San Francisco and California’s Wine Country offer an unforgettable blend of rich history, natural beauty, and vibrant culture. This “Double Take” explores two perspectives on the region: one immersed in the urban charm and iconic landmarks of San Francisco, and the other basking in the rolling vineyards and laid-back elegance of Napa and Sonoma.
San Francisco, once the epicenter of the Gold Rush and a cultural crossroads during the counterculture movement of the 1960s, still hums with a unique energy. From its historic cable cars and the Victorian-lined streets of Alamo Square to the haunting tales of Alcatraz and the sweeping views from the Golden Gate Bridge, the city invites both first-time visitors and seasoned travelers to explore its layers.
Just an hour or two north, Wine Country opens up a completely different experience. Napa Valley and Sonoma County, rooted in centuries of agricultural heritage and winemaking traditions dating back to the 1800s, offer a slower pace and a celebration of the senses. With world-class wineries, farm-to-table cuisine, and charming towns like Yountville and Healdsburg, this region invites visitors to unwind among the vines, savor award-winning vintages, and enjoy scenic drives through sun-dappled hills.
Whether you’re craving the buzz of a world-class city or the serenity of wine country, this guide shares how each place shines in its own right—and how returning with fresh eyes can make the experience even richer.
The Same
Before kids, The Family explored Northern California so both the “Dinks and the Faily were kid-free trips. San Francisco dazzled with its legendary landmarks and vibrant neighborhoods, while Napa and Sonoma delivered unforgettable sips among stunning vineyard views. We crossed the Golden Gate Bridge on foot, rode historic cable cars, heard the echoes of Alcatraz, and followed the sea lions’ barking call to Pier 39. Later, we traded city bustle for vineyard elegance—tasting at Robert Mondavi, riding the tram to Sterling Vineyards, and stepping back in time at Sonoma’s Buena Vista Winery. Whether as a couple or a soon-to-be family, the experiences were rich, flavorful, and distinctly Californian.
San Franciso
San Francisco, fondly nicknamed “The City by the Bay,” is a vibrant Northern Californian city brimming with iconic landmarks, historical sites, cultural experiences, and outdoor adventures.
Golden Gate Bridge:
Undoubtedly the crown jewel of San Francisco, the Golden Gate Bridge is a majestic suspension bridge that has become a global symbol of the city. Take a walk or bike across the bridge for breathtaking views of the city skyline and bay or explore its history at the visitor center. We chose to walk and it was quit the journey.
Ride a Cable Car
Riding a cable car in San Francisco is a must-do experience and a fun way to conquer the city’s steep hills. We hopped on and held tight as we clanged through neighborhoods, soaking in views of historic buildings, bay breezes, and that nostalgic, bell-ringing charm unique to the City by the Bay.
Alcatraz Island:
This former prison perched on a rocky island offers a glimpse into a notorious past. Take a ferry to the island and tour the foreboding cell house, listen to stories of former inmates, and enjoy chilling Alcatraz sights and sounds.
Fisherman’s Wharf & Pieer 39:
This lively waterfront district is a must-visit for tourists. Enjoy fresh seafood at pier 39, take a scenic cruise on the bay, visit Ripley’s Believe It or Not museum, or witness the barking sea lions at Pier 39. I was worried we didn’t know exactly where the sea lions would be located but you just need to follow the sounds of their bark.
Lombard Street
Lombard Street, famously dubbed “the crookedest street in the world,” is a quirky San Francisco landmark with eight sharp hairpin turns framed by beautifully manicured gardens. Whether you’re driving down or strolling alongside, it’s a fun and photo-worthy stop that perfectly captures the city’s charm and eccentricity.
Chinatown: Immerse yourself in the sights, sounds, and smells of San Francisco’s vibrant Chinatown, one of the oldest and largest Chinatowns outside of Asia. Explore bustling shops and restaurants, ornate temples, and experience a unique cultural atmosphere.
Napa ValleY
Napa Valley is one of the world’s premier wine regions, celebrated for its picturesque vineyards, award-winning wines, and sophisticated yet welcoming atmosphere.This sun-soaked valley is home to over 400 wineries ranging from historic estates to innovative newcomers. Napa is especially renowned for its Cabernet Sauvignon and Chardonnay, and offers unforgettable experiences like wine tastings, vineyard tours, hot air balloon rides, and farm-to-table dining.
Robert Mondavi Winery:
One of my favorite stops in Napa was the Robert Mondavi Winery. It’s the perfect place to grab a glass of world-class wine and soak in the sunshine with views of the gorgeous To Kalon Vineyard. Known for their signature Fumé Blanc and exceptional Cabernet Sauvignon, this spot blends great wine, art, and culture in the most relaxing and beautiful way.
Sterling Vineyards:
Sterling Vineyards was one of the most unique wine experiences I’ve had. The moment I stepped onto the aerial gondola and started the ride up to the winery, I knew this was something special. Floating above the valley with stunning panoramic views all around was absolutely breathtaking. Once at the top, the Mediterranean-style buildings and peaceful setting made me feel like I’d stumbled into a hidden hillside retreat. I grabbed a glass, found a cozy spot to sit, and just soaked in the beauty of the valley below. It was the perfect place to unwind and sip some truly delicious wine.
Beringer Vineyards:
Beringer Vineyards in St. Helena was a highlight of our Napa trip. As the oldest continuously operating winery in Napa Valley, established in 1876, it offers a rich blend of history and elegance. We wandered through the beautiful gardens and admired the stunning Rhine House, a 19th-century Victorian mansion adorned with intricate woodwork and stained glass windows. The tasting experience was exceptional, featuring their renowned Chardonnays and Cabernets. Sipping wine on the veranda, surrounded by the estate’s timeless charm, made for an unforgettable afternoon.
