Red revels in photos that tell a story, particularly those that reveal family heritage and history. This lot provides plenty of both: the sophistication of Santiago and the rise of a remarkable new winery in Chile’s Millahue Valley, along with the amazing saga of the Novak family in Napa.

Two couples will explore the wonders of Chile in supreme comfort and experience the legacy of Napa’s Spottswoode winery. You’ll fly to Santiago, Chile’s historic capital founded in 1541, and spend two nights at the Mandarin Oriental, relaxing in Grand Terrace Suites with over 1,500 square feet of luxury. The following day, you’ll travel to the Maipo Wine Valley for a tasting and lunch at Doña Paula, producer of vibrant Malbec. That evening, you’ll dine at Boragó, one of South America’s top restaurants, renowned for ingredients sourced from local producers.

Your final destination in Chile is the Millahue Valley in the O’Higgins region, home to the Viña VIK winery and the VIK Hotel. Founded in 2006 by Alexander and Carrie Vik, the winery specializes in Bordeaux varietals and blends, including Vik, Milla Cala and La Piu Belle. The striking resort in the vineyard is regarded as one of the country’s finest places to stay. You’ll receive a tour and tasting at the winery and have full access to the resort’s amenities, including picnics in the organic gardens, horseback riding, swimming, hiking and biking. During your stay, you’ll also take advantage of the exceptional gastronomic restaurants on the property.

At a separate time, your Napa Valley journey will begin with three nights at the boutique hotel Southbridge Napa Valley, located in the heart of St. Helena. Guests will start each day with a complimentary breakfast of fresh pastries and locally roasted coffee. Throughout the stay, you’ll have access to Health Spa Napa Valley’s lap pool, steam rooms and fitness center. A welcome dinner with Spottswoode Proprietor Beth Novak at Goose & Gander, a beloved local favorite just steps from your hotel, will be the perfect way to spend your first evening in Napa.

The following morning, you’ll be welcomed at the winery for a private tour and tasting. The highlight of your stay will be an exclusive dinner that evening hosted by Beth in the Novak family home, offering wines from their library and a rare glimpse into the warmth and legacy of one of Napa’s most storied families. On your final day, the winery concierge will arrange a tasting at one of Napa’s hidden gems, followed by dinner at one of Spottswoode’s highly regarded local restaurant partners.

The modern story of Spottswoode began in 1972, when Mary and Jack Novak purchased a vineyard in St. Helena first planted in 1882. Jack passed away soon after, leaving Mary to establish the estate on her own. She persevered and released her first vintage in 1982 to celebrate the centennial of the property. Since then, Spottswoode has become one of Napa’s great wines, earning every possible accolade.

Today, the business is still family-run by Mary’s daughters, Beth and Lindy. The small production focuses on Sauvignon Blanc and Estate Cabernet Sauvignon, along with limited releases of Mary’s Block Sauvignon Blanc, Lyndenhurst Cabernet Sauvignon and the Field Book red blend. Spottswoode has also led the way in environmental stewardship, farming organically and consulting with biodynamic experts.

To remind them of their time at Spottswoode, each couple will take home bottles of Estate (Mary’s Block) Sauvignon Blanc and a mini-vertical of Estate Cabernet Sauvignon, in both regular and Magnum format.

Red promises that this exceptional lot will deliver the very best in food and wine, along with history, heritage and respect for the land—qualities we hope to pass on to the next generation.

Insider’s Info

These trips are for two (2) couples. Visits to be scheduled for mutually agreeable dates and based on availability. Blackout dates in Napa include the months of September and October. Blackout dates in Chile include December 23, 2026-January 3, 2027. Airfare to Napa is not included. One (1) roundtrip group airport transfer is included in both Napa, California and Santiago, Chile. Guests arriving or departing separately will be responsible for the costs of any additional transfers. Transportation to stated activities is not included in Napa. The wine tasting at VIK Vineyard will be with a VIK Vineyards team member. The spa treatment in Napa will be any 50 or 80-minute massage or facial up to $245 in value and includes gratuity. Complimentary breakfast pastries and coffee are included in Napa each day. Meals are only included as stated above. Select wines and non-alcoholic beverages are included with the stated dinners. Any additional meals and beverages are not included. Gratuities are included for stated meals and spa treatments in Napa. Any additional gratuities are not included in Napa or Chile.