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From Cliffside to Cabernet: Big Sur and Napa Valley
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IntroStayHighlightsitinerary
From the rugged cliffs of California’s Central Coast to the vine-covered hillsides of Napa Valley, this dual-destination itinerary blends two of the Golden State’s most iconic landscapes into one seamless journey.
If you’re looking for a Big Sur and Napa Valley itinerary, you’ve come to just the right place. This customizable sample itinerary will wind you through the restorative pull of Big Sur’s untamed beauty, followed by the laid-back sophistication of wine country living, with both stays brought to life through Alila’s signature blend of eco-conscious luxury, place-inspired experiences, and thoughtful hospitality.
Your adventure begins at Alila Ventana Big Sur, an all-inclusive adults-only retreat perched high above the Pacific. Here, mornings unfold beneath towering redwoods with guided meditation and coastal hikes, afternoons invite creative workshops or time at Spa Alila, and evenings end with starlit dinners celebrating the bounty of California’s Central Coast. The pace is intentionally slow, encouraging you to disconnect from the noise and reconnect with nature, your senses, and yourself.
From Big Sur, you’ll trade ocean vistas for vineyard views at Alila Napa Valley in the charming town of St. Helena. This intimate, adults-only sanctuary pairs contemporary design with the timeless rhythms of wine country. Days here are made for sunrise hot air balloon rides, vineyard-side spa rituals, curated wine tastings, and Michelin-starred dining. Whether exploring the valley’s celebrated wineries or unwinding by the pool with a reserve Cabernet in hand, every moment is designed to indulge and inspire.
While completely customizable, this sample itinerary is a six-day itinerary meant to maximize immersion into the region's wine and nature.
Trip Style
This journey blends barefoot luxury with refined indulgence, taking you from the wild, wind-swept cliffs of Big Sur to the sun-drenched vineyards of Napa Valley.
We Love It For
Perfect for nature lovers, wellness seekers, culinary enthusiasts, and romantics alike, this itinerary offers the best of California’s coastal and countryside charms—each destination distinct, yet connected by Alila’s commitment to purposeful luxury and a deep respect for the land. The result? A journey that leaves you feeling both grounded and elevated, with memories as vivid as the landscapes themselves.
Scouting Notes
Work with your SmartFlyer travel advisor to book a Pacific-facing suite at Ventana for golden hour light that feels cinematic—best enjoyed from the deck with a glass of local Pinot Noir. In Napa, we love a second-floor vineyard view room at Alila for a balcony vantage point over Beringer’s vines, especially magical at sunrise before the valley stirs.
Perched high above the Pacific Ocean, Alila Ventana Big Sur is an all-inclusive, adults-only resort where rustic elegance meets refined comfort. Surrounded by ancient redwoods and dramatic coastal vistas, the property features Japanese hot baths, two outdoor pools, Spa Alila, and The Sur House restaurant. Immersive daily programming—like guided meditation, foraging hikes, beekeeping, and artistic workshops—connects guests to the land in meaningful ways. With gourmet meals, snacks, and non-alcoholic beverages included in the rate along with direct access to scenic hiking trails and elevated wellness offerings, each stay fosters a seamless, restorative connection to nature.
Nestled beside the storied Beringer Vineyards in St. Helena, Alila Napa Valley offers sixty-four serene, design-forward rooms, each opening to sweeping vineyard views. The acclaimed Violetto restaurant showcases the region’s bounty through refined French-Italian cuisine, while the spa offers restorative treatments inspired by the land’s natural elements. Designed by Yabu Pushelberg, the resort blends Napa’s laid-back elegance with modern sophistication, creating an intimate sanctuary in the heart of wine country.
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Highlights
Scenic drive along Highway 1 capped by a seasonal dinner with sweeping Pacific views at The Sur House.
Day 1
Guided meditation beneath the redwoods followed by a coastal hike and hands-on workshop.
Day 2
Picnic stop at historic Oakville Grocery en route to vineyard-view relaxation at Alila Napa Valley.
Day 3
Sunrise hot air balloon ride over the valley’s patchwork of vineyards.
Day 4
ItineraryItinerary
1
Arrival and Immersion in Big Sur
Your journey begins along the legendary Highway 1, where the drive itself is part of the experience. Pause at iconic viewpoints like Point Lobos State Natural Reserve, Garrapata State Park, and the photogenic Bixby Bridge before arriving to check in at Alila Ventana Big Sur. Settle into your suite, designed to frame the surrounding redwoods and ocean vistas.
As the late afternoon light shifts, wander the organic garden, take a dip in the Ocean Meadow Pool, or simply breathe in the crisp coastal air. Dinner at The Sur House acts as a celebration of the Central Coast’s bounty—expect seasonal, hyper-local dishes paired with sweeping Pacific views. End the evening with stargazing or a tranquil soak in the Japanese hot baths.
2
Nature, Nourishment, and Creative Expression
Begin your morning with a guided meditation under the redwood canopy, grounding you in the day ahead. A leisurely brunch at The Sur House follows, best enjoyed with uninterrupted ocean views. Late morning brings a guided hike along one of Big Sur’s famed trails, where rugged cliffs meet towering forests. The afternoon is yours to shape: join a creative workshop like beekeeping or natural soap making, or indulge in a signature treatment at Spa Alila. As the sun dips low, an al fresco dinner awaits, each course thoughtfully paired with local wines.
3
Farewell Rituals and Last Looks
Savor your final morning at Alila Ventana Big Sur with a room service breakfast, followed by one last walk among the redwoods or a soak in the Japanese hot baths. Linger in the shared spaces at your leisure to soak in the stillness before beginning your journey north, sure to leave Highway 1 with a fresh perspective—the kind that only Big Sur can inspire.
Arrive in Napa Valley and stop at the historic Oakville Grocery—California’s oldest continually operating grocery store—to pick up artisanal cheeses, charcuterie, and a bottle of local wine before checking into Alila Napa Valley, where your suite opens onto postcard-perfect vineyard views. A signature treatment at Spa Alila sets the tone for relaxation, followed by a light lunch or cocktail on the Salvia Terrace. In the afternoon, enjoy a private tasting at Beringer Vineyards’ Rhine House, just steps from the resort. Unwind by the heated pool before an indulgent, wine-paired dinner at Violetto, where French-Italian influences meet Napa’s freshest ingredients.
4
Elevated Exploration
Rise early for a sunrise hot air balloon ride, which will find you floating over a patchwork of vineyards bathed in golden morning light. Return to the resort for a leisurely brunch and poolside downtime. The afternoon invites exploration—perhaps tastings at Rutherford Hill Winery or Oakville estates such as Alpha Omega Winery or PlumpJack Estate Winery. Tonight, a table awaits at PRESS, Napa’s first Michelin-starred restaurant, where the region’s finest wines meet impeccable, locally sourced cuisine. End the night by your terrace fireplace under a canopy of stars.
5
Departure and Final Moments in Napa
Your final morning is for slow indulgence—coffee on your terrace, a restorative spa ritual, or even a private falconry session on the resort grounds. After an unhurried breakfast, check out, and if time allows, the concierge can arrange one last tasting or scenic stroll before you depart, carrying with you the warmth and beauty of wine country.
