Ease into the trip with breakfast at Mama's on Washington Square, savoring their famous omelettes and freshly baked pastries while watching locals stroll the North Beach streets. Afterward, take a gentle walk through Washington Square Park toward Coit Tower-ride the elevator up for sweeping views of the bay, then wander down to explore the colorful murals and cafés of nearby Telegraph Hill before a relaxed late-morning coffee at a neighborhood roastery.
Stroll south toward the waterfront and rent a bike near Pier 39 to ride the Embarcadero, pausing to watch the sea lions and grab an artisanal snack at Boudin Bakery (try the clam chowder in a sourdough bowl). Continue to Ferry Building Marketplace for a late-afternoon tasting of local cheeses and coffee at Blue Bottle Coffee, then relax on a bench by the bay as the light softens and plan an easy dinner in nearby Fisherman's Wharf or the historic Ghirardelli Square.
As twilight settles, wander through the atmospheric streets of North Beach to dinner at Tony's Pizza Napoletana for award-winning pies or choose the cozy Italian plates at Sotto Mare; afterwards, sip cocktails on the rooftop at El Techo for skyline and Bay Bridge views. Finish the night with a short walk to City Lights Bookstore for a late browse and people-watching over coffee at the nearby Cafe Trieste, keeping the pace gentle after a day of travel and sightseeing.
Start your morning with a hearty brunch at Zazie in Cole Valley, then stroll through the neighborhood to admire the painted Victorians on Alamo Square and snap photos of the iconic Painted Ladies against the skyline. From there, head to Haight-Ashbury to browse vintage shops and quirky boutiques, pause for a coffee at Reveille Coffee Co., and soak up the colorful counterculture history before making your way toward the waterfront for the afternoon.
Cycle or take a rideshare down to the waterfront to explore Fisherman's Wharf-watch the bay activity, sample fresh crab at a street stall, and visit the interactive exhibits at Madame Tussauds San Francisco for a bit of playful fun. From there, stroll west along the Embarcadero to the Ferry Building Marketplace to taste artisan chocolates at Recchiuti Confections and regional olive oils at Olivier & Co., then board a short historic ferry to Alcatraz Island for an early-evening audio tour that captures the island's dramatic history as the light begins to soften over the bay.
As twilight deepens, catch a cable car from the Powell turnaround and descend toward Union Square, then wander a few blocks to the atmospheric alleys of Chinatown for a family-style dinner at Z & Y Restaurant sampling Sichuan specialties. After dinner, head to the waterfront for a twilight stroll along Pier 7 to watch the lights of the Bay Bridge shimmer, and finish with inventive cocktails at The Riptide or a nightcap with live jazz at the intimate Black Cat to keep the evening lively but relaxed.
Begin with a coffee and pastry at Tartine Bakery before heading north to explore the sweeping views from the Baker Beach bluff-watch the morning light play on the Golden Gate Bridge and stroll the shoreline. Continue up the Presidio for a peaceful walk through the Lands End Lookout trails, pop into the Crissy Field promenade to watch windsurfers and grab a picnic from a nearby deli, then take time to visit the scenic Palace of Fine Arts lagoon for photos and a relaxed moment among the classical columns.
Head into the vibrant Richmond and Laurel districts for a late lunch at Burma Superstar (try the tea leaf salad) then wander the specialty shops and bakeries along Sacramento Street for a taste of local life. In the mid-afternoon, explore the serene gardens and museum galleries at The Legion of Honor, followed by a scenic drive or short hike up to Fort Point below the Golden Gate Bridge for dramatic close-up views and photography as the light shifts toward evening.
As the sun softens, make your way to the lively Crissy Field Center promenade for a gentle shoreline stroll with views of the bridge, then sidestep into the nearby Presidio Tunnel Tops green rooftop park for sunset picnicking and sweeping bay panoramas. After dusk, head to the charming Chestnut Street corridor in the Marina for dinner at A16 (coastal Italian and wood-fired specialties) followed by inventive cocktails at the cozy speakeasy The Interval at Long Now to round out the evening with conversation and curated drinks.
Head north from San Francisco for a scenic drive into Napa Valley and begin the day with a relaxed breakfast at Brix Restaurant & Gardens overlooking vineyard rows, followed by a stroll through their ornamental gardens to wake up your senses. After breakfast, enjoy a guided tasting at Domaine Carneros to sample sparkling wines and tour the elegant chateau, then visit the nearby Carneros Resort & Spa for a short walk among vineyard trails and a coffee before moving on to afternoon tastings.
After a sparkling morning, drive north to the iconic Stag's Leap Wine Cellars for a guided tasting of their renowned Cabernet Sauvignon and a walk through the historic vineyards, then continue to Artesa Vineyards & Winery to admire contemporary sculpture gardens and take in panoramic valley views from the hilltop terrace while sampling estate reds. Finish the afternoon with a relaxed pairing at O'Brien Estate Winery, where you can enjoy small-production wines alongside a curated cheese and charcuterie board on their sunny patio before returning to town as the light softens.
As twilight falls, unwind with a romantic stroll and sunset views at Downtown Napa's Oxbow Public Market-pick up small bites or a gourmet picnic to enjoy at the nearby riverfront park. For dinner, reserve a table at Cole's Chop House for classic steakhouse fare with a curated Napa-centric wine list, then finish the night with a nightcap at Cadet Wine & Beer Bar for relaxed local pours or a cozy, late-evening tasting of boutique wines.
Squeeze in a peaceful last morning with a light breakfast and bay views at The Plant Cafe Organic on Pier 3, then wander the nearby Embarcadero Center for quick souvenir finds and morning light over the water. Before you head to the airport, take a brisk stroll through the serene paths of Ina Coolbrith Park for one last skyline-and-bay perspective, and grab a coffee to-go from Ritual Coffee Roasters on your way out to keep the energy up for travel.
Spend a leisurely final afternoon wandering the leafy slopes of Russian Hill, popping into boutique shops along Polk Street and stopping for a late lunch at Tosca Cafe for classic San Francisco atmosphere. Afterward, take a scenic detour to Lombard Street to admire the famously winding block and then settle into the panoramic terrace at Ina Coolbrith-adjacent Ina Coolbrith Park's neighbor, Russian Hill Park, for last-minute photos before making your way to the airport.
For a relaxed final evening before departure, take a gentle stroll through Ghirardelli Square to pick up a chocolate souvenir and then settle at The Ramp for waterfront views and casual seafood plates as the sunset gilds the bay. Finish with a peaceful harbor-side drink at The Trident on the marina, where you can toast the trip while watching night lights ripple across the water and savor one last San Francisco panorama.