Over The Top Wine Tasting Experiences

Close your eyes, point to any one of the more than 800 wineries on the Napa Valley and Sonoma County winery maps, and there is little doubt that your blind selection yields a wonderful wine tasting experience. Most of the region’s wineries welcome guests with open arms, offering gracious hospitality within their verdant vineyards. But a few wineries and winemakers go a step further, immersing wine lovers in the vinous process while revealing their secrets to success. Others roll out a virtual red carpet, creating elegant, otherworldly environments in which to escape, if only for an hour or two. And one Napa Valley vintner soars (quite literally) to new heights with her elevated wine tastings. If you are one not easily gratified by a routine sampling of Napa Cab, these wine tasting experiences are for you.

Aileron proprietor Shannon O’Shaughnessy. Photo by Bob McClenahan

Aileron Estates Take Flight Experience

Aileron Estate’s wines are alone worthy of a wine country visit. Add a pre-tasting, scenic bi-plane ride over Sonoma, and Aileron becomes a wine tasting must-do. Take Flight pairs Aileron proprietor Shannon O’Shaughnessy’s luxe Cabernet Sauvignon and Sauvignon Blanc with soaring, open air heights, provided by the skilled pilots of Vintage Aircraft in Carneros, and the combo is exhilarating. O’Shaughnessy’s own passion for flight led to the creation of the unique offering. Take Flight is offered in partnership with Vintage Aircraft and includes a 20-minute scenic flight, including aerobatics (inverting, Barrel Rolls, a Hammer Head, and a Cuban Eight) if desired, followed by a private tasting at Brasswood Estate of Aileron’s first two vintages, made by the rock star winemaking team of Philippe Melka and Mayan Koschitzky of Atelier Melka. ($550 per person)

Theorem Vineyards Baccarat Experience. Photo courtesy of Theorem Vineyards

Theorem Vineyards Baccarat Tasting Experience

Life’s landmark occasions often call for an equally momentous celebration. Napa Valley’s Theorem Vineyards holds the key for a splurge-worthy solution. The luxury winery has teamed up with renowned French glassware artisans Baccarat Crystal to create the Theorem Vineyards Baccarat Tasting Experience, offering celebrants a sumptuous, one-of-a-kind wine and food exploration enhanced by luxurious Baccarat crystal. A guided walking tour of Theorem’s Diamond Mountain property culminates at one of the winery’s scenic outdoor lookout points, or in the soaring, open air tank room, where a dazzling table festooned with fine linens, fresh-cut flowers in a Baccarat vase, Baccarat candlesticks, and a selection of Baccarat’s celebrated stemware awaits. The tablescape is further enhanced by three of Theorem’s high-elevation, estate bottlings served with seasonally-inspired food parings prepared exclusively for the occasion by Theorem’s culinary director Chef Josh Mitchell. For added indulgence, participants are invited to choose one of the elegant Baccarat wine glass styles for themselves, to be engraved with a meaningful phrase. ($750 per person)

Bouchaine winemaker Chris Kajani with falcon Mariposa. Photo courtesy of Bouchaine Vineyards

Bouchaine Vineyards Falconry Experience

This exclusive opportunity allows guests to witness firsthand the wonder of nature in support of sustainable farming practices. Working with West Coast Falconry, Northern California’s premier resource for falconry education and services, Bouchaine Vineyards, via its Falconry Vineyard Experience, allows participants to learn about the role of raptors in vineyard management, while enjoying a glass of wine. The falcons swoop through the air in a display of astonishing agility, return to their handler, and then to the gloved arm of each guest as the falconer discusses the eyesight, flying, and hunting techniques of hawks, falcons, owls, and eagles. ($75 per person)

Immortal Estate 100-Point Experience. Photo courtesy of Immortal Estate

Immortal Estate 100-Point Experience 

Immortal Estate is a luxury Sonoma wine brand from Tim Martin of Tusk Estates and Randy Nichols, developer of Napa’s new Auberge Resort at Stanly Ranch Carneros. Their 100-Point Experience takes place in Napa at a private, undisclosed Rutherford location and includes pours of four vintages of their flagship Cabernet Sauvignon, Impassable Mountain, including the 2013 and 2016 vintages, which were each rated 100 points by both Robert Parker of the Wine Advocate and critic Jeb Dunnuck. This immersive dive into these world class wines is for groups of four to eight. ($500 per person)

TOR Black Magic Experience. Photo courtesy of TOR

TOR The Black Magic Experience

Tor Kenward’s more than four decades in the wine business has culminated in a wine so outstanding, it was awarded four 100-point scores by varied industry critics. Guests indulging in The Black Magic Experience can sample that wine – the 2018 Black Magic – while gaining entry to a behind-the-curtain peek into the life of a vintner at the top of his game. David Grega, TOR’s longtime associate winemaker, hosts this exclusive tour of the hallowed soils of the legendary Vine Hill Ranch, Beckstoffer Dr. Crane, and Beckstoffer To Kalon vineyards, from which Kenward sources his grapes. The tour is followed by a luxe culinary experience. ($950 per person; four person minimum)

TOR Pritchard Hill Hike. Photo courtesy of Suzanne Becker Bronk

TOR Pritchard Hill Hike & Flight

Greg Melanson’s Pritchard Hill vineyard is prime real estate for world-class Cabernet Sauvignon. Perched approximately 1500 feet above the valley floor, the vineyard shares esteemed neighbors such as Colgin, Continuum, and OVID. This stunning and rugged site is typically not open to the public, but Melanson allows TOR guests access to the magnificent views. Hike the vineyard’s steep grade to better understand the nuances of Pritchard Hill Cabernet, and afterward enjoy a tasting of three vintages of TOR’s spectacular Melanson Cabernets paired with small bites. ($350 per person, four person minimum) 

