Weekend Getaway: The Best San Diego Date Ideas

Aug 6, 2016

This is the first in my “weekend getaway” series, where I describe some great weekend trip date ideas.  The first destination I’m going to talk about is San Diego. Only a few hours away from Los Angeles, (depending on traffic), San Diego is an ideal weekend date destination.

I hadn’t been there in years and recently returned. I was impressed at how many fun things there were to do down there, as well as how romantic it was.  I’m not a San Diego native, but these are the highlights from my recent trips to San Diego that I’d recommend to you.

1. Balboa Park

One of the crown jewels of San Diego (and of all of California) is Balboa Park, the nation’s largest urban cultural park. Among its attractions are fifteen major museums, the world-famous San Diego Zoo, the Ruben H. Fleet Science Center with IMAX theater, many botanical gardens, and all-around beautiful and romantic grounds.

Casa del Prado, Balboa Park

Casa del Prado, Balboa Park

The park as it appears today had its beginnings at the 1915-16 Panama-California Exposition commemorating the opening of the Panama Canal. The buildings were built in the Spanish Colonial Revival architectural style. Unfortunately, they were only intended to be temporary, so they eventually had to be re-built to be more permanent, but the look was preserved.

Balboa Park

Balboa Park

You can pay to take in the museums and other offerings, or not pay a dime and still have a good time here. Go for a jog, or just walk around and take in the surroundings. Admission to the grounds and Botanical Building (which is a must-see) are free! All of this makes Balboa Park a “must-see” daytime attraction on your visit to San Diego.

Just west of Balboa Park, over the bridge, is a great Italian restaurant called Cucina Urbana. I was a little hesitant when the waiter recommended the grilled octopus appetizer, but it was amazing!

2. Hotel del Coronado

Another “must-see” if you’re visiting San Diego on a date, is the Hotel del Coronado. Opened in 1888, it was built to be the ultimate luxury resort, featuring fishing, hunting, boating, bicycling, swimming, golf, and of course, fine dining. 1958, it was made even more famous when the Marilyn Monroe movie, “Some Like it Hot”, was filmed there.

Hotel del Coronado

Hotel del Coronado

Today, it’s still one of the most romantic spots in Southern California. It’s very expensive to stay at the hotel, but you can always just stop by for lunch or dinner, or just to walk the grounds and browse the many shops there.

W dined at the finest restaurant there, 1500 Ocean. It was not crowded on a Sunday night. The food and service were impeccable.

Roasted Duck at 1500 Ocean

Roasted Duck at 1500 Ocean

After dinner, stroll along the beach and view the hotel from afar.

Coronado Beach

Coronado Beach

Parking is very expensive at the hotel (especially if you don’t buy anything there), but if you’re willing to walk a block or two, you can often find parking on nearby streets.

3. The Gaslamp Quarter

The Gaslamp Quarter in the middle of downtown San Diego really makes me jealous. I wish Los Angeles had a downtown area that had so much going on, which was as safe, clean, and walkable. (Downtown L.A. is getting there slowly).

US Grant Hotel across from Horton Plaza

The US Grant Hotel across from Horton Plaza is worth a visit if you’re interested in history

There are tons of great restaurants, bars, and dance clubs there. During the early evening it’s more of a quiet dinner scene, whereas on weekend nights it becomes a hot spot for dancing and bar-hopping.

A San Diego native friend of mine recommended Meze as the best restaurant there, and it did not disappoint! We had Greek dishes there that I’ve not found anywhere else (try the flaming shrimp!)


Meze Greek Restaurant

The Gaslamp District is also home to Horton Plaza, which features occasional free outdoor performances, and is adjacent to a shopping mall.

When I go to San Diego, I like to stay at a hotel that is within walking distance of the Gaslamp Quarter. I like the trendy Bristol Hotel because it’s at the edge of the Gaslamp Quarter, away from the craziness that happens there, yet close enough to walk to it.

4. La Jolla

San Diego has so many wonderful beach towns around it. One of these is La Jolla, just 14 miles north of the city.

