If you’re up for great cocktails with a lively vibe, 55 South in San Jose is a must-visit. Their menu combines classic drinks with unique ingredients, which keeps things exciting for cocktail enthusiasts. Whiskey fans will also love their extensive selection. On weekends, the DJ adds an energetic touch, making Fridays and Saturdays especially popular nights. If you want a seat, try to arrive early, as it can get busy during peak times!

MINIBOSS, a vibrant arcade bar in Downtown San Jose, combines craft cocktails, nostalgic 90s arcade games, and seasonal decor for an unforgettable night out. Sip unique drinks, savor delicious food, and immerse yourself in a lively atmosphere perfect for socializing. A must-visit spot for arcade lovers and holiday enthusiasts alike!

Nestled in a quaint San Jose neighborhood, Coterie Winery offers an intimate wine-tasting experience with exclusive wines sourced from small, renowned vineyards. Known for its warm wooden interiors and cozy atmosphere, it’s a perfect spot for dates or gatherings with friends and family. With beautifully presented glasses and tasting events that pair wine with food, Coterie provides a unique and inviting experience for wine lovers.

Discover Ancora Vino, a welcoming wine bar and shop in downtown San Jose’s South Bay. Known for fun monthly tastings and an affordable wine club, Ancora Vino’s events include mystery wine challenges led by Advanced Sommelier and co-founder Mike. With an extensive range of wines from luxury to budget-friendly, it’s ideal for any enthusiast. Enjoy curated wine and Italian food pairings with friends and family at this hidden gem, sharing space with Bibo’s Little Italy for pizza and Pour Decisions for craft beer.

Birre by Pour Decisions in downtown San Jose is a delightful beer garden offering a diverse selection of craft beers that will please any beer enthusiast. This family-friendly venue shares space with Bibo’s Little Italy for amazing pizzas and Ancora Vino for an impressive wine selection, making it ideal for gatherings with loved ones. Enjoy a vibrant atmosphere and a variety of options for both beer lovers and those seeking Italian cuisine, making it a perfect stop for any occasion.

20Twenty Cheese Bar offers a cozy, intimate spot perfect for gatherings with friends or romantic dates. Known for its excellent selection of wines and craft beers, it’s also a great place to enjoy a charcuterie board or a tasting platter with curated cheeses and meats, making it versatile whether you're in the mood for wine or beer. The bar's charming atmosphere and emphasis on quality pairings make it an ideal destination for a relaxing yet refined experience.