Cliff Lede Diamond Luncheon Experience. Photo by Bob McClenahan

Cliff Lede Anthology + Diamond Luncheon Experience

For the discerning wine collector who appreciates rarity, the Anthology Experience showcases a collection of Lede’s small production, critically-praised Platinum Playlist and select library wines. Sourced from the most prized vineyards in the Napa Valley, these wines represent the apex of Cliff Lede’s portfolio. Amp-up this tasting with the Diamond Luncheon Experience, a family style luncheon in one of Lede’s beautifully atmospheric venues surrounded by intriguing artwork hand-selected by Lede himself. ($450 per person, eight person minimum)

Twilight at Trefethen Experience. Photo courtesy of Robb McDonough

Twilight at Trefethen 

One of Napa’s pioneering wineries, Trefethen Family Vineyards was founded in 1968 by Janet and John Trefethen. More than five decades later, this venerable Napa winery remains family-owned and committed to the craft of producing 100% estate-grown wines. The winery is also committed to providing outstanding wine tasting experiences, such as its Twilight at Trefethen, where guests can experience and explore the beautiful Oak Knoll family estate in private. A tour is followed by a seated tasting of five of Trefethen’s finest wines paired with delicious bites crafted by Trefethen’s Executive Chef Chris Kennedy. ($200 per person)

Far Niente Winery. Photo courtesy of Far Niente

Far Niente Cave Collection Library Wine Tasting 

Experience Far Niente’s legendary Cabernets in one of the most enchanting settings in wine country. Showcasing three beautifully aged, highly limited Far Niente Cave Collection Cabernets, the Cave Collection Library Wine Tasting also invites you to discover current and cave vintages of Far Niente Chardonnay and ends with a taste of their late harvest jewel, Dolce Napa Valley. Each wine is masterfully paired with curated small bites. The private tasting experience is led by one of Far Niente’s professional hosts and includes a tour of the wine caves and wine library as well as an invitation to enjoy the gorgeous winery gardens at leisure. ($200 per person)

Stag’s Leap Wine Cellars Cellarius Kitchen Experience. Photo courtesy of Stag’s Leap Wine Cellars

Stag’s Leap Wine Cellars Cellarius Experience

Held on Stag’s Leap Wine Cellars’ elegant kitchen patio, the Cellarius Kitchen Experience pairs the winery’s world-renowned labels with four delectable courses, each made with locally sourced, seasonal ingredients by executive Chef Travis Westrope who knows the Stags Leap District well and understands how to highlight the unique characteristics of Stag’s Leap Wine Cellars wines. Westrope harnesses the individuality of the wines (2018 CASK 23 Cabernet Sauvignon, 2018 S.L.V. Cabernet Sauvignon, 2018 FAY Cabernet Sauvignon, and 2017 ARCADIA VINEYARD Chardonnay) to create dishes that both complement and contrast their flavors and aromas. During the experience, Westrope, or a member of his culinary team, shares the story behind each food pairing, linking the dish to the wine. This year, in celebration of the 45th anniversary of The Judgment of Paris, at which Stag’s Leap Wine Cellars was the red victor, Westrope’s menus are French inspired. ($195 per person)

Acme Fine Wines St. Helena Tasting Room. Photo courtesy of Acme Fine Wines

ACME Fine Wines Cult v. IPO Tasting

St. Helena-based ACME Fine Wines is known for its role in helping to launch and promote micro-wineries and brands that ultimately achieve great fame. Internally dubbed “IPO” brands, these are debut projects carefully chosen by ACME’s dynamic team of sommeliers who constantly scout to bring the next big thing to their clients – before anyone else. This Cult v IPO Tasting features two cult wines (think brands like Harlan Estate, Screaming Eagle, and Scarecrow) alongside two soon-to-be-discovered IPO wines. Let ACME’s somms guide you through this tasting of Napa’s best and what’s next; includes a charcuterie and cheese platter. ($500 per person, six person minimum) 

Obsidian Wine Co. Oyster Harvest. Photo courtesy of Obsidian Wine Co.

Obsidian Wine Co. Outdoor Adventure Series

This Sonoma winery’s Outdoor Adventure Series was created by Obsidian’s founders to help guests enjoy wine outdoors, in nature. Past and future adventures include hiking a volcano with a professional geologist, harvesting oysters at the edge of Tomales Bay with Hog Island Oyster Company, hand picking Pinot Noir grapes alongside the Obsidian vineyard team, and participating in a saffron harvest at Peace & Plenty Farm in Kelseyville, with a paella meal afterward. (price varies per experience)

Cultured Vine Bespoke Experiences. Photo courtesy of Cultured Vine

Bespoke Experiences, Curated by Cultured Vine

Let luxury concierge service Cultured Vine help you plan your dream wine tasting adventure. Cultured Vine founder Angela Duerr knows that when it comes to extraordinary wine and food, one size definitely does not fit all. Duerr and her team specialize in creating and curating exclusive experiences that include behind the scene visits not open to the public, helicopter escapes, private chef dinners, and nearly whatever your heart desires. “I come up with things that you couldn’t have done on your own,” said Duerr. “No two experiences are ever alike.”


Fran Miller

Fran Endicott Miller is an experienced travel, wine, and general feature writer for a variety of luxury lifestyle publications and websites. Prior to her journalism career she established and managed the Golden State Warriors' first official community relations department and efforts. Principled and genuine, she’s known for thoughtfully eloquent writing. When not traveling, she can be found walking her Northern California neighborhood with her beloved golden retriever Nate.