The beach at La Jolla features a beautiful rocky shore filled with sea lions which seem to be fearless when it comes to interacting with people (but of course – keep your distance for their protection and yours).

Rocky shores at La Jolla

Rocky shores at La Jolla with fearless sea lions

You can also go on guided group kayak tours of the famous caves.

If you’d rather not get wet, go to the The Cave Store gift shop with a sign that says “Sunny Jim Cave”.  You can pay five bucks to walk down a man-made tunnel to one of the waterfront caves. It’s famous for its devil-shaped silhouette (or is it a hipster with goatee and man-bun?)  It’s not a huge attraction but it’s worth it!

Sunny Jim Cave in La Jolla

Sunny Jim Cave in La Jolla

La Jolla also has some amazing restaurants. Not all cost an arm and a leg either. To sample some of San Diego’s famous tacos (with a twist), go to Puesto a few blocks inland from the shore.  The soft tacos there are amazing!

Puesto in La Jolla

Puesto in La Jolla

For all of these reasons, I’d say a stop in La Jolla is a “must” on your way to or from San Diego.

5. Kayaking

San Diego has some great urban kayaking spots. I’ve already mentioned La Jolla, which has group kayaking tours of its famous sea caves.

Kayaking in La Jolla

Kayaking in La Jolla

During busy weekends, advance reservations are suggested.

Another very popular kayaking spot is Mission Bay, where you might catch a show at Sea World if you’re lucky! There are many katak rental shops surrounding the bay.

Finally, you can kayak in San Diego bay, with rentals at the Coronado peninsula.

6. Seaport Village / Waterfront Park

Not too far from the Gaslamp Quarter is Seaport Village. I’d describe it as a much bigger, better, and more lively version of Marina del Rey. When I went there were a ton of people out and a live band playing in the courtyard. There are tons of shops and restaurants of course.

But for me, the real highlight of this area was just to the north, at the USS Midway Museum. The Midway is an aircraft carrier, commissioned just a week after the end of World War II. It was the largest ship in the world until 1955, and it’s still an awesome sight. I didn’t even go aboard; just walking around it was impressive! But of course they offer tours if you’d like to explore!

USS MIdway aircraft carrier

USS Midway aircraft carrier

There are other vessels to see, including the B-39 Soviet submarine, the USS dolphin, an American submarine, and the Star of India, the world’s oldest active sailing ship. All of these can be boarded with paid admission.

Star of India

Star of India

7. Little Italy

San Diego has lots of cool little neighborhoods with great restaurants. One of these is Little Italy. It’s pretty small, but offers some great restaurants and nice evening strolls.

Little Italy

Little Italy

One unique dessert destination there is iDessert, featuring a unique hard-shelled gelato-filled meringue dessert that you customize on iPads.


Hard-shelled Meringue desserts at iDessert. It’s a novelty that you can’t get anywhere else.

8. Old Town

While some would describe San Diego’s Old Town as a tourist trap, there are some great attractions here. You’ll find fantastic Mexican restaurants nearby and historic charm at Heritage Park, featuring restored Victorian homes.

We had dinner at Old Town Mexican Cafe, which featured hand-made tortillas and great ceviche. There was a wait to get in, but it was worth it.

If you want somewhere with a more romantic ambiance, check out the Cosmopolitan Hotel and Restaurant. Dining here is a unique and charming experience!

9. Petco Park

Even if you’re not a Padres fan, Petco Park is a worthy destination if you’re a baseball fan because it’s a clean, beautiful, modern stadium.  Of course, food prices are pretty outlandish, but you can have a great meal at one of the restaurants in the Gaslamp District, then simply walk to the stadium!


There are so many other great attractions in and around San Diego. I’ve only scratched the surface of the many great things to do there. It’s definitely worth the drive from L.A. or Orange County and it makes me jealous of their great beaches, restaurants, museums, and neighborhoods.

If you have a favorite destination in San Diego, please tell us about it in the comments! – Brian

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