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.
Check out the auction video and details below!
Check out the auction video and details below!
4-NIGHT FAMILY STAY AT FOUR SEASONS RESORT MAUI WITH OCEAN VIEW FOR 2 ADULTS & 2 KIDS
Escape to paradise with an incredible 4-night family getaway in an ocean view room for a family of four to the Four Seasons Resort Maui. Nestled on 15 lush acres along the breathtaking Wailea Coast. This exclusive experience invites you to relax and unwind at a world-renowned oceanfront property celebrated for its refined luxury, impeccable service, and harmony with the island’s natural beauty. Guests enjoy complimentary amenities that are rare among Hawaiian resorts—including 3 stunning saltwater pools, access to a globally acclaimed spa and wellness center, and exceptional service throughout your stay. This dreamy island escape also includes one Luxe Travel Essentials Set from ANINE BING, including a signature Large Rio Tote. Thoughtfully curated to elevate your vacation wardrobe, Anine Bing blends Scandinavian simplicity with American energy, offering modern essentials for women seeking timeless yet confident style.
Savor world-class cuisine at 3 of Hawaii’s most celebrated restaurants: Spago Maui, Ferraro’s Bar e Ristorante, and DUO Steak and Seafood, all set against the backdrop of Maui’s iconic sunsets. Recognized as a TripAdvisor Certificate of Excellence Hall of Famer, this resort promises a once-in-a-lifetime escape your family will never forget.
Start bidding now and say aloha to luxury, relaxation, and island magic!
Restrictions: Redemption is based on Four Seasons Resort Maui availability. Certificate valid through April 26, 2026. Reservations are required and can only be made 60 days or less prior to date of arrival. Blackout Dates: 2025: Apr 23-May 2, Jul 5, Aug 9, Nov 26, 27, Dec 20-Jan 3, 2026 2026: Feb 24-28, Mar 14 & 21. Additional blackout dates may occur. Expired Certificates will not be honored, expiration dates will not be extended, and they will not be replaced if lost or stolen. This certificate is non-transferable, non-redeemable for cash, not valid with any other promotion and cannot be resold.
Value: Priceless
Thanks To: Talin & Scott Tenley, Anine & Nicolai Bing, Julie Friedman, The Friedman Group, and Four Seasons Resort Maui
SMASH BURGERS & GOOD TIMES: THE ULTIMATE BACKYARD FEAST FOR 100 BY HEAVY HANDED
Win the ultimate backyard party for 100, catered by LA’s hottest burger spot—Heavy Handed.
Get ready to throw an unforgettable backyard bash, complete with sizzling smash burgers, golden fries, incredible sides, wine, and the unmistakable vibe of one of Los Angeles’ most buzzed-about culinary sensations: Heavy Handed.
What began as a pandemic pop-up in a Mar Vista driveway has exploded into a citywide phenomenon, with devoted fans flocking to their Santa Monica, Studio City, and Silver Lake locations. Now, they’re bringing the flavor to you—with a 3 hour private event for 100 guests, right in your own backyard.
At this delicious gathering, you and your friends will feast on signature short rib smash burgers, perfectly seared with crispy, lacy edges and melty American cheese, all tucked into plush potato rolls. Pair them with house-made pickles, beef-tallow fries, and a variety of mouthwatering sides. And don’t forget the iconic Thousand Island-style sauce that food lovers across LA can’t stop raving about. The event will also include wine to complement the bold, savory flavors and enhance your guests’ overall dining experience.
To finish things off in style, Valerie Confections—a cherished LA institution—will serve a stunning array of handcrafted pies. Their buttery, flaky crusts and creative seasonal fillings are the perfect finale to this indulgent spread. From fresh fruit classics to inventive treats like the famous Chocolate Caramel Nut Tart, these small-batch pies balance comfort with culinary sophistication, adding a sweet and memorable final note to the feast.
Whether you're planning a summer celebration, fall festivity, or just looking for an unforgettable excuse to bring your favorite people together, this party promises bold flavors, good vibes, and unforgettable memories.
Value: Priceless
Restrictions: Mutually agreed upon date. 3-hour Heavy Handed experience.
Thanks to: Heavy Handed, Valerie Confections, Billy & Sharon Harris
LUXURY IN PARADISE – 4-NIGHT ESCAPE TO FOUR SEASONS TAMARINDO, MEXICO FOR 4 ADULTS AND 4 CHILDREN
Discover the magic of Mexico’s pristine Pacific coastline with a 4-night stay in two Cliffside Oceanview One-Bedroom Suites with Private Pools at the Four Seasons Resort Tamarindo, Mexico—an exclusive, ultra-luxurious retreat perched above the ocean in a 3,000-acre private nature reserve. This exclusive package accommodates up to four adults and four children, making it the perfect tropical escape for families or friends seeking a blend of adventure and relaxation in a secluded, world-class setting.
