember that pickleball paddle you swore you’d use? Time to put it to work.

• Barnes Tennis Center | 4490 W Point Loma Blvd, San Diego, CA 92107
• 11 a.m.—3 p.m.
• Get Tickets

Thursday, October 1

Rioja Uncorked at Rancho Valencia

This is essentially a passport to Spain with no airport required. Set among the lush grounds of Rancho Valencia, Rioja Uncorked celebrates one of Spain’s most iconic wine regions with an evening of exceptional pours and thoughtfully paired bites. Guests will sip their way through Rioja wines while enjoying a menu featuring everything from Hiramasa crudo and uni toast to duck rillette, birria mini tacos, Cardiff Crack tri-tip sandwiches, and a sweet finale from Karen Krasne of Extraordinary Desserts (date night plans, solved).

• Rancho Valencia | 5921 Valencia Cir, Rancho Santa Fe
• 6–9 p.m.
• Get Tickets

Friday, October 2

Justin Wine Dinner with Chefs Kaitlyn Weber, Buddha Lo & Jackson Kalb

Justin Wine Dinner sounds simple: three chefs, one unforgettable table. But chefs Kaitlyn Weber (Estancia La Jolla), Buddha Lo (Top Chef), and Jackson Kalb (Top Chef) are taking you on a one-night-only culinary ride where three styles collide over a multi-course menu paired with exceptional pours from Justin Vineyards & Winery. Set in Estancia’s coastal estate, the evening unfolds course by course with pairings from Justin wines as each chef brings their own style to a menu focused on craft, connection, and a bit of friendly culinary overlap. It’s the kind of culinary conversation that only happens when very, very talented people cook together. 

• Estancia – Olive Lawn | 9700 N Torrey Pines Road, La Jolla, California 
• 6–9:30 p.m
• Get Tickets

Saturday, October 3

Official After Party at Guesthouse La Valle

August is San Diego at full volume. Summer crowds are still chasing sunshine, but the calendar belongs to locals who know this is when the city really shows off. One night you’re dancing under the stars, the next you’re watching thoroughbreds with a plate of oysters in hand, catching Broadway hits, wandering gallery exhibitions, or rallying on a downtown pickleball court. Whether you’re looking for live music, festivals, theater, food, or an excuse to spend as little time indoors as possible, these are the August events worth putting on your calendar.

JUMP TO: Concerts & Festivals | Theater & Art Exhibits | More Fun Things to Do

Concerts & Festivals in San Diego This Month

August 9

On the heels of Cross Pollination II’s release, house musician Lane 8 will co-headline FNGRS CRSSD x Cross Pollination, a day of back-to-back grooves at Waterfront Park.

August 11–16

Cross coasts at the Civic Theatre for a jukebox musical rooted in family, coming of age, and blossoming talent in Alicia Keys’ Hell’s Kitchen, inspired by the 16-Grammy Award-winning singer’s NYC upbringing.

August 23

Jeff Goldblum is a classic man. In his show at The Rady Shell, Goldblum will accentuate his old-school charm with his Mildred Snitzer Orchestra and the San Diego Symphony Orchestra.

Theater & Art Exhibits in San Diego This Month

August 1–October 10

Explore gallery walls lined with artwork juried by acclaimed artist Paul Mpagi Sepuya and chosen by the Athenaeum Music & Arts Library for its esteemed 34th Annual Juried Exhibition.

August 7

As you already know, we adore San Diego. That’s why we’re assembling the city’s crème de la crème—including over 90 curated vendors—in Liberty Station for our annual Best of San Diego Party, presented by Pechanga Resort & Casino.

August 12

Helado Negro and Reyna Tropical each specialize in bilingual music, songs overflowing with proud markers of Latinx identity. Hear the ear-tingling transmissions from their collaborative LP at Epstein Family Amphitheater.

August 16

Country music superstars, proud Georgians, and close pals Jason Aldean and Luke Bryan are doubling down on their summertime stadium tour with a boot-stomping concert at Petco Park.

August 27–September 6

The one-woman play Eleanor—told via the eloquent perspective of Eleanor Roosevelt—will make a limited return to the North Coast Repertory Theatre.

More Fun Things to Do in San Diego This Month

Now Through September 3

For six straight Thursdays, downtown’s Fifth Avenue will shut down and become the city’s first-ever street-style pickleball event. Bring a paddle and enjoy DJs, a wellness market, and zero-proof drinks at Gaslamp Urban Pickleball.

August 8

Del Mar Thoroughbred Club’s newest foodie event, the buttery Turf & Surf Festival, offers a luxurious combo of land and sea, built for watching trackside with a loaded plate in hand.

August 22

For the first time since 2019, the free Chula Vista HarborFest will hit the shores of Bayside Park with a classic car expo, lucha libre showdowns, and the chance to meet a mermaid.

August 29

Celebrate the seven decades (and counting) spent upholding Point Loma’s coastal landmark during Cabrillo Under the Stars, a 21-plus fundraiser with bites, Beatles covers, and, best of all, twinkling lights.

If you’ve ever wondered what it would feel like to perform on one of San Diego’s most iconic stages, here’s your shot. The Old Globe is looking for local singers, songwriters, and musicians to take the spotlight before performances of its upcoming musical Begin Again—and the gig comes with a chance to perform on the theater’s main stage and at a new community music event, Begin Again: San Diego Sessions.

Inspired by the opening scene of Begin Again, which makes its pre-Broadway premiere at The Old Globe this fall, the open mic–style performances celebrate local talent while giving audiences a taste of San Diego’s music scene before the curtain rises.

Solo artists and duets ages 18 and older can submit video entries here through Friday, July 10. Selected performers will be notified by July 14.

