Second Date Ideas in San Jose

Sit down for a guided tasting at J. Lohr San Jose Wine Center just south of downtown, where the historic urban tasting room has seating indoors and outside. The seated flights feature small-lot wines or bottles sold only at the winery, and you can often add a cheese or charcuterie board. A limited private lot is on site, with more street parking along Lenzen Avenue.

Cook several courses together at Taste Buds Kitchen in south San Jose near Almaden Valley. The hands-on Adult Cooking Classes & Date Nights are for ages 18 and up, with events running seven days a week and some sessions offered as BYOB. Check the class calendar for dates.

Explore the Winchester Mystery House together, a 160-room mansion in west San Jose where doors open onto walls and staircases climb into ceilings. The 65-minute Mansion Tour passes through 110 rooms and includes garden access. You can also choose an evening flashlight tour, while October brings Halloween Haunt decorations throughout the house.

Make a night of the opera at the California Theatre downtown, a 1927 former 1,122-seat movie palace with ornate plasterwork and chandeliers preserved through its restoration. Opera San José presents four mainstage productions here each year. The 2026-27 season includes Fiddler on the Roof from November 15 through 29, Doctor Atomic from February 14 through 28, 2027, and Carmen from April 18 through May 2, 2027.

Spend the afternoon at Burke Williams Day Spa on Santana Row, where Morocco-inspired interiors use deep earth tones, hand-rubbed walls, arches and carpets, with marble and granite in the spa areas and a fireplace in the lounge. Shops along Santana Row are close by for a wander afterward.

Spend some time together at the San Jose Museum of Art downtown, where exhibitions of modern and contemporary art are shown alongside the museum's own collection.

Start with dinner at The Pressroom in downtown San Jose, where the 1884 Lyndon Building now holds a 160-seat dining room with floor-to-ceiling windows, greenery between tables, cognac leather seating and a central bar. Afterward, move next door to Bar Mercury, reached through its own entrance or the dining room, for a cocktail in a darker mid-century room with hexagonal booths and a back lounge.

Luna Mexican Kitchen on The Alameda is a lively cantina, with a full-service bar and a patio open to the air. The menu includes Baja-style fish tacos and sizzling parrilladas, with tortillas handmade from nixtamal corn, while the drink list covers margaritas and crafted cocktails.

For a more formal second date, La Foret serves classic French fine dining in a historic mid-19th-century building in the creekside Almaden Valley hills. The menu includes quail and poached lobster alongside an extensive wine list. The creekside setting is romantic, and the restaurant is known as a special-occasion spot.

Time dinner around sunset at The GrandView, a historic mountainside restaurant in the East San Jose foothills where patio tables look over the valley into the evening. The classic American menu includes beef, veal and seafood, while the farm-to-fork side draws from GrandView Farms for handcrafted pastas, steak, seafood and house-cured salami. For a longer meal, add wine pairings to the five-course tasting menu if you like.