Gilroy is a relaxed, affordable South Bay base with rolling vineyards, the family-friendly Gilroy Gardens, a lively farmers’ market and famous garlic-forward food — great for multiple-week stays with nearby tasting rooms, outlet shopping and plenty of hiking and outdoor escapes.
It’s well connected by highways and regional rail, roughly 30 miles to San Jose, about 30–35 miles to Santa Cruz and ~45 miles to Monterey, so beaches, big-city dining and cultural outings are an easy weekend option.