Romantic Weekend in San Jose for the Holidays
’Tis the season for cozy dates and holiday magic! Whether you’re new loves or longtime sweethearts, this 48-hour San Jose getaway is packed with festive ways to celebrate together.
Day One
Morning
Wake up at Hotel Valencia, a Mediterranean-inspired luxury boutique hotel in West San Jose’s charming Santana Row shopping district. When you're ready to start the day, head down to Cafe Augustine for craft coffee and house-made pastries.
Santana Row boasts some of the best shopping in the city, and the holidays are an extra-special time to visit. In addition to upscale 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!
Just across the street from Santana Row, the Westfield Valley Fair shopping mall transforms into a festive wonderland filled with sparkling lights, elegant decorations, and cheerful music. Shoppers can enjoy seasonal events, Santa visits, and exclusive holiday pop-up shops while exploring luxury boutiques and some of their favorite retailers. The warm, vibrant atmosphere makes it a perfect destination for holiday shopping, dining, and celebrations with family and friends.
Afternoon
Drop off your shopping bags in your room and grab your coat because it’s time to head downtown! Eos & Nyx offers an elegant brunch, where the menu shines with options like a smoked salmon Benedict, a mesquite grilled flat iron steak and eggs, chicken and waffles, and delicious brunch cocktail options. It’s the perfect spot for both a relaxed brunch and an intimate date setting.
After lunch, enjoy some wintry ice skating in sunny California. Downtown Ice is located in 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. Check the Winchester Mystery House events schedule to see what holiday festivities are happening in December.
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
Start 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, The Center for the Performing Arts, San Jose Civic, and Montgomery Theater. There are plenty of holiday performances at each venue, including Symphony San Jose's Holiday Spectacular and the San Jose Nutcracker!
Evening
After the performance, enjoy a short walk 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, order a ride to the intersection of Cherry and Glen Eyrie Avenue in San Jose's Willow Glen neighborhood to experience a festive, community-oriented holiday experience. Wander through the streets of Christmas lights, walk past enormous reindeer that tower over the neighborhood homes, and sip hot cocoa as you take in all the Christmas magic. Or, if you prefer not to walk, you can make a reservation through San Jose Brew Bike and experience a Willow Glen Holiday Light Tour! The 60-minute pedal bike tours run from 12/3 - 12/23.
