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San Francisco and Napa Valley Winter Weekend Itinerary January 23-25 2026

Viewed by 59 travelers
Day 1 · Fri, Jan 23
San Francisco

Arrival and Comedy at SF Sketchfest

Morning:

As you arrive in the city via San Francisco International Airport (SFO) this afternoon, head straight to your hotel near Union Square to drop your bags and freshen up. Take a short walk through the nearby Maiden Lane to admire the high-end boutique storefronts and get your first taste of the vibrant San Francisco energy before the festival begins.

Afternoon:

Continue your late afternoon with a scenic stroll along the Embarcadero, enjoying the refreshing bay breeze and the iconic sight of the Bay Bridge. Stop by the [Ferry Building Marketplace](https://www.ferrybuildingmarketplace.com) to browse local artisan shops and grab a quick pick-me-up from [Blue Bottle Coffee](https://www.google.com/search?q=Blue+Bottle+Coffee+official+site) before the night's comedy events begin.

Evening:

Kick off your night with a flavorful dinner at [Absinthe Brasserie & Bar](https://www.google.com/search?q=Absinthe+Brasserie+%26+Bar+official+site) in the charming Hayes Valley district. Afterward, experience the highlight of the winter season at SF Sketchfest with a live comedy performance at the iconic Sydney Goldstein Theater. End your first night on a high note by sipping a creative cocktail at the nearby [Smuggler's Cove](https://www.smugglerscovesf.com/menu).

Day 2 · Sat, Jan 24
San Francisco

Arts, Design, and the SF Symphony

Morning:

Begin your morning with a specialty pastry and coffee at the industrial-chic [Tartine Manufactory](https://www.tartinebakery.com/san-francisco/manufactory) in the vibrant Mission District. Afterward, delve into the city's artistic soul at the [SFMOMA](https://www.google.com/search?q=SFMOMA+official+site), where you can browse the Fisher Collection and admire the massive green Living Wall on the third-floor terrace.

Afternoon:

Explore the cutting-edge residential and commercial art galleries at the [Minnesota Street Project](https://minnesotastreetproject.com) situated in the trendy Dogpatch neighborhood. Afterward, transition toward the performing arts hub by browsing the upscale boutiques of Hayes Valley, making sure to visit [Reliquary](https://reliquarysf.com) for unique vintage finds and grabbing a craft sourdough snack at [Josey Baker Bread](https://www.joseybakerbread.com).

Evening:

Savor a sophisticated pre-theater dinner at the modern French bistro Monsieur Benjamin before walking to the iconic Davies Symphony Hall for a world-class performance by the San Francisco Symphony. Wrap up your cultural deep-dive with a masterfully crafted cocktail among the library stacks at [The Interval at Long Now](https://theinterval.org/menu), enjoying an atmosphere that perfectly mirrors the day's artistic theme.

Day 3 · Sun, Jan 25
Napa Valley

Napa Valley Restaurant Month and Lighted Art Festival

Morning:

Bid farewell to the city as you drive across the iconic Golden Gate Bridge toward the rolling vineyards of wine country for the final leg of your journey. Upon arriving in downtown Napa, head to the bustling [Oxbow Public Market](https://oxbowpublicmarket.com) to grab a legendary, griddle-fried English muffin from the [Model Bakery](https://www.themodelbakery.com) for a perfect morning treat. Enjoy your breakfast while strolling along the scenic Napa Riverfront, taking in the crisp winter air and serene water views before your afternoon of tastings begins.

Afternoon:

Spend your afternoon immersed in the downtown creative scene by exploring the vibrant, large-scale sculptures and immersive installations of the [Napa Lighted Art Festival](https://donapa.com/event/napa-lighted-art-festival) positioned throughout the city's parks. Afterward, take advantage of Napa Valley Restaurant Month by enjoying a curated wine flight and artisan bites at the chic [Alpha Omega Collective](https://www.alphaomegacollective.com/tours-tastings/napa) tasting room.

Evening:

As the sun sets, indulge in a celebratory multi-course dinner at [TORC](https://www.google.com/search?q=TORC+official+site), where the seasonal Napa Valley Restaurant Month menus showcase local farm-to-table excellence. Cap off your weekend by wandering through the mesmerizing glowing projections at [First Street Napa](https://firststreetnapa.com) before enjoying a nightcap with panoramic views of the valley at [Sky & Vine Rooftop Bar](https://www.skyandvine.com/menus).

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