Winter Splendor at Cielo Rooftop: San Jose's Elevated Holiday Escape

Cielo has always been one of my favorite secret spots to take visitors up to when visiting Santana Row. It's hidden at the very top of Hotel Valencia and overlooks Plaza de Valencia with the Santa Cruz Mountains in the background. It's often open to enjoy the view, but is underutilized as a place to grab a drink or bite for most of the year. Fortunately, that is changing with it's very first Winter activation: Cielo Rooftop's Holiday Experience.

This reimagines Cielo as a cozy winter wonderland until January 10, 2026 featuring frosted pines, glowing fire pits, and plush seating draped in faux fur. Open Tuesday through Saturday from 5 to 9 p.m., the space creates an intimate outdoor retreat perfect for sipping drinks amid the city's soft evening lights. Closed on Sundays, Mondays, Christmas Day, New Year's Eve, and New Year's Day, and it operates weather permitting.

The experience also features an exclusive partnership with Piper-Heidsieck Champagne, highlighting bespoke cocktails, caviar pairings, and premium pours available by the glass or bottle. Menu selections include starters like butternut-coconut soup with vegetables or spicy chorizo croquettes, shared plates such as Spanish charcuterie with cheeses and cured meats, and entrees ranging from chickpea ratatouille with spinach and mozzarella to volcano lamb shank with spicy carrot puree with pickled red cabbage.

I was invited to sample the menu last week and thoroughly loved the experience. The warm butternut-coconut soup was perfect for a winter night and I would highly recommend having it with the optional braised beef. The spicy chorizo croquettes and volcano lamb shank are also a must. I practically licked the bone clean on the lamb.

Desserts round out the offerings with apple pie and a killer chocolate fondue with marshmallows, nuts, and fresh fruit. It's perfect for sharing on a date or with a group of friends.

I would also recommend trying the mulled wine, which is a seasonal drink that is not easy to find in the Bay Area. Seasonal cocktails include a spiced mule with pear vodka; the Santana 75 with gin, lemon, raspberries, and Piper-Heidsieck 1785; and a Hot Toddy with bourbon, honey, and lemon juice.

A $50 food and beverage minimum per person applies, which is very reasonable given the quality and uniqueness of the Cielo Rooftop's Holiday Experience. Since winter weather can be unpredictable, all seating is on a first-come, first-served basis. Amenities like space heaters, blankets, and hand warmers are available for guests. Bundling up is still recommended to get the most out of your night out, but it was a very cold night when I went and we were never uncomfortable thanks to the heaters.

I would highly recommend checking this out this holiday season. Try to get there early as they have been completely full on multiple nights. To get there, you have to head up to the Hotel Valencia lobby, then take a second set of elevators used for the hotel rooms up to the 7th floor. For more details, please visit https://www.hotelvalencia-santanarow.com/holidays-on-cielo-rooftop.htm.