The public is also invited to Begin Again: San Diego Sessions, a free event on Monday, July 20, at 7 p.m. in the Globe’s Copley Plaza. Attendees can catch performances from top contest participants while enjoying discounted drinks from the theater’s pub.

“Begin Again is a story about hope and someone finding their light,” says Adena Varner, Director of Arts Engagement at The Old Globe. “The opening moment, which is what we’re excited about with this contest, is about an artist who’s unknown taking a chance at an open mic night—and then their life changes.”

“What I love about San Diego is it’s a space where hopes and dreams seem to actually be able to come true, and people get to find themselves, find their light and their voice, so I think the spirit of the show really resonates with who we are as San Diegans,” she says.

For director Lorin Latarro, the pre-show performances are a chance to weave San Diego into the production. While the musical has been developed in New York with New York–based musicians and actors, these performances create a direct connection between the show and the city’s local music community.

“One of the things Lorin is passionate about is wanting these performances to feel like San Diego, so we want them to be diverse,” Varner says. “We want these moments to look like us and all that that means… We have submissions from artists based in Tijuana, North County, and East County, so it’s geographically diverse, ethnically diverse, and we’re looking at age diversity as well.”

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The Old Globe has hosted community engagement opportunities tied to past productions—including an art contest and walk-on performances—but nothing quite like this.

“We’ve also never had an open mic night on the plaza, so we’re excited, and we really want the music community to know that they’ve got a place at The Old Globe, too,” Varner says. “We’re getting in the practice of making sure our community feels connected to our shows and have an opportunity to contribute in a way that’s meaningful and impactful for them.”

Begin Again is based on the 2013 film starring Keira Knightley and Mark Ruffalo, with a book by Jenna Clark Embrey and Molly Beach Murphy and music and lyrics by Pat Monahan of Train. Performances run September 6 through October 11, with opening night on September 17.

At the time of publication, The Old Globe had received nearly 100 video submissions.

Growing up in Carlsbad, I never quite understood why people vacationed there. What, so you want to check out the field where I have soccer practice? Pay my orthodontist a visit? Carlsbad just felt like a town by the beach, no better or worse than any other in the country. It took going to college out of state for me to actually understand just how rare a place like Carlsbad is.

Thanksgiving break my freshman year, my first time coming home after three months in the Midwest, my shoulders dropped. I rolled down the windows and drove to lifeguard tower 37—the hangout magnet for Carlsbad’s youths (and, in the summer, tourists)—and the smells of the ocean woke me right up like smelling salts do. I finally got it.

Carlsbad isn’t just a stopover town on your way to something better. It is the destination. Travel + Leisure named Carlsbad one of the top 50 places around the world to travel in 2026. From the whole globe, the travel magazine picked my home. Sure, we’ve got the Flower Fields and Legoland—but now it’s the smaller ships and indier dreams that are giving it street-level character.

It’s not just Carlsbad, either. People have talked about the “North County bubble” for decades—a force field that prevents its residents from traveling south of the 56. It’s often used derogatorily, and it’s a fairly accurate burn.

For decades, living up in North County meant giving up on culture, or at least culture within close proximity. But now, the main expansion of San Diego culture is happening up north. Central San Diego restaurants have started taking notice and are expanding into the area—spurred no doubt by Oceanside’s food boom and the Jeune et Jolie–Campfire–Wildland–Lilo constellation in Carlsbad. City Heights burger joint Key & Cleaver opened a new spot in Oceanside; the owners of Parc Bistro-Brasserie in Bankers Hill opened Parc Lounge in Rancho Santa Fe. Possibly the strongest market indicator is that Sam Fox—one of the most successful restaurateurs west of the Rockies—has started focusing on North County for his concepts. In 2025, he opened both The Henry in Carlsbad and Culinary Dropout in Del Mar.

For the ultimate insider guide, we found a handful of inspiring people who live and create and truly know six North County neighborhoods—San Marcos, Escondido, Oceanside, Leucadia, Rancho Santa Fe, and Vista—and asked them how they’d spend a dream day out and about in their town.

San Marcos

San Marcos is in full renaissance mode. The biggest story is that the grand North City vision is starting to peek through the scaffolding. It’s essentially the North County Downtown that’s been written in the tea leaves and discussed whenever someone gets stuck in traffic at the 5/805 merge: a 200-acre, pedestrian-friendly, mixed-use face-changer that’s slated for 2,600 homes, 350,000 square feet of retail and restaurants, 250 hotel rooms, and about a million square feet of offices and labs. Its most recent manifestation is 222 North City—a 12-story residential tower with over 450 residences, rooftop garden, pool cabanas, art installations, and almost 20,000 square feet of ground-floor retail (Necessity Coffee, Buona Forchetta, Draft Republic, Milonga Empanadas, and a grocery store anchor on its way).

Which means Restaurant Row is no longer burdened with being the primary caregiver for the hungry or the socially inclined. Patricia Prado-Olmos has watched the city morph during her nearly three-decade tenure at CSUSM, having spent the past six years as the school’s chief community engagement officer. She also just announced her forthcoming retirement at the end of the 2026–2027 school year, so she’ll have even more time to haunt local haunts.

Meet the Local: Patricia Prado-Olmos

Those in the know call the university “Cal State StairMaster” from the Sisyphean amount of stairs on the hillside campus. So, any day at or around CSUSM should start with a homestyle carbo-load (biscuits and gravy) from Mama Kat’s.

Rull, a Michelin-trained pastry chef who’s done stints on Netflix (Bake Squad) and Food Network (Super Mega Cakes, Halloween Wars), opened his patisserie last fall. The hype hasn’t cooled off yet: Get there early because the crowds do.