50 Perfect Hours: Gilroy and Watsonville

Drive 90 minutes south of San Francisco on US-101 and you will soon hit the 50,000-person cities of Gilroy and Watsonville, both known as thriving agriculture centers—Gilroy is referred to as the “garlic capital” and hosts the Gilroy Garlic Festival at the end of July every year.

Both locations offer tasty restaurants and tons of activity options. Here, we detail the perfect way to spend a 50-hour getaway in Gilroy and Watsonville.

Day 1

7:30 a.m. – Wake up in your spacious (750-square-foot) bungalow at Rosewood CordeValle, a luxury property located just minutes from Gilroy in the town of St. Martin. Throw on your robe, turn on your fireplace and open the doors to your terrace. Then, order some room service and eat a leisurely breakfast.

9:00 a.m. – When you are ready, dress in golfing attire and head out for some on-property golf on the hotel’s sprawling 260-acre course (advance reservations required).

1:30 p.m. – Once you are finished, change into some causal clothes and point your GPS to 946 Main Street in Watsonville. About 30 minutes later, settle into a table at Cowboys Corner Café, a popular local spot. The portions are large here—perfect if you are famished. This place is known for its breakfast, so why not have two in one day? Opt for the banana pancakes and chicken fried steak.

2:30 p.m. – Full and happy, drive three miles up the road to 150 Aviation Way. Here, you will have the option to choose from a variety of air tours with Specialized Aviation. Consider booking a biplane ride or a helicopter tour of the coast. Call in advance to make your reservation and enjoy seeing California from a bird’s-eye view.

3:30 p.m. – Drive a mile south to Rudon-Smith Winery, a beautiful spot that offers public tastings between 12 p.m. and 5 p.m. on Saturday and by appointment. Check out the wall murals while sipping some delicious Pinot Noir and Syrah.

5:30 p.m. – Ready for some dinner, drive eight minutes into downtown Watsonville and grab a chair at Jalisco Restaurant, one of the best Mexican eateries in the area. Start with a serving of ceviche and then move on to the Chile Verde and Chimichanga dinner before heading back to Rosewood CordeValle and turning in for the night.

Day 2

9:00 a.m. – Wake up a little later this morning and get ready to enjoy a day in Gilroy. Drive six miles south, park near 7400 Monterey Road and walk into Old City Hall Restaurant, the perfect place for breakfast. Opt for the Denver omelet, breakfast croissant and the pancake combo. Wash it down with a cup or two of steaming coffee.

10:30 a.m. – You are already in the center of downtown, so keep your car parked and go out on foot to explore the cute shops along Monterey Road, including Amoretto Boutique, Gilroy Antiques and The Nimble Thimble.

12:30 p.m. – Bop into Garlic City Café for lunch and dive into a Cajun chicken salad, penne pasta with prawns Florentine or calamari steak sandwich.

1:30 p.m. – The Gilroy/Watsonville area is known for is excellent wine—now it is time for some winery hopping! First stop: Solis Winery, an award-winning spot in the Santa Clara Valley that is open almost every day between 12 p.m. and 5 p.m. Once you’ve tried a few wines there, head over to Fortino Winery, just a few minutes down the street, to sip other varietals.

4:30 p.m. – On your way back to the hotel, consider stopping at the Gilroy Premium Outlets, a well-laid-out shopping center that features stores ranging from Coach and Carter’s to Kate Spade and Lacoste.

5:30 p.m. – Time for some rest and relaxation. Now back at the hotel, walk over to the on-site Sense Spa and spend the next hour (better yet, 90 minutes) enjoying a facial, wrap or massage.

8:00 p.m. – Feeling fabulous, change into some nice dinner clothes and walk to Il Vigneto, Rosewood’s 68-seat, private (only for resort guests and on-property golfers) Italian restaurant. Chat with your server about specials for the night and then consider the grilled monkfish, oak smoked beef short ribs and wild mushroom risotto.

Day 3

10:00 a.m. – Wake up slowly this morning, check out of the resort and drive 10 minutes south to the Gilroy Donut House from some morning treats (the cinnamon twists are to die for). From there, run into Garlic World, a specialty store for all your garlic needs. Grab some double garlic olive oil and smoked flavored olives (great gifts for your family back home), and then point your car toward the airport. This is the perfect way to end a 50-hour getaway in Gilroy and Watsonville.


Katie Morell is an independent journalist based in San Francisco who writes about travel, business and social justice issues. Her work has appeared in Hemispheres, Fast Company, USA Today, Diversity Woman, BBC Travel and others. Read more of her work at www.katiemorell.com