Sippin’ Santa at 55 South / Miracle on 1st in Downtown San Jose

The holiday season continues in downtown San Jose where two holiday cocktail pop-ups are still pulling in revelers. Both Sippin’ Santa and Miracle offer a variety of festive cocktails along with interesting and fun glassware that’s available for sale.

Sippin’ Santa at 55 South

We started at 55 South for Sippin’ Santa, the tiki-themed holiday pop-up produced with Jeff “Beachbum” Berry. The new cocktail and mug this year is Sharkey’s First Christmas, featuring vodka, aquavit, melon and walnut liqueur, lime and pineapple juices. Mrs. Mai Tai thought this was pretty good and I have to agree it was a nice twist and the mug is pretty good too. I had Sippin’ Santa cocktail that has Demerara rum, amaro, lemon, orange, and gingerbread mix – an all time favorite mug and the cocktail is always great too.

The team at 55 South did a good job with the drinks and decor again this year, though the music for our experience was a Sade playlist followed by mid-1950s rock ‘n roll hits. So, not really the holiday vibe. We arrived early and the crowd was sparse, but grew later in the evening.

55 South

Miracle on 1st is at Paper Plane across the street and continues to impress. The decor is elaborate here, and we found the service at the bar to be quite efficient and super friendly. I was driving and asked for something non-alcoholic and received a very nice juicy highball that was fantastic. Mrs. Mai Tai had the excellent Marshmallows & Unicorns, the complex cocktail with gin, several liqueurs, lemon, egg white, bitters, and cardamon. Our friends really liked their Carol Barrel and Hot Buttered Rum, two Miracle standouts. Crowds grew during our visit and there was a line when we left, so go early if you can.

Miracle on 1st at Paper Plane

Miracle has a larger cocktail menu than Sippin’ Santa and the more varied options seem offer something for everyone. Sippin’ Santa added a holiday spritz this year but we think the smaller menu is a deterrent for many potential patrons. Adding a couple more cocktails would help for 2024.

A Mixed Bag at San Diego’s Grass Skirt

Finally made visiting The Grass Skirt a priority. We thought that since it is all-ages at dinner time that it would work for our family trip, plus we were interested in experiencing Sippin’ Santa pop-up one more time this season.

Definitely a mixed bag.

Sippin’ Santa Holiday Pop-Up Decor

The decor here is pretty nice, but the music was nothing but reggae covers of pop songs. Which got old very fast and kind of ruined the Christmas vibe too. They also had sound system issues with their special effects. We do really dig their speakeasy entrance and there were some nice Christmas decorations up, though this is not as elaborately themed as some holiday pop-ups we’ve patronized.

Entrance to “Other World Travel”

We enjoyed the Shrimp and Pork Wontons, but overall didn’t think the food was that great here, with small portions and some odd choices (why does the tofu come with ground beef?). Our service was pretty good, and our server had a nice Christmas sweater on.

We ordered cocktails off the Grass Skirt menu rather than Sipping’ Santa, which in retrospect was overall a mistake. We didn’t care at all for the Clarified Painkiller (doesn’t taste like a Painkiller at all) or the Banana Berry Old Fashioned (barely any banana or berry flavors). The Tropical Soda needed more tropical flavoring. Boozing’ Susan’s World Famous Chi Chi did not live up to the hype in the name (like nearly all cocktails claiming to be “world famous” truth be told) and felt a little flat to me. Mrs. Mai Tai didn’t really like it at all and this type of cocktail is right up her alley.

Clarified Painkiller and Chi-Chi

Thankfully, I’m pleased to report that Tropical Tony’s Mai Tai was really good. A very nice rum blend and a nutty orgeat put this on my honorable mention list for best Mai Tai of the year. I would definitely return for this, one of the better Mai Tais in the city.

Nutty Mai Tai at the Grass Skirt

Sippin Santa at 55 South in San Jose

The annual holiday pop-up with a tiki theme is back at 55 South in San Jose. This craft cocktail bar and restaurant did the decor even more elaborately this year, and staff was ready to serve us at opening on Sunday. Music was peppy and got everyone in the mood.

Sippin Santa comes from the our favorite cocktail historian, Jeff “Beachbum” Berry, in partnership with Cocktail Kingdom that also runs the Miracle pop-ups (including two downtown San Jose locations within a 5 minute walk of 55 South, Paper Plane and Miniboss).

This year the Mersanta mug is available for sale after the cocktail debuted on the menu last year. Such a cute mug, and the cocktail with tequila, applejack, and maple-cranberry syrup is quite a delight. I went with the classic Sippin’ Santa cocktail that has Demerara rum, amaro, and gingerbread mix. Really great, and prices for both the cocktails and merch are pretty reasonable.

Sippin’ Santa Cocktail

A new drink this year is Island of Misfit Toys, featuring Jamaican Rum, Chai Tea, cream, cinnamon, and pumpkin puree. If you like Pina Coladas and Pumpkin Spice, this will be your new all-time favorite. I like both, as does Mrs. Mai Tai, so this cocktail is right up there with Sippin Santa’s Kris Kringle Colada as something to go out of your way to try.

55 South has a pretty decent food menu. I enjoyed the Shrimp Roll and we all looooved the Cream Cheese Bread, a small loaf of Olive bread covered with cream cheese. Probably the best thing in the entire building.

Sippin’ Santa at 55 South in San Jose

The Christmas/Tiki themed pop-up has been gaining momentum over the past few years and is expanding to new locations. This year, downtown San Jose is in the mix thanks to 55 South who are hosting the pop-up for the first time (view menu). A cocktail bar and restaurant, 55 South had previously hosted monthly “tiki nights” that served as sort of gathering place for some South Bay locals who have been underserved for tiki for so long.

The 55 South team did a pretty good job with the decor. Quite festive and for sure plenty good for the first year to get everyone in the mood. Music was 70s-80s leaning Christmas music, so quite peppy.

Cocktails for Sippin’ Santa are developed in conjunction with Jeff “Beachbum” Berry (of Sippin’ Safari book fame). I had the Kris Kringle Colada, an excellent riff using Dark Jamaican Rum, Amaro, and Allspice, while Mrs. Mai Tai ventured away from her coconut sweet spot to try the Sippin’ Santa with Demerara rum and citrus. Unfortunately that one seemed to be lacking the “Gingerbread mix” that makes it a holiday favorite.

Nonetheless we had a great time and the bar was quite busy even at opening on a Sunday. I had the “Tiki Tacos” that were quite good, and Julie liked her Edamame Salad. The meetup was for members of the “South SF Bay Area Tiki Ohana” group on Facebook. If you’re a local, please join the group for more meetups and local info.