Special Event Live Auction

We believe in our students and the value of an Oakwood education. The powerful personal discoveries our students make while at Oakwood are enriched by the collective generosity of families like yours.

Your generous support of the financial assistance program will impact the lives of our students and helps support current and future generations at Oakwood School. THANK YOU!


Nestled between scenic mountains and the Mediterranean Sea, your group of 8 will discover Barcelona’s remarkable history, witness its striking physical beauty, and savor the region’s incredible gastronomic traditions. Explore the vibrant, ever-changing port city of Barcelona, Spain, with its energetic atmosphere—a convergence of culture, fun, and gourmet food! 
As the capital of Catalonia, the autonomous region of Spain, you will find that Barcelona has its own unique, fascinating traditions and language. Its mild Mediterranean climate means life is mostly enjoyed outdoors, on the streets, creating a lively vibe that welcomes you in. You will be surrounded by artistic treasures from its extraordinary history as well as the great names in modern art and architecture. Barcelona’s dynamic cuisine has developed over the centuries from various influences abroad, resulting in a melody of dynamic flavors that will absolutely delight you. Without a doubt, Barcelona is one of those cities that you must visit at least once in your lifetime. This vibrant, ever-changing port city has an energetic atmosphere and is a concentration of culture, fun, and incredible gastronomic traditions that make it a paradise for gourmet lovers, with plenty of renowned chefs and mindblowing food markets.
Your beautiful countryside villa for the week is 12 miles outside of Barcelona, just a short distance from the Mediterranean Sea. This lovely stone residence with 4 bedrooms / 4 bathrooms offers your group an elegant, quiet contrast to the city and plenty of space to relax. Here you can lounge on cushy sofas on the spacious outdoor terrace, stroll in the lovely curated garden, and refresh yourself in the private swimming pool. You can also bask on the beautiful Mediterranean beaches nearby or immerse yourselves in nature in two large natural parks.
The region surrounding Barcelona is well known for the production of great wines with the most famous being the cava wines. However, the area is also appreciated for other fantastic wines known as sea wines, due to the strong influence of the Mediterranean sea on the characteristics of the wine. You will visit one of the most well-known wineries in the region and have the chance to taste 4 different wines, all while enjoying the beautiful views of the Mediterranean Sea
Barcelona has distinguished itself around the world for its spectacular cuisine, based on the fresh and healthy ingredients of the Mediterranean diet. You will get to relax and enjoy a traditional dinner, right in the comfort of your villa, where a private chef will prepare a deliciously tantalizing 3-course meal for you!
This 3-hour experience will bring you to see the area where Barcelona was born over 2000 years ago, and that is still one of the most dynamic parts of the city today. Your private guide will also take you to two food stops, the first one in the Mercado de la Boqueria to sample Cava wine paired with Jamon Bellota ham and the other will be dedicated to typical tapas and vino tinto.
A member of our staff will always be at your disposal before and during your holiday for trip details preparation and arranging free time for extra activities and services
  • 7 nights in a lovely villa near Barcelona
  • Dinner in the villa with a private chef
  • Winery visit with tour and tasting
  • 3-hour private guided walking tour of the Gothic quarter with 2 food stops
  • Concierge service and travel assistance
Restrictions and Details: Hola Barcelona is a vacation package of 7 days and 7 nights for a maximum of 8 guests. Please consider that it is very important to book your vacation within one month of the auction. Bookings are based on the availability of accommodations and must be redeemed by March 19, 2024. There is no refund for unattended or guest-canceled services. Airfare, ground transportation, and activities not listed in the inclusions are not included. Extra services can be arranged separately for an additional fee.
Value: Priceless

Mozza the Merrier! The Dinner Party of a Lifetime for 16 prepared by Nancy Silverton

Your group of 16 will win a delicious multi-course dinner with wine pairings for 16 prepared by parent of alumni, Chef Nancy Silverton, in the private Jack Warner Room at Osteria Mozza! 
Chef Nancy Silverton needs no introduction - Osteria Mozza, Pizzeria Mozza, and chi SPACCA are just a few of the examples that helped change the food and dining world in Los Angeles and beyond. Your group will savor each bite presented by Nancy in her signature space. Nancy will not only cook, but will also guide you through a journey of culinary delights. Each guest will also receive a signed cookbook from Chef Nancy.
Osteria Mozza is a melding of the charm of the rustic past with the sleekness of the thrilling modern. From the moment a diner opens the front door on Highland and Melrose Avenues, Osteria Mozza transports them to a comforting atmosphere alive with the anticipation of a great dinner. From exquisite handmade pasta to Grilled Beef Tagliata to their signature Rosemary Olive Oil Cakes, Osteria Mozza’s is a menu Angelenos can recite by heart: the greatest hits.

In 2014, Nancy received the highest honor given by the James Beard Foundation, the award for “Outstanding Chef.” That year, she was listed as one of the Most Innovative Women in Food and Drink by both Fortune and Food & Wine Magazines. In 2017, Nancy was profiled in an episode of Netflix’s award-winning docu-series Chef’s Table. Silverton also founded the world-renowned La Brea Bakery as well as Campanile Restaurant, an institution that Angelenos cherished for decades. 

Silverton is the author of eight cookbooks including Desserts (1986), Breads from the La Brea Bakery (1996), Pastries from the La Brea Bakery (2000), Nancy Silverton’s Sandwich Book (2005), Twist of the Wrist (2007) and the Mozza Cookbook (2011).

