2025 Auction Lots

Below is a listing of the amazing 2025
Naples Winter Wine Festival auction lots

Flexjet Raffle 2025

5 – 750ml Château Cos d’Estournel (1 each: 2005, 2017-2020)
4 – 750ml Château Pichon Baron (1 each: 2017-2020)

Eight (8) night luxurious sun and ski adventure with Montage with four (4) nights in Los Cabos, Mexico plus four (4) nights in Big Sky, Montana for three (3) couples

Roundtrip, Private Air from Naples, Florida to Los Cabos, Mexico on a Flexjet Challenger 300
Roundtrip, Private Air from Naples, Florida to Big Sky, Montana on a Global 6000
Roundtrip, airport transfers and ground transportation to all stated activities

Los Cabos, Mexico:
Four (4) nights’ accommodations in a Three (3) Bedroom Residence at Montage Los Cabos
One (1) private four (4) hour cruise on a 56’ Twin Dolphin VanDutch yacht, including select snacks and alcoholic and non-alcoholic beverages
One (1) hour private Mexican cooking class
One (1) hour private agave tasting experience
One (1) 60-minute massage or facial spa treatment per person at Spa Montage Los Cabos
Breakfast included daily

Big Sky, Montana:
Four (4) nights’ accommodations in a Three (3) Bedroom Residence at Montage Big Sky
Private tour of Yellowstone by car or by horseback
Winners’ choice of either dog sledding in winter or one (1) round of golf at Spanish Peaks Mountain Club, including club rentals, in summer
One (1) 60-minute massage or facial spa treatment per person at Spa Montage Big Sky
Breakfast included daily

 

Three couples will experience the unique world of Montage Hotels & Resorts in two very different and distinctive locations: Los Cabos, Mexico and Big Sky, Montana.

Designed to serve the affluent and discerning traveler, Montage is a collection of artistic hotels, resorts and residences. This lot is perfect for multiple couples traveling together or a multi-generational family trip. Guests can expect impeccable hospitality, exceptional epicurean experiences, world class spas and an elegant yet welcoming ambiance.

The winning bidders’ party will travel by private jet on a Flexjet Challenger 300 to Los Cabos, at the southern tip of Mexico’s Baja California Peninsula. Your home at Montage will be a stunning Three Bedroom Residence spanning more than 4,000 square feet. The chef’s kitchen features a large island and a separate indoor dining table. Open plan living and dining rooms with sliding doors provide an easy transition to outdoor living space that includes a large terrace with an additional dining table for six, gas fire pit, summer kitchen and Wolf BBQ.

For the next few days, you’ll bask in the delights of Los Cabos, where the desert meets the sea.

You’ll sail the Sea of Cortez on a 56-foot VanDutch boat charter. VanDutch yachts are crafted in Italy with both passion and precision. You’ll indulge in personalized amenities like a bespoke onboard bar and a selection of snacks. A beautiful deck space allows guests to relax and enjoy every moment in freedom and autonomy.

Your party will explore the rich traditions of Mexican cuisine through a cooking class led by an expert chef. Uncover the secrets behind age-old recipes, cherished across generations, as you discover the art of crafting authentic dishes bursting with flavor. On another day, guided by in-house spirit connoisseurs, embark on a journey through the storied history of agave, savoring each moment sip by sip. Immerse yourself in tastings of regional Mexican spirits crafted from agave, including Sotol, Bacanora, Mezcal, Raicilla and Tequila.

At a separate time, you will board a Global 6000 for a private flight to the Montage resort in Big Sky, Montana, where you’ll experience the natural beauty and adventurous spirit of the Mountain West.

In Big Sky, you’ll sleep in a luxurious, fully equipped Three Bedroom Residence with sweeping views of the surrounding peaks. Enjoy a VIP tour of Yellowstone, established in 1872 as the first national park in the world, and marvel at the flora and fauna of the largest continuous stretch of undeveloped, pristine land in the contiguous United States. Expert naturalist guides will take you along scenic routes and lead you past majestic geysers, wildlife and waterfalls.

If you want to see Big Sky Country from a new perspective, sample the world of dog sledding. Receive firsthand knowledge on the art of mushing and canine training before you embark on an unforgettable journey through breathtaking landscapes. If you’re a golfer, try out the course at Spanish Peaks Mountain Club, set at 7,000 feet above sea level. Designed by Tom Weiskopf, the 18-hole course features a remarkable combination of playability, challenge and mountain views.

Whether you choose rugged outdoor activities or the refined elegance of the alpine-inspired spa, Big Sky will renew your spirit.

As a cellar treasure, the winning bidders will receive vertical collections of Château Cos d’Estournel and Château Pichon Baron. Located respectively in Saint-Estèphe and Pauillac, both estates were ranked as Second Growths in the Classification of 1855 and will age gracefully for years to come.

Experience the art of travel in very special yet diverse ways and contribute to the future of our children at the same time.

Insider's Info

This lot is for three (3) couples or six (6) individuals. The accommodations at each property include a Three (3) Bedroom Residence and bed configurations vary based on availability and request. Visits to be scheduled for mutually agreeable dates and based on availability. Visits to Los Cabos and Big Sky to be taken at separate times. Blackout dates at Montage Los Cabos include holidays or holiday weekends and dates including, but not limited to, March 9-16, 2025; April 18-22, 2025; November 25-30, 2025; and December 18, 2025-January 5, 2026. The Flexjet Private Air to Los Cabos must be scheduled at least thirty (30) days in advance and blackout dates in 2025 include but are not limited to January 2-5, 14, 21, 25 and 28; February 1, 4, 8, 11, 13-14, 16-18 and 25; March 1-2, 4, 8-9, 11, 15-16, 18, 22-23, 25 and 29-30; April 1, 5, 7-8, 22, 26 and 29; May 3, 6-7, 10, 13-14, 17, 20, 23-24, 26 and 31; June 3, 7, 9-10, 14, 17-18, 21 and 24-26; July 3-5 and 7; August 29-30; September 1-2; October 10-11 and 14; November 22-27 and 29-30; and December 1-2, 7 and 19-31. Additional blackout dates will be released for the second half of 2025 at a later date. Flexjet requires at least 48-hours notice for any changes to the flight itinerary. Additional blackout dates will be released for the second half of 2025 at a later date Blackout dates at Montage Big Sky include Fridays, Saturdays, holidays and holiday weekends and dates including but not limited to December 18, 2025-January 6, 2026. Auction lot expires January 25, 2026. Gift certificates for each property cannot be sold or transferred and must be presented at time of redemption. Meals are only included as stated above. Breakfast and spa treatments are inclusive of taxes and gratuity. Additional gratuities are not included.

Donor

Montage Big Sky and Montage Los Cabos
Private Air donated by Flexjet, LLC and Shelly & Ralph Stayer

  • Stay in the loop

    Join our mailing list for updates, news and more.