Romantic Weekend in San Jose for the Holidays
Romance is extra special in the city around the holidays, and we’ve handpicked some of our favorite seasonal activities for you to share with your sweetheart! Here's a 48 hour itinerary.
Day One
Morning
After a peaceful night’s rest in your suite at Hotel Valencia Santana Row, a Mediterranean-inspired luxury boutique hotel in West San Jose’s charming entertainment district, it’s time to begin the day with exquisite pastries and hot coffee at Cocola, just steps from the lobby doors.
Santana Row boasts some of the best shopping in the city, and the holidays are an extra-special time to visit. In addition to high-end retail stores, you’ll find festive decorations, live entertainment, and seasonal events like Santana Row Snow Showers, where the magic of the North Pole lands in San Jose!
Afternoon
Drop off your shopping bags in your room and grab your coat because it’s time to head downtown! Petiscos in the SoFa District is a Michelin Bib Gourmand recipient, perfect for a romantic lunch. Like tapas in Spain, petiscos are a Portuguese tradition of smaller shareable dishes like shrimp fritters, arroz de pato (duck rice) and caldo verde (kale soup).
After lunch, how about some wintry ice skating in sunny California? Downtown Ice is returning to the Circle of Palms Plaza, between the Signia by Hilton Hotel and the San Jose Museum of Art. Visitors can book 90-minute sessions to glide and twirl on the outdoor rink. Afterward, you can walk to nearby attractions like Winter Wonderland (a festive holiday carnival with rides and games), and Christmas in the Park (an annual installation of trees, lights, and artwork by local nonprofit groups).
Evening
It’s time to visit a San Jose icon: The Winchester Mystery House. This 100-year-old mansion guides visitors on tours through its haunted maze of rooms, and their seasonal Saturday night Candlelight Tour is an open-house-style walk through with seasonal stories from staff, and stunning Victorian Christmas decorations.
Later, head back to Santana Row for dinner at Left Bank Brasserie, a fusion of classic French cuisine and local, seasonal California ingredients. Choose from an extensive wine list or sip an innovative cocktail from the American Bar.
Day Two
Morning
Begin your day with a walk through the Municipal Rose Garden, nicknamed "America's Best Rose Garden." With more than 3,500 plantings and 189 varieties featured, this garden will make your stay here in San Jose even more romantic.
Afternoon
After a stroll through the Rose Garden, make your way to one of Downtown San Jose's four historic theaters — The California Theatre, Center for the Performing Arts, San Jose Civic, and Montgomery Theater. There are plenty of holiday performances at each theater including Symphony San Jose's Holiday Spectacular and the San Jose Nutcracker!
Evening
After the perfromance, enjoy a ten-minute stroll up First Street to nomikai, for a unique take on local and international cuisine complemented by a comprehensive “drinkery” menu with premium Japanese sake, craft spirits, beer, and wine. Hot honey linguica sausage pizza, spam musubi, and Brussels sprouts with creamy miso round out their eclectic and innovative menu.
Finally, hop a ride to PayPal Park (home of the San Jose Earthquakes) for Enchant Christmas, a one-of-a-kind immersive experience. Explore the story maze glowing with Christmas lights, window shop through the holiday village full of artisan boutiques, glide along the ice-skating trail and even meet Santa himself! Sip Champagne and share a kiss with your love, as holiday music plays and the stars light up the sky.
