Last Updated on January 21, 2024

As enticing as the cable cars and cioppino of San Francisco can be, California’s Bay Area is stacked with other options for travelers seeking more rural or small-town adventures.

On an excursion south from the city along the bayside of the San Francisco Peninsula, I explored several not-to-be-missed sights. At the serene country estate of Filoli, I enjoyed a wine tasting hosted by the prestigious San Francisco Wine School. Dinner followed in the walkable town of Burlingame at an inventive plant-based restaurant started by a Silicon Valley engineer.

My day trip to the peninsula was part of a West Coast Wine cruise aboard the Discovery Princess. The cruise began in Vancouver, B.C., and included an overnight stay in San Francisco.

A Golden Welcome to San Francisco

The water in San Francisco Bay shimmered in the midday sun on a gloriously cloudless fall day as the Discovery Princess glided under the Golden Gate Bridge. Alcatraz, the infamous island prison, loomed in the distance as the city’s celebrated seven hills seemed to envelop us as the ship docked at Pier 27 along the Embarcadero.

From the terminal, I joined a group of travelers on a chartered bus for the beautiful 30-mile drive south along the rugged slopes of California’s Santa Cruz Mountains.

The San Francisco Peninsula, which stretches from San Francisco to San Jose in the south, is justifiably recognized for its stunning scenery. The Pacific side boasts 60 miles of beaches. Nearly 100 parks and two dozen Michelin-starred restaurants reside in the charming towns and cities on both sides of the peninsula. 

Filoli: A Hidden Bayside Treasure

Blazing Gingko and the Sunken Garden.
Blazing Gingko and the Sunken Garden. Photo by Liberte Reilly

As San Francisco’s high-rise towers faded, the terrain turned hillier and more pastoral. Our driver initially missed the entrance to Filoli Historic House & Garden. The massive, ivy-draped brick mansion is well hidden from the road, one of the reasons U.S. President Joe Biden hosted a historic meeting with Chinese President Xi Jinping here in late 2023.

Privacy is exactly what the original owners had in mind when they purchased more than 650 acres in 1915 in what is now Woodside. The long, twisty drive to the house passes fields, orchards and towering oak trees.

Considered one of the finest country estates of the 20th century, Filoli was built by San Francisco power broker William Bowers Bourn III, whose companies mined gold and supplied water to the Bay Area.

Filoli Mansion Now a Museum

Wealthy, well-connected Bay Area residents gathered for decades in the 54,000-square-foot Georgian revival-style mansion with 10 bedrooms and 15 bathrooms. The historic house became a museum when the family ceded the estate to the National Trust for Historic Preservation in 1975.

What distinguishes the estate are its gardens, a masterpiece of landscape design. About 16 acres of English Renaissance-style gardens buffer the mansion with massive plantings of roses and other flowers interspersed with bubbling fountains and artsy statuary.

A Gentleman’s Orchard of apple, pear, peach, and other fruit trees covers 16 acres. Miles of walking trails wind through the hilly, forested estate. Unsurprisingly, the BBC named Filoli one of the top 10 gardens worth visiting in North America.

Gardens Delight with Color

Fioli formal gardens.
Filoli formal gardens. Photo by Barbara Redding

On my stroll around the estate, I was enchanted by the still-flowering pastel roses and the bright orange color of the fall-blooming aloe plants framing the sunken garden. 

On a sunny patio, Master Sommelier David Glancy dispelled traditional views on pairing wines based on food color at a tasting hosted by his prestigious San Francisco Wine School.

“There are no rules,” Glancy said.

He should know; he’s one of only a dozen people credentialed as a master sommelier and a certified wine educator.

Glancy usually trains professionals and consumers with a passion for wine at the school in South San Francisco. He advised my group to challenge conventional wine pairings as we sampled several California and European reds and whites served with cheeses and pickled vegetables.

Burlingame Eucalyptus Trees

All too soon, we were back on the bus headed south to Burlingame, a city of about 30,000 people known for its tall eucalyptus trees and strollable streets. 

Bob Trahan greeted us in the spacious courtyard of Twelvemonth, the plant-based restaurant he founded in 2023. The former director of engineering at Meta (parent company of Facebook) in nearby Menlo Park, traded high-tech stress for culinary school.

Casually dressed in shorts, a T-shirt, and a baseball cap, Trahan recounted his ‘pivot’ to restaurant ownership, which he described as a quest to, “help people eat less meat and live sustainably.” 

Vegan Restaurant Goes High-Class

The bar at Twelvemonth.
The bar at Twelvemonth. Photo by Barbara Redding

Twelvemonth is the impressive result of his journey. Trahan converted a utilitarian brewery shuttered by the Covid-19 pandemic into a classy space with high-end décor. The chef-owner said he is swinging for a Michelin star with a menu of innovative plant-based dishes and creative cocktails designed to appeal to vegans and “non.” 

The restaurant’s casual courtyard is popular for lunch and happy hour. High ceilings, huge windows and leafy green plants welcome guests inside to a modern bar and an airy dining room. 

I was immediately taken with the starters, which included still-warm Twelvemonth rolls made with Furikake, a Japanese substitute for butter. Crisp, fried maitake mushrooms with ranch dipping sauce substituted for calamari and were quickly devoured by my tablemates.

A Creative Vegan Take on Traditional Dishes

Entrée items ranged from meatless pasta dishes like companelle with Cajun-spiced vegetables and tamales with smoked oyster mushrooms. There is no meat or seafood in Not Paella, but it’s packed with a medley of delicious seasonal vegetables.

The drink menu contains equally adventurous cocktails and mocktails. I chose a tart drink called Pear Pressure with cucumber-infused gin and Williams pear brandy. The Herbivore on the mocktail list is infused with green tea and celery soda. 

It is entirely possible to fill up on vegetables here.

Instead of dessert, we explored downtown Burlingame’s lively restaurant and bar scene.

Room for Gelato

The gelato offerings at Caffe Stellato proved too tempting, however. I indulged in a scoop of pistachio. At Copenhagen Bakery & Café, I chose a chocolate chip cookie for a snack on the ship.

As the bus returned to the big-city lights, I was pleased that my day on the bayside of the San Francisco Peninsula delivered more than just a change of scenery. 


  • Barbara Redding

    Barbara Redding is a freelance travel writer based in Austin, Texas, A retired journalist, she loves to explore new destinations as well as revisit familiar places. She’s written about luxury resorts in Bali, a Hindu wedding in India, snorkeling in Cuba’s Bay of Pigs, and saving sea turtles in Jamaica.