10 Festive Places to Eat, Drink and Play in San Diego this Holiday Season

It’s the greatest time of year in San Diego. While I’m a summer lover, nothing compares to the holidays by the beach. The bars, restaurants, and hotels are decking the halls, and I’ve curated a list of the top 10 festive spots in America's Finest City to eat, drink, and play. From cozy eateries adorned with twinkling lights to spirited bars serving seasonal cocktails in fancy mugs, immerse yourself in the vibrant holiday spirit with my recommendations for an unforgettable experience in San Diego this winter. Because this is my blog, trust these are the spots that are worth the hype this season.

Here are the 10 Festive Places to Eat, Drink and Play in San Diego this Holiday Season:

1) Drinks at Raised by Wolves

One of my favorite speakeasies, tucked behind a revolving door in UTC, decks the halls during the holidays. The cocktails here are really good (and strong), so consider taking an Uber for this one. After sipping a holiday cocktail, check out UTC’s Peppermint Beach Club and then head to Lucrezia for dinner. This restaurant quickly climbed my rankings for one of the top Italian food options in San Diego.

2) Drinks at Miracle at Draft

Miracle does it again with its Christmas Bar decorations. Draft at Belmont Park is covered in head-to-toe decor, and you’ll be able to enjoy it without waiting in line for three hours like you would at Polite Provisions. The drinks are better here, too, in my opinion. They offered a lot of diversity in the flavor profile, and the biggest plus is that Draft has a full food menu, too.

3) Drinks at Fort Oak and Dinner at Cardellino

Last year, over the holidays, I tried Fort Oak for the first time and was so pleasantly surprised. We had dinner reservations at Cardellino across the street and decided to grab a drink before our reservation. The drinks here were incredible, and the Tuscan Experience was one of the most delicious meals of my life. Don’t sleep on this festive and delicious bar & restaurant pairing.

4) Dinner and Drinks at Grass Skirt (Sippin’ Santa)

While I don’t visit Grass Skirt often during the year, I find it a bit expensive for the portion sizes, I think this is a must-visit during the holidays. The holiday drinks are pretty tasty, and they go all out on the decor. I like going with one or two friends to order a bunch of things and split them. It’s close to the other bars in PB, so it’s a great spot to kick off the holiday bar frolic.

5) Dinner and Drinks at Craft & Commerce

This year, I visited Craft & Commerce for the first time with holiday decorations. In a few words, I’m OBSESSED. I forgot how good the food and drinks are here. As I’ve started drinking less, I’m very particular about cocktails. C&C slays with the drinks. I got the Songbird, a spicy cucumber tequila drink, and my friend ordered the Winter Rush, a holiday version of the Gold Rush. The Mac and Cheese is to die for, so add that to your order. False Idol, the speakeasy behind the restaurant, is also decorated for the holidays if you want to keep the evening going.

6) Dinner at Cesarina

Cesarina always hits the spot, but the dinner experience is extra enjoyable during the holidays. They don’t have any unique holiday specials, but the patio and indoor decorations will get you in the spirit. Dinner reservations are tough to get now that the temporary front patio from the pandemic is gone, so book ahead or visit during lunch/brunch to enjoy the decor with the sun out.

7) Bottomless Brunch at Duck Dive

Something about going to brunch in an elf onesie feels right? One of my favorite holiday activities is to dress up in our holiday best and make a reservation at Duck Dive on the same day as the PB Holiday Parade. Everyone’s out, dressed up, and bar hopping. It’s a really fun and festive day.

Pro Tip: Eat a heavy breakfast at DD. The cheap champagne will catch up to you.

Now that we’ve covered the best places to eat and drink, let’s chat about activities around town.

8) Dinner at Serea and Skate at the Hotel Del Coronado

The Hotel Del’s iconic ice skating rink faces the ocean; there's nothing more San Diego than that. While I find the skating to be a bit overpriced, you should do it at least once to check it off your San Diego bucket list. While you’re down there, head to Serea for a delicious dinner. They recently rolled out Igloo Dining in front of the skating rink, so I’ll need to check that out and report back.

9) Sip and Explore Winter Wonderland at Lakehouse Resort

I was excited to have the opportunity to explore the Lakehouse Resort’s Winter Wonderland and Igloo Experience this year. While the igloos didn’t live up to the hype (2 bottles of wine and a subpar charcuterie and dessert board are not worth $600, IMO), the Winter Wonderland did! For only $5, you can pay to walk the grounds, see the lights, and go on a candy cane cruise around the lake. The Winter Wonderland has a cocktail cabin where you can purchase drinks and activities for kids, like a bounce house and train.

10) Lightscape at San Diego Botanic Gardens

Last but certainly not least, head to Encinitas to check out the Botanic Gardens. They put on quite the Lightscape, that you can walk through and see all kinds of holiday lights. We braved the rain for this one, and it was still worth it, in my opinion. This is a really cute date night idea or family-friendly activity. They have snack and drink stands throughout, so you can sip and stroll.