San Diego in May 2023

“What you get by achieving your goals is not as important as what you become by achieving your goals.”

―Zig Ziglar

San Diego is such a beautiful city with so much to see and so much to do!

There are numerous activities available in San Diego in May. Winter rains will no longer be an issue, and June Gloom at the beaches won’t typically start until much later in the year. Tourist destinations are less crowded than they will be because the summer vacation season hasn’t yet begun.

You can take Mom on a memorable day in May or celebrate Cinco de Mayo with San Diegans on May 5. Summer officially begins with the three-day Memorial Day weekend on the last Monday of the month.

Each month I have special fun events I want to show you so that you get the most out of this beautiful city!

Fiesta Old Town Cinco de Mayo

Enjoy sizzling flamenco beats and Mariachi Music and tons of food and drinks. Location: Old Town, San Diego Avenue (between Conde and Twiggs). Info: 4/30, 5/1 Sat 10 am – 10 pm, Sun 10 am – 6pm


This annual pawty features photo ops, pop-up shopping, beer for people, and pups!
Location: Second Chance Beer Company. Info: 5/4 12 – 4 pm

Taste of Cardiff

Celebrate the culinary flavors and locally crafted libations that make downtown Cardiff district so unique. Location: various. Info: 5/4 5:30 – 8:30 pm

FoodieLand Night Market

A foodies will find 190+ vendors, a variety of amazing foods, games, and entertainment for the whole family. Location: Del Mar Fairgrounds. Info: 5/5 – 5/7 Fri 3 – 10 pm, Sat & Sun 1 – 10 pm

Free Comic Book Day

A committee of comic shop retailers chose 43 titles for fans to discover! Location: participating comic bookstores. Info: 5/6 various hours

Clairemont Garden Tour

The CTC’s Garden Tour showcases beautiful private gardens throughout the Clairemont Community. Location: various in Clairemont, Bay Park, and Bay Ho. Info: 5/6 10 am – 4 pm


Celebrate the pure magic that tacos offer to the world, at ‘Reader Tacotopia 2023’! Location: Golden Hill Park. Info: 5/6 2–5pm

Carlsbad Village Faire

Over 750 unique vendors with a little of everything: arts & crafts, antiques, unique clothing, items from around the world, and more. Location: Carlsbad Village Dr. Info: 5/7 8 am – 5 pm

Gator by the Bay

Celebrate the music, food and culture of the Louisiana Bayou. Zydeco and Blues, Creole food, and Crawfish. Location: Spanish Landing Park, Saturday Night Dance at the Sheraton Hotel Ballroom. Info: 5/11 – 5/14 Thu 6 – 10:30 pm, Fri 4 – 10:30 pm, Sat 11 am – 8 pm, Sat Dance 9 pm – 12 am, Sun 11 am – 7 pm

Crystal Pier Outrigger Race

The race draws 1500+ participants annually who battle in a 6-mile short course, novice and kid’s race as well as a 10-mile men, women and coed races in six- person outrigger canoes. Location: Crown Point. Info: 5/13 7 am

Relive Beatlemania

Get ready to “Relive Beatlemania!” with So Cal’s very own foremost Beatles tribute band Britain’s Finest. Location: Fallbrook Mission Theater. Info: 5/13 6-9pm

Bike Anywhere Day

Whether you are a student, commuter, bike enthusiast, or someone who is new to biking, pledge to GO by BIKE anywhere. Location: San Diego. Info: 5/18 pit stops open from 6 am – 9 am

San Diego Fringe Festival

This festival allows artists to showcase their works and performances in a setting unconstrained by censorship, judgement, or the status quo. Location: various. Info: 5/18 – 5/28 various show times

La Jolla Half Marathon & Shores 5K

One of America’s most picturesque and beautiful point-to-point races. Location: Del Mar Fairgrounds. Info: 5/20 6:30 am

OB Kite Festival

Enjoy kite building & decorating, prizes, pro kite fliers, demonstrations, games, and more. Location: Robb Field. Info: 5/20 10 am – 3 pm

Island Vibe Music Festival

Enjoy unique cultural dancers, a vendor village, art, apparel, and food. Location: Surf Cup Sports Park, Del Mar. Info: 5/20 1 – 8 pm

42nd Annual Fiesta Del Sol

This free beachside music festival features The English Beat, Iya Terra, and more! Location: Fletcher Cove, Solana Beach. Info: 5/20 – 5/21 Sat 9 am – 10 pm, Sun 9 am – 8 pm

Navy’s Original Bay Bridge Run/Walk

A run/walk across the Coronado Bay Bridge is a rare opportunity! Location: Downtown to Coronado. Info: 5/21 8 am

Santee Street Fair

This is a free, public event featuring vendor booths, food, and entertainment. Location: Riverview Pkwy. & Town Center Pkwy. Info: 5/27 10 am – 6 pm

North Park Music Fest

A music venue, art gallery, and food festival all rolled into one. Location: North Park Mini Park. Info: 5/27, 5/28 Sat 11 am – 10 pm, Sun 11 am – 9 pm

As always, if you or anyone you know needs assistance buying or selling or if you have any real estate questions, please feel free to contact me by phone, text, or email! 

So much to do, so much to see!

If you want to see a home sometime this month, check out all my Featured Listings, and message me or contact me here.

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