On a recent weekend getaway, we biked around an oft-overlooked town at the base of Sierra Azules, drank wine in the Santa Cruz Mountains, and relaxed among the redwoods at a clothing optional resort.

Here is our guide to the best things to do in Los Gatos, some 60 miles south of San Francisco.

What to Do

Loma Prieta Winery1. Wine tasting is one of the region’s biggest draws. There are more than 70 wineries in the area, five of which can be enjoyed along the Los Gatos-Saratoga Wine Trail. Testarossa Winery is within an easy walk or 10-minute bike ride from downtown Los Gatos.

2. If you’ve opted for a traditional road trip, higher up in the Santa Cruz Mountains, the way to the wineries offers many photo opps of llamas and ocean vistas. If you have time to fit in just one place, go to Loma Prieta for delicious, generous pours and equally generous complimentary food pairings, plus some spectacular views off the romantic Mediterranean-style terrace. Dogs are welcome.

Vasona Park3. Rent bikes from Summit Bicycles. The 11-mile paved biking and jogging trail, Los Gatos Creek Trail, is two blocks away.

4. For two-wheeling picnickers, The Purple Onion is a beloved café with great sandwiches and salads. It’s also where the locals go for coffee, pastries or bottomless orange lemonade. Pick up lunch and cruise along the Los Gatos Creek Trail to Vasona Park, where there are numerous picnic pavilions and shaded scenic spots to choose from.

 

 

Where to Stay

Hotel Los Gatos1. With its Mediterranean villa feel, Hotel Los Gatos and Spa is itself worth the trip. Lounging out at the pool, or having room service deliver wine to your private balcony overlooking the terra cotta courtyard, you might decide to skip the area activities, lay low and luxuriate all weekend. The hotel has an on-site Greek restaurant, the Michelin-starred Dio Deka and on Friday evenings, the hotel and Testarossa Winery offer al fresco wine tastings.

2. A far-and-away different sleeping experience can be had at the clothing-optional Lupin Lodge, where accommodations include yurts, cabins, and camping. Promoting “social nudity” since 1936, Lupin Lodge has a swimming pool, tennis and volleyball courts, a sauna, hiking trails, and more. Guests can come for the day or stay overnight in this secluded resort in the redwoods.

Where (else) to Eat

Dio Deka1. The Michelin-starred Dio Deka at Hotel Los Gatos serves Hellenic cuisine and has an extensive wine list. It’s a no-brainer if you are staying at the hotel or celebrating anything—or just treating yourself to a high-end meal.

2. Nick’s on Main is a popular place for lunch and dinner. Lobster rolls, Kobe burgers and grilled strawberry desserts are some of the best items at this affordable American bistro.

Directions:
From San Francisco to Los Gatos, take Caltrain to the San Jose Diridon Station and transfer to the lightrail going towards Winchester Station. Take the lightrail 15 minutes to Winchester, which is the last stop, and hop on the #48 or #49 bus to Los Gatos. The bus comes once every hour, so check the VTA (Santa Clara Valley Transportation Authority) website for an exact schedule. Visit the Los Gatos Chamber of Commerce website for happenings around town.

Photo: Mary Wholey, Loma Prieta, madisonfall,  Hotel Los Gatos