Chateau Montelena:
Chateau Montelena, established in 1882, is a historic Napa Valley winery renowned for its 1973 Chardonnay that won the 1976 Judgment of Paris. The winery is set in a charming ivy-covered stone castle, nestled at the base of Mount Saint Helena. Its serene grounds, complete with a picturesque lake and lush gardens, provide a peaceful setting for wine tasting. Guests can explore the winery’s rich history and enjoy a variety of curated wines, making it a memorable stop for both wine enthusiasts and those seeking a tranquil, beautiful experience in Napa.
Sonoma
Sonoma feels like a charming escape, offering a more laid-back vibe compared to Napa. With its small-town atmosphere, rolling vineyards, and historic plazas, Sonoma has a way of making you feel at home. Whether you’re enjoying a quiet afternoon at a local winery or strolling through its quaint streets, it’s the perfect place to unwind and savor the essence of California wine country.
Buena Vista Winery:
Buena Vista Winery, established in 1857 by Hungarian Count Agoston Haraszthy, is California’s first premium winery and one of its oldest continuously operating establishments. Located just east of Sonoma, the winery is recognized as a California Historical Landmark and is listed on the National Register of Historic Places . The estate features historic wine caves, a reconstructed Palladian villa, and offers a range of exceptional experiences tailored to any occasion . Today, Buena Vista Winery continues to produce award-winning wines, including Pinot Noir, Chardonnay, and Cabernet Sauvignon, under the ownership of the Boisset Collection .
Gundlach Bundschu Winery:
Gundlach Bundschu Winery, nestled in Sonoma Valley, is California’s oldest continuously family-owned winery, established in 1858. The estate spans 320 acres at the crossroads of Sonoma Valley, Carneros, and Napa Valley, and is renowned for its regenerative organic farming practices. Under the guidance of sixth-generation vintner Jeff Bundschu, the winery produces small-lot, estate-grown wines, including Cabernet Sauvignon, Merlot, Chardonnay, and Gewürztraminer
Jacuzzi Family Vineyards:
Established in 2007 by Fred Cline to honor his grandfather Valeriano Jacuzzi, the winery features a Tuscan-style estate inspired by the family’s ancestral home in Italy. Visitors can enjoy a variety of Italian varietals, including Pinot Grigio, Barbera, and Teroldego, in a setting that evokes the charm of the Italian countryside. The winery also houses The Olive Press, offering olive oil tastings and a selection of gourmet products.
Sebastiani Vineyards:
Sebastiani Vineyards & Winery, located in the heart of Sonoma, offers a rich blend of history and contemporary winemaking. Established in 1904 by Samuele Sebastiani, an Italian immigrant, the winery is situated on land originally planted with vines in 1825 by the Mission San Francisco Solano. This makes it one of the oldest wineries in California. Today, the winery is known for its Cherryblock Vineyard, planted in 1961, which continues to produce acclaimed Cabernet Sauvignon .
Local Cuisine
- Ghirardelli Square: Indulge in chocolate treats and explore boutique shops in this historic confectionery complex.
- Clam Chowder in a Sourdough Bowl: A San Francisco classic, this creamy, flavorful clam chowder is served inside a freshly baked sourdough bread bowl, offering the perfect combination of comfort and tang.
- Dungeness Crab: This sweet, succulent crab is a local delicacy, often served steamed or in crab cakes, reflecting the city’s rich seafood culture.
- Mission-Style Burrito: Originating in the Mission District, this oversized burrito is filled with rice, beans, meat, and a variety of toppings, wrapped in a large flour tortilla—a perfect meal for on-the-go.
- Dim Sum: With a strong Asian influence in San Francisco, dim sum is a popular choice, offering a variety of steamed, fried, and baked small dishes typically enjoyed with tea.
- Sourdough Bread: San Francisco’s famous tangy sourdough bread is a result of the city’s unique natural yeast culture, best enjoyed as a side or in the iconic sourdough bowl.
The DINKs
San Francisco
In addition to soaking up the attractions above in San Franciso and sipping our way through wine country, we also made sure to take in a bit of San Francisco’s iconic culture. We caught a game, because no trip is complete without a little sports action and wandered through the colorful, eclectic streets of Haight-Ashbury. It was the perfect blend of laid-back vineyard vibes and city energy.
Haight-Ashbury: Take a trip back in time and explore the legacy of the 1960s counterculture in the Haight-Ashbury district. Browse vintage clothing stores, listen to street performers, and soak in the district’s hippie vibes.
Catch a Game in San Francisco: San Francisco boasts a passionate sports scene with several teams playing within San Francisco and the surrounding areas. Both growing up 49ers Fans, The Dinks chose this opportunity to see them live at Levi’s Stadium, located in Santa Clara, California.
Summary
California’s Wine Country is a dream destination for wine lovers, foodies, and nature enthusiasts alike. Stretching across Napa, Sonoma, Mendocino, and neighboring counties, the region is home to more than 1,700 wineries, each offering a unique take on California’s rich viticultural heritage. From historic estates like Buena Vista and Beringer to modern, sustainable vineyards like Cline Cellars, Wine Country blends old-world charm with innovative winemaking. Beyond the vineyards, visitors can enjoy gourmet dining, scenic hikes, hot air balloon rides, and luxurious accommodations. Whether you’re sipping a bold Cab in Napa or enjoying a crisp Chardonnay in Sonoma, Wine Country offers a perfect blend of flavor, beauty, and relaxation.
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