  • Valid for up to 16 people.
  • Experience will take place on a mutually agreed upon date valid from March 20, 2023 to February 20, 2024
  • Participants must be at least 18 years old
  • All guests will receive a signed cookbook
  • The meal cost, wine, and gratuity are included
  • Based upon a mutually agreed upon date
  • Item cannot be resold or transferred
Thanks to: Nancy Silverton, Osteria Mozza, and Billy & Sharon Harris

Value: Priceless


Your group of 12 will immerse yourselves for an entire week on this incredible island escape in Cepaka! Bali is a living postcard, an Indonesian paradise that feels like a fantasy.  From its immaculate, elegant interior to the extraordinary service, this award-winning boutique villa takes the 5-star hotel experience to the next level. The villa offers everything you would expect from the world’s finest hotels, with the bonus of privacy and exclusivity. It’s perfect for families or friends on holiday together.
The 12 of you will be accommodated in 5 king pool-side suites and the 6th in an outdoor leisure pavilion. There are 6 en-suite bathrooms, complete with tropical open-air showers.
The staff-to-guest ratio is amazing and the customer service philosophy is benchmarked against the most exclusive boutique chains in the world. The accommodations are lavish, the cuisine is decadent and the service is exceptional. This is truly an escape of distinction—exclusive, sophisticated, and nothing short of magical.
Included in the package:
  • Pre-arrival guest preference and booking/planning service
  • Airport transfers in two, 7-seater chauffeured vehicles
  • Concierge service during the stay to arrange all bookings, tours, cruises, etc.
  • A comprehensive villa staff of 14 includes chefs and spa therapists*
  • Evening canapes on your first night
  • Daily full breakfasts (a la carte); Other meals are charged at cost of ingredients
  • Unlimited bottled water in rooms and dining areas
  • All day imported teas and Bali’s famous local coffee
  • Bespoke natural bathroom products
  • Room service twice daily including turn downs during dinner
  • Laundry and pressing service
  • Driver/tour guide for up to 10 hours a day
Restrictions: Available for bookings year-round, except for the following premium timeframes: Week of Easter, July & August, December 15-January 15. To book an available week during any of the above-mentioned timeframes, an additional US $1,300 surcharge will apply. Bookings are based on availability of accommodations and must be redeemed by March 19, 2024. Cost of food and ingredients to prepare all non-included meals and fuel used for chauffeured vehicles during the stay are not included. *Fees for in-house yoga and spa treatments are not included. Fuel fees for airport transfers are not included. A mandatory gratuity of US $550. Airfare is not included. Mandatory service tax of USD $643.75 (USD $720 in peak periods). Mandatory government tax of USD $167.50/day (USD $187/day peak periods).
Value: Priceless


What’s better than spending a week in Tuscany? Spending a week in Tuscany for a good cause with good friends. Your group of 10 will experience a luxury getaway in the postcard-perfect Cortona, in a villa among the vineyards. Majestic castles, Italian architecture, fabulous food, and fine wine - all await you in Tuscany! For seven days and nights, experience the heart of Italy in Tuscany’s soft rolling hills, lines of cypress trees, and tidy olive groves surrounding the ancient walled city of Cortona. Overlooking the enchanting landscape of the Valdichiana Valley and Lake Trasimeno, noble Cortona’s history goes back centuries as an important Etruscan center, Roman settlement, and medieval town. Magnificently positioned on a hill between the Chianti region and Umbrian valleys, Cortona is a strategic starting point for day trips to explore nearby areas on your own.
While here, you will stay in a beautiful, recently restored original stone villa that offers you complete luxury and privacy. The five queen bedrooms with ensuite bathrooms comfortably sleep 10. And to take this to the next level, a private chef will prepare breakfast and spectacular three-course dinners daily, highlighting traditional Tuscan flavors. Relax in the private swimming pool and spacious garden or fire up the stone pizza oven in the barbecue area for an al fresco lunch. Your villa’s spectacular location provides amazing views as well as easy access to Cortona where you can explore the town’s historic monuments, fascinating shops, and tempting restaurants.  
And to make this trip remarkable, your adventure includes a wine-making workshop in a traditional winery. Here you will taste single-variety wines from the vats and barrels located in their cellar. Under the guidance of the cellar master, each person in your group will mix base wines to create a brand-new blend, and then vote to choose the best one to bottle. You will also personalize your own labels to go on your bottles of the selected new wine – for a total of 60 bottles of wine (6 bottles for each). The winery will age the bottles for one month before you ship them back to the States. After this incredible workshop, all of you will enjoy a traditional Tuscan lunch in the charming dining room while tasting wines from the winery.
Summary of included services:
  • Seven (7) nights and seven (7) days stay (from Saturday to Saturday) for ten people in a Tuscan Villa
  • Arrival day welcome drink and orientation
  • Breakfast and dinner prepared each day by a private cook (groceries included except alcohol)
  • Full-day winemaking school with tastings and lunch at a winery
  • Blend your own 60 bottles of wine with custom labels
  • Housekeeping every day
  • One mid-week change of linen and towels
  • Heating and electricity, phone, internet, and final cleaning
  • A member of staff will always be at disposal before and during stays for trip details, preparation, and arranging free time for extra activities and services
Restrictions: One-week stay at one of four Tuscan villas from Saturday to Saturday for a maximum of ten guests. Arrivals take place between 3:30 PM and 7:00 PM. Departure by 09.30 AM. The pool is open from April 1 – October 30. Bookings are based on the availability of accommodations and must be redeemed by March 19, 2024. You are encouraged to book as soon as possible after the auction.
Value: Priceless