A message from the author, Frank Johnson, executive director of Visit Gilroy.
Gilroy has long been a travel hub for vacationers and California road trippers. In April of 2025, I had three friends and fellow Air Force veterans visit me from Kansas and Pennsylvania. As they haven’t seen much of California, my travel companions requested a mix of iconic, must-see experiences and off-the-beaten-path things to do. CHALLENGE ACCEPTED. Yes, I am the executive director of Visit Gilroy, but I genuinely feel this is one of the most amazing road trips in the country, and I’m very pleased to share it with other travelers.
I hope you like what we dubbed “The Bay Area-Garlic Town Loop!” - Frank Johnson
Days 1-2: San Francisco's Iconic Allure
Our adventure began in San Francisco, the perfect launching point with its international airport. We headed straight for the Golden Gate Bridge. Driving across this engineering marvel never gets old! We stopped for lunch in charming Sausalito at Taste of Rome, where the gnocchi gorgonzola was very tasty.
Travel Tip: When in San Francisco, it’s a good plan to get any driving out of the way first, park your car near your hotel, and use the many rideshare or public transportation options.
Back in the city, we navigated the famous crooked section of Lombard Street before checking into Hotel Spero. That evening, we walked to Chinatown and discovered the restaurant Bow Hon, where the food was certainly elevated over your typical Chinese restaurant in most towns. We capped off our night at Cityscape Sky Bar, with incredible 360-degree views of the magnificent San Francisco skyline.
Day two brought us to Alcatraz Island, where an ominous gloom pervades the notorious prison. Afterward, we explored Fisherman's Wharf and indulged in San Francisco's signature dish, cioppino, at the aptly named Cioppino's. This dish is a fisherman’s strew in a tomato sauce invented by early Italian residents. A cable car ride back to our hotel was a “must do” option for those working on their bucket list.
Days 3-5: Coastal Magic Down HWY1 to Santa Cruz & Monterey
On Tuesday, we kicked off our coastal adventure by driving down the legendary Highway 1, aka the Pacific Coast Highway, with dramatic cliffs and many vantage points to pull over and explore. We fueled up with breakfast at The Breakers at Rockaway Beach -- a pleasant location worthy of a night stay! The relaxing drive continued to the Dream Inn in Santa Cruz, where our rooms direct overlooked the beach.
Next, the Santa Cruz Beach Boardwalk offered nostalgic amusement park fun with plenty of sweets, treats, corndogs and people watching. We headed over to the pier to watch the sea lion shenanigans and enjoy drinks at Olitas Cantina while chatting with their friendly bartenders.
Travel Tip: The Sky Glider tram ride over the Santa Cruz Boardwalk is an excellent, peaceful way to take in the coastal views.
The following morning, we grabbed breakfast burritos with chorizo, cheese and potatoes from the Point Market and watched surfers ply the waves at Pleasure Point. Close by, the redwood forest of Nisene Marks State Park was too tempting to pass up. A short but stunning hike through the primeval canopy of trees had us searching for the region's famous banana slugs before we continued the picturesque drive to Monterey, stopping at some fruit stands along the way. The day ended at Asilomar State Beach in Monterey with the simple pleasures of crashing waves, seasonal flowers and an ocean breeze. We connected cool sand with our tired toes and relaxed.
Day five brought another bucket-list experience: whale watching with Chris's Fishing and Whale Watching. We spotted dozens of whales and hundreds of dolphins and porpoises to the cheers of those on the boat. Fortune smiled upon us with a rare sighting of Northern right whale dolphins! The boat had several guests from outside the U.S. saying this was their best day ever, and it was a reminder not to take what we have for granted.
Travel Tip: Whale watching is seasonal, so do your research!
Back on land, a bread bowl filled with clam chowder from Abalonetti Bar & Grill warmed us up. Wine tasting at A Taste of Monterey offered magnificent views of playful sea otters, and a stroll down historic Cannery Row completed our Monterey experience.
Days 6-7: Inland Treasures from Watsonville to Gilroy
Bidding farewell to the ocean, we headed inland to Watsonville. The name “Martinelli’s” may ring a bell. They are known for their sparkling cider and single-serving, apple-shaped bottes of delicious cider. Tasting at the factory provided a refreshing break, and we followed it up with another local gem: olallieberry pie at Gizdich Farms. The tart, fruity goodness and flaky crust begs for some vanilla ice cream, and hey, you deserve it!
Next it was on to Highway 152 and its scenic drive with a stop at Mt. Madonna County Park and the amazing redwood forest, only 15 miles from Gilroy. The forest aroma and canopy of cooling trees are worth the stop! Then it was time for some history and culture at the Chitactac-Adams Native American Cultural site, with a profound connection to the area's indigenous history in a place that's been a significant meeting spot for thousands of years.
Travel Tip: No Gilroy visit is complete without stopping at Garlic World. Visitors must try the garlic chocolate chip cookies and garlic ice cream! Garlic World is also home to the world's largest garlic braid.
Next stop: wine country. The Santa Clara Valley region around Gilroy offers award-winning wines and friendly winemakers. The Wine Trolly dropped us off in beautiful downtown Morgan Hill where we explored a bit and grabbed some appetizers. Family-run operations like Solis Winery and Satori Vineyards, exemplify the authentic, passionate approach that makes this area special. Our group had time for two winery stops, but there are more than 30 wonderful vintners on the Santa Clara Valley Wine Trail.
We ate well on this trip, but the Mexican food in Gilroy was a true highlight. With 30 Mexican restaurants on the "Taco Trail," we had to try Tacos Ameca #2, where the al pastor tacos and carnitas were exceptional. We also made time for a jaunt through historic downtown Gilroy, with its taprooms, Gilroy Bowl, art galleries and cultural hot spots to explore.
On our second Gilroy day, we hopped aboard the Morgan Hill Wine Trolley, touring Besson Family Vineyards, Tuscan House and Kirigin Cellars, allowing us to sample liberally without worrying about driving. Dinner at Old City Hall in Gilroy fascinated us with its preserved jail cells and bank vaults – a meal with a side of history!
Days 8-: Cultural Gems & Homeward Bound
Our final leg began with antique shopping at The Barn at Hoey Ranch and family fun at Gilroy Gardens, where we tried the surprisingly delicious Garlic Funnel Cake. The historic Mission at San Juan Bautista, built in 1797, offered that quintessential California experience, and by lucky timing, we stumbled upon a rib cook-off complete with mouthwatering barbecue and live music.
As our loop neared completion, we made final stops at San Jose's Winchester Mystery House and enjoyed lunch at Santana Row before heading back to the San Francisco Airport.
Travel Tip: While San Francisco International is the largest airport in the region, San Jose International and Oakland International are also good options depending on your itinerary and flight prices.
This eight-day journey perfectly balanced iconic destinations with hidden treasures. From the majesty of the Golden Gate Bridge to the quirky delight of garlic ice cream, the Bay Area-Garlic Town Loop delivered exactly what makes a road trip memorable: unexpected discoveries amid California's natural beauty.
