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Local summer is in full swing in Little Italy! As the late-summer weather cools down, it’s the perfect time to book a local staycation and explore what the neighborhood has to offer this month. With top-tier stays just walking distance from all the action, locals are invited to settle in and experience the charm of Little Italy for themselves.

Where to Stay For Your Local Summer Staycation

There is no shortage of locally loved accommodations in Little Italy. For a sleek and modern stay, Carté Hotel offers an experience for those who love the finer things in life. Just down the road, Porto Vista is a retro-chic hideaway for artistic souls. Or, for a classic waterfront stay, the Hilton Bayside has ocean-view rooms that you’ll never want to leave, while the Courtyard by Marriott and Urban Boutique Hotel provide comfortable stays for the family. No matter what your staycation vibe is, Little Italy has a place for you.

The best part about the hospitality of Little Italy? There is a never-ending list of things to do. If you are new to the area, hop on one of the Little Italy tours. For a picturesque Saturday stroll, explore the Little Italy Mercato, where dozens of vendors come together for one of San Diego’s favorite traditions. Take in the smell of locally baked bread while browsing handmade artisan crafts or take a seat at one of the family-owned Italian restaurants that line India Street.

Little Italy Labor Day Stickball Classic

Step into a Little Italy tradition this Labor Day weekend at the Little Italy Labor Day Stickball Classic, happening Saturday, September 5th through Monday, September 7th from 8:30 am to 6:30 pm. A Little Italy staple for more than three decades, the tournament keeps the old-school game of stickball alive while celebrating the community and generations who have made it a neighborhood favorite. For more information, please visit www.littleitalysd.com/events/labor-day-stickball-classic.

Punches in the Piazza

Punches in the Piazza is one of those Little Italy traditions you can’t find anywhere else. Hosted by the Bobby D. Foundation on September 11th at 6:00 p.m., this event combines amateur boxing, philanthropy, and a powerful tribute to the 25th anniversary of 9/11.

“There’s an unmistakable energy that comes from bringing people together for a cause bigger than themselves. Hosting Punches in the Piazza at the Piazza della Famiglia allows us to create an exciting night for the community while making a meaningful impact for those who need it most,” said Michelle DePhillipis, founder of the Bobby D. Foundation. On top of USA Boxing-sanctioned amateur bouts, guests will enjoy silent auction opportunities, raffle prizes, and more for a truly memorable night.

State of the Neighborhood

On Thursday, September 24th from 5:30 pm to 9:00 pm, the State of the Neighborhood will be hosted on the rooftop lanai of Kilroy’s premier office building. Come together for a night of community togetherness where neighbors, business owners, residents, and visitors can wine and dine in the heart of Little Italy. Learn about current happenings and future projects to come. Plus, show up early for happy hour to mix, mingle, and meet new people!

For the latest updates, please visit littleitalysd.com or follow us on Instagram @littleitalysd.