8 Fun Date Ideas: Weekend in San Diego

Kevin and I just got back from spending a romantic weekend in San Diego. Next year, we’ll be getting married in downtown Los Angeles. However, we hired a photographer based in San Diego who offered to snap some photos of us for free if we came to him. Now who can pass up a freebie?

We packed our bags, dropped off the kid (i.e. the dog) at the sitter, got a hotel and planned out our weekend. Okay, guess it wasn’t EXACTLY free. Minor details! If you’re looking for some fun date ideas without the kids (or the dog), check out our top recommendations below.

8. Dinner in Little Italy

No trip to San Diego is complete for us without stopping along India Street in Little Italy. Once home to San Diego’s flourishing tuna fishing industry and generations of Italian families who made their living on the sea, Little Italy is now a lively neighborhood filled with patio cafés, packed restaurants, craft brew stops, art galleries and gift shops, boutique hotels and Amici Park. You won’t leave hungry – and some of our favorite must-stops include Assenti’s Pasta, Mona Lisa Italian Foods and browsing the Japanese ceramics and gifts at Vitreum Giftware. For a relaxing sit down meal, check out Barbusa, located right in the heart of Little Italy. They have an extensive drink menu, but our favorite part? The free house bread! It’s like getting a mini pizza. And we had no shame eating 3 of them. Okay, maybe a little shame after we ate them all!

7. Wine Tasting in the Hillcrest Neighborhood

Located in the hip/walkable neighborhood of Hillcrest you’ll find The Wine Lover. It’s a tiny spot, but exactly what we were looking for as we strolled around the neighborhood.  We grabbed an outdoor table and sipped on some champagne and chowed down on some bruschetta. We pretty much had the entire place to ourselves (since it was closing time).  The guys who run the place are hilarious, and more than willing to help you out in your selection or let you try a few before deciding.

6. The Lot Movie Theater

Another favorite must-stop on our San Diego route is The Lot movie theater. It isn’t cheap at $20+ per ticket. But we love these high-end premium movie experiences for a special date night. This place is fancy – each theater has cushioned reclining chairs and a full menu with drinks you can order inside while you watch your movie. There are two locations — one in La Jolla just North of San Diego and the other at Liberty Station in San Diego. There isn’t much of a difference between the two theaters, but we ended up going to La Jolla this time since Liberty Station was all sold out. Reserve your seating a few days in advance if you’re going on a weekend (insider tip from us!).

5. Saturday Mercado (Farmers Market) in Little Italy

Another trip to Little Italy – you know where we spend most of our time! On Saturdays, though, you will not want to miss the massive Little Italy Mercado with plenty of free samples and local products galore. We recommend trying to be an early riser for this (which we are not!). The market opens at 8 AM, which is the best time to avoid the post-workout/beach goer rush. This place can get overly crowded especially around the lunch period.  Besides all the delicious food stands, we recommend getting breakfast at the open-air Lofty Coffee Co. They have a wide range of healthy options like the Ancient Grain Faro Bowl. Or whatever, you can just get the cinnamon rolls!

4. Apple Farms in Julian

This next stop will take you out of San Diego – but it’s still pretty close (and worth it). Located about 1 hour 15 minutes from downtown San Diego is the mountaintop town called Julian. The place is known mostly for two things — gold mining and apple picking! And where there are apples, you’ll find apple pie. In fact, you’ll find an entire stretch of bakeries where you can sample several. If you’re visiting during the fall, you should make a beeline to Volcan Valley Apple Farm where you can pick your own bag of apples for $13 (for two people). We’ve gone other years and the trees were pretty much empty.  Not the case this year.  I literally was eating about every other apple I picked along the way. Next, head into downtown Julian (2 minutes drive) where you can shop (yes!) and buy some apple pie and ice cream.  Kevin and I have ate at EVERY bakery over the years.  And we both agree that the pies at Julian Pie Company are the best. Especially if you get it with cinnamon ice cream! There are lines at every shop, but this one is worth the wait.

3. Maritime Museum

The Maritime Museum is way cooler than it sounds. Located along the waterfront (not too far from Little Italy!), you’ll feel the breeze and re-live your pirate or boating dreams here.  Plus, it’s open super late — all the way to 8 PM in case you want to explore other things during the day.

This floating museum could easily be a snoozefest. But we never got bored once.  Kevin didn’t even fall asleep!  A true sign of a good museum.  Exhibits stretch across 5 boats and you’ll need to be in decent shape to climb through. I thought about visiting this museum while on crutches, which would have been really tough.  The museum has a collections of historic ships, including the world’s oldest active ship called the Star of India. Inside, they re-create life on board where families took the 6 month journey from England to New Zealand to set up a new life. The bathroom situation alone would have convinced me no trip would be worth it!

For those not adverse to tight spaces, you’ll want to go inside the Russian Foxtrot-class submarine with an exhibit inside about the 1962 Cuban Missile Crisis. No lie, you’ll get a workout inside and they even have portal holes outside the ship to test whether you can actually make it through the sub.

2. Cinema Under the Stars

A hidden gem and perfect date night — located in the Mission Hills neighborhood — is Cinema Under the Stars. Reserve your seats in advance as this tiny outdoor theater typically sells out each night. And it’s mostly the classics here — the night we went they showed the Alfred Hitchcock film Notorious. The theater has walls with an open roof (hence the “under the stars” part). We recommend grabbing the zero gravity chairs and lounging back (or the love seats if you get chilly and want some body heat).  The theater also includes blankets, which were definitely needed the night we went!  Tickets are $16 for members, $17 at the box office and $19 with online reservations (cash or check only).

1. Speed Boat Adventures

Hang on tight! San Diego Speed Boat Adventures is one of the best things we’ve done.  Okay, full disclosure, we’ve never driven a speed boat.  And signed away our lives on the waiver without thinking twice.  This trip will either be the best date idea ever — or maybe an indicator of how crazy the other person is.  In our case, we probably would have not passed the crazy test.  We had two speeds: fast and ‘we’re gonna die’ fast.’  The tour is about 1 hour where you zip around the harbor (following a guide).  Halfway through, you’ll get to switch out with your partner.  Basically, it was an hour where each of us felt like we were going to have a heart attack as the other person drove. Amazingly, we didn’t run into anyone, fall out of the boat or flip over.  All scenarios I played out at least every 2 seconds on our jet boat ride.  We loved it, and at $70 pp in a double boat, you can’t miss it!