Start the day with a leisurely coffee at La Colombe in Rittenhouse Square before heading to Philadelphia International Airport for your morning flight. Once you touch down at San Francisco International Airport, hop on the BART to Union Square, where you can check into your boutique hotel and unwind with a sunset view of the Bay.
After checking in, wander to the historic Ferry Building Marketplace for artisanal bites and wine tasting, then stroll along the Embarcadero to soak in bay views. Conclude the afternoon with a ride on the iconic cable cars up to Nob Hill, where you can sip a cocktail at the elegant Top of the Mark while watching the sunset over the city.
As twilight settles, stroll to the historic Tadich Grill on Columbus Avenue for a classic seafood dinner, then wander into lively North Beach to savor a creamy gelato at Gelateria Naia while the evening buzzes with live jazz at The Beatnik. End the night with panoramic city lights from the View Lounge atop the Marriott Marquis, toasting the adventure with a glass of locally sourced California Pinot Noir.
After a scenic 1½-hour drive north, enjoy a leisurely breakfast at Bouchon Bakery in charming Yountville, where flaky croissants pair perfectly with freshly brewed espresso. Then set off for a sparkling start at Domaine Carneros, strolling through its elegant terrace while sipping crisp Champagne-style wines before heading to the medieval-themed Castello di Amorosa for a guided tour and a tasting of their renowned Cabernet Sauvignon.
After lunch, drive to the iconic Opus One estate in Oakville for an intimate seated tasting of their flagship Bordeaux-blend while admiring the rolling hillside vistas. Then wander to V. Sattui Winery in St. Helena for a relaxed cheese board paired with a crisp Sauvignon Blanc, and cap the afternoon with a leisurely stroll along the historic Napa Riverfront, sipping a refreshing spritzer at the waterfront café.
After a day of tasting, head to Cade Estate in Napa for a sunset tasting paired with artisanal small plates, then wander to the bustling Oxbow Public Market to sample local cheese boards and a glass of sparkling Petite Sirah. End the night with a rooftop cocktail at Sky & Vine overlooking the illuminated vineyards, where you can toast the day's adventures under the stars.
Kick off the morning with a hands-on farm-to-table cooking workshop at The Culinary Institute of Napa Valley, where a local chef helps you craft fresh bruschetta and seasonal salads using produce from Rutherford Farm. Afterward, wander to Stag's Leap Wine Cellars for a seated tasting of their legendary Cabernet Sauvignon paired with artisanal cheese. Wrap up with a light brunch of avocado toast and a glass of crisp Chenin Blanc at the scenic Napa Valley Wine Train Bistro.
After the workshop, stroll to Bottega Napa Valley for a leisurely al fresco lunch of wood-fired pizzas paired with a crisp Sauvignon Blanc from their own label. In the early afternoon, head to Duckhorn Vineyards in St. Helena for a seated tasting of their signature Merlot, complemented by a small-plate cheese board featuring local goat cheese. Finish with a sweet indulgence at Chocolate Factory Napa, where you can craft your own truffle while sipping a glass of late-harvest Riesling.
As the sun dips behind the hills, unwind with a sunset tasting of premium Pinot Noir and small-plate charcuterie at Artesa Vineyards & Winery, where the panoramic views set a magical backdrop. Afterwards, stroll to Farmstead at Long Meadow Ranch for a farm-to-table dinner featuring wood-grilled ribeye and seasonal vegetables, then cap the night with a relaxed nightcap on the patio of The Barrel Room, sipping a smooth Cabernet Franc under the stars.
Begin the day unwinding at the tranquil Calistoga Ranch Spa, where you can soak in the geothermal mineral pool and indulge in a signature volcanic stone massage that awakens the senses. Afterwards, stroll to the nearby Solage Calistoga for a rejuvenating Himalayan salt-cave session followed by a refreshing cucumber-mint facial, leaving you ready for a leisurely afternoon among the vines.
After your morning at the spa, take a short drive to Bothe-Napa Valley State Park for a gentle redwood hike and a peaceful pause at the Bodega Creek overlook. Next, wander to Mumm Napa in Oakville for a seated tasting of their celebrated Brut Rosé, complemented by selections from the on-site cheese cellar. Conclude the afternoon with a tranquil sunset paddle on the Napa River with Napa Valley Paddle Company, letting the calm currents and vineyard-lined banks ease you into evening relaxation.
After a day of pampering, head to Auberge du Soleil for a candlelit dinner on the terrace, where the chef's seasonal tasting menu is paired with exquisite estate wines and offers sweeping views of the valley. Post-dinner, stroll down to Cadet Wine & Beer Bar in downtown Napa to sample a curated selection of small-batch rosés and craft brews while live jazz fills the intimate space. Cap the night with a quiet moment on the rooftop of Madrone Lounge, sipping a silky Pinot Noir as the lights of the vineyards twinkle below.
At sunrise, glide over the vineyards with Napa Valley Balloon Rides, letting the pilot point out the sweeping vistas of Mount St. Helena as the valley awakens. After a gentle landing, celebrate with a glass of sparkling rosé and fresh pastries at the historic Chateau Montelena tasting room, setting a breezy, celebratory tone for the day.
After the balloon touchdown, treat yourselves to a farm-to-table lunch at Robert Mondavi Winery's Olivier Restaurant, where a glass of their signature Fumé Blanc pairs perfectly with seasonal dishes. Next, wander the Napa Valley Museum in Yountville for a concise, captivating look at the region's winemaking heritage. Wrap up the afternoon with a leisurely tea on the Caymus Vineyards terrace, sipping a buttery Chardonnay while the vines sway in the golden light.
After the sunrise balloon adventure, drift to Domaine Chandon for a twilight sparkling-wine tasting on its terraced patio, then savor a farm-to-table dinner at Meadowood Napa Valley where each course is paired with estate selections. Finish the evening with a cozy cocktail at Cask in downtown Napa, where live acoustic music and a warm fireplace round out the day's memorable views.
Start the morning with a leisurely brunch at The Rotunda in Neiman Marcus on Union Square, savoring their famed almond croissant and a glass of fresh-pressed Napa Valley Chardonnay. Afterward, stroll down Market Street to the historic Cable Car Turnaround for one last ride up to Fisherman's Wharf, where you can snap a quick photo with the sea lions at Pier 39 before catching the BART to San Francisco International Airport for your afternoon flight home.
Spend your final afternoon unwinding in the sleek Grand Hyatt at SFO lounge, where you can sip a chilled Napa Valley rosé while browsing the curated art exhibits of the SFO Museum. Treat yourself to a gourmet bite at The Mill, famed for its artisanal pastries and locally roasted coffee, then explore the waterfront-themed Yankee Pier for a last glimpse of the Bay before boarding. Finish with a quick browse of the boutique Vino Vault for any last-minute wine souvenirs.
Before boarding your flight, indulge in a farewell dinner at Murray Circle inside the historic Fairmont San Francisco, where panoramic city lights and a curated tasting menu of locally sourced seafood create a perfect send-off. Afterwards, sip a smooth cocktail at the chic Starlight Room atop the Sir Francis Drake Hotel, soaking in the glittering skyline as you cap off the adventure.