San Diego, California has long been on my list. We finally made it happen as a long weekend getaway to celebrate our eighth wedding anniversary.

After mapping out our itinerary, we decided we’d book a place to stay downtown for our first two nights and then along the coast in La Jolla for two nights. Choosing a place to stay downtown was quite the feat, but we ultimately used our Chase rewards points to stay for free in Little Italy.

We ended up loving the Little Italy district! I wasn’t sure when we initially arrived because we got in very late on a Friday night, and people – and loud music – were everywhere. We are not into the nightlife/club scene and I was very afraid we’d made a poor choice, but as luck would have it, our hotel was just on the edge of the chaos. We had a quiet night’s sleep and in the morning we set off to explore a vastly different side of the neighborhood.

San Diego’s Little Italy has been around since the 1920s and is the city’s oldest continuous neighborhood business district. It survived the decline of the tuna industry and significant loss and destruction during the construction of I-5, however in the 1990s the locals began a revival that resulted in today’s thriving community of amazing restaurants, shops, and accommodations.

Our hotel was only a few blocks from the heart of Little Italy – Piazza della Famiglia.

The central gathering point in Little Italy is a European-style piazza known at Piazza della Famiglia. The 10,000-square-foot plaza connects India and Columbia streets and features a dramatic tiled fountain. Enjoy an afternoon stroll across the cobblestone street while relaxing before dinner.

https://www.sandiego.org/explore/downtown-urban/little-italy.aspx

I was expecting things to be quiet as people recovered from the night before but the plaza was bustling with a blocks-long farmer’s market underway! We had looked up a place for breakfast and were shocked to find that the line roped all along the farmer’s market stalls – so much for arriving early!

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As it turned out, the restaurant we were interested in – Morning Glory – had just opened so the line to get in (and then to make reservations to get in) moved fairly quickly. We heard them telling some larger groups ahead of us that it was a multiple hour wait, but when we said we were willing to take the first available seating, we were told it would be less than 30 minutes.

We wandered around the farmer’s market while we waited and before we knew it we were grabbing some stools along the outdoor bar and trying to split our attention between the amazing menu and the incredible decor. (Please note the giant eyeball in the picture below – it would blink and look around, which was both creepy and cool!)

Brian ordered a bloody mary with a whipped celery foam on top and I ordered a maple latte – the first one I’ve seen on a menu outside Tree City Coffee! – and before we knew it we were chowing down on the breakfast fried rice and khachapuri – YUM!

Highly recommend this place for breakfast/brunch – go early!

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After a fun day exploring the San Diego waterfront and Coronado Island, we decided to return to Little Italy for dinner at Ironside Fish & Oyster Bar.

Thanks to COVID-19, it has been so long since we’ve been in any major cities that I seem to have completely forgotten that popular restaurants require reservations – whoops! There was a long wait but it ended up being well worth it – the food and atmosphere were incredible.

May I recommend the oysters in the half shell (duh), cucumber and melon salad (divine) and octopus a la plancha (delicious). So. Good.

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While we were waiting on our table, we walked around the main plaza and admired how the area transformed after dark.

The farmer’s market stalls were gone and replaced with open air seating, twinkling lights, and laughter and live music. It was the perfect end to our perfect time in San Diego’s Little Italy district!