Each Cliffside oceanview one-bedroom suite features a private 43-foot infinity pool, outdoor shower and hammock, a large furnished terrace, and floor-to-ceiling windows with sweeping ocean views from every room. Suites also include a well-stocked private bar, a spacious bathroom with walk-in closet access, and handcrafted touches that blend luxury with nature. Enjoy full access to the resort’s exceptional amenities, including holistic spa experiences that restore balance through treatments rooted in local healing traditions and three world-class restaurants—including Coyul by renowned Chef Elena Reygadas. This unforgettable tropical getaway also includes Luxe Travel Essentials Sets from ANINE BING, featuring two signature Large Rio Totes.
Golf enthusiasts can tee off at the spectacular El Tamarindo Golf Course, an 18-hole masterpiece by David Fleming that winds through jungle, cliffs, and oceanfront fairways. For those craving adventure, the resort offers nature-focused activities such as guided hikes, boat excursions, and wildlife encounters that immerse guests in the region’s rich biodiversity. And when it’s time to unwind, guests can enjoy secluded beaches, tiered infinity pools, and serene wellness spaces. Whether you're seeking relaxation, outdoor exploration, or gourmet indulgence, this unforgettable getaway truly offers something for every traveler.
Restrictions: This package includes two Cliffside Ocean View Suites with Infinity Pool for four nights for up to two adults and two kids in each suite. Certificate valid through April 30, 2026. Redemption is based on availability at Four Seasons Resort Tamarindo; additional holidays or blackout dates may apply. Expired certificates will not be honored, expiration dates will not be extended, and they will not be replaced if lost or stolen. The certificate is non-transferable, non-redeemable for cash, not valid with any other promotion, and cannot be resold.
Value: Priceless
Thanks To: Talin & Scott Tenley, Anine & Nicolai Bing, Julie Friedman, The Friedman Group, and Four Seasons Resort Tamarindo
A NIGHT TO REMEMBER: CHEF NANCY SILVERTON AT YOUR HOME FOR 12
Host the dinner party of a lifetime—right in the comfort of your own home. Renowned James Beard Award-winning Chef Nancy Silverton, the visionary behind Osteria Mozza, Pizzeria Mozza, and chi SPACCA, will personally design and cook an extraordinary meal for you and 11 guests.
Your party of 12 will savor a stunning multi-course meal showcasing Nancy’s signature Italian and Mediterranean flavors, complemented by fresh, seasonal creations. Each dish will be beautifully paired with exceptional wines from Fine Disregard Wine Co., further elevating the experience.
This intimate, one-of-a-kind culinary celebration will take place in the fall of 2025 and offers a rare opportunity to experience the magic of Nancy Silverton—up close and in your own dining room. Each guest will also receive a special signed cookbook.
Chef Nancy’s impact on the culinary world is far-reaching. A recipient of the James Beard Foundation’s “Outstanding Chef” award, she has been named one of the Most Innovative Women in Food and Drink by Fortune and Food & Wine, featured in Netflix’s Chef’s Table, and authored several acclaimed cookbooks.
Wine pairings for the evening will be provided by Fine Disregard Wine Co., a Napa Valley producer led by a passionate two-person team devoted to crafting wines of purity and character. Sourcing from distinctive vineyard sites and using sustainable farming practices, they embrace a minimal-intervention philosophy—harvesting early, fermenting with native yeast, and aging in seasoned barrels. The result: expressive, uniquely Californian wines with elegance and soul.
This is your chance to enjoy an evening of remarkable food, wine, and connection with one of America’s most celebrated chefs—all in the intimate setting of your own home.
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Valid for up to 12 guests
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Experience will take place on a mutually agreed-upon date in the fall of 2025
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All guests will receive a signed cookbook
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Item is non-transferable and may not be resold
Value: Priceless
Thanks To: Nancy Silverton, Fine Disregard Wine Co., Mike Schieffer, Kara Maraden, Billy & Sharon Harris
ICELAND: LAND OF FIRE, ICE, AND PURE MAGIC – 5 NIGHTS FOR 8 GUESTS
Win an amazing trip of a lifetime to one of the coolest and wildest destinations on Earth—Iceland, a land of spectacular contrasts where unspoiled nature reigns supreme. Your group of 8 will enjoy 5 unforgettable nights in a stunning modern lodge that blends rustic charm with Icelandic tradition, set amidst dramatic hills and rugged peaks—yet conveniently close to Reykjavik and the famed Golden Circle. The lodge features four bedrooms, four bathrooms, expansive open-plan living and dining areas, and panoramic valley views through floor-to-ceiling windows. Step onto the covered terrace for al fresco dining or unwind in the outdoor hot tub as you gaze across the valley—and, during the right season, watch the Northern Lights dance overhead.
Often called the Land of Fire and Ice, Iceland is full of energy, mystery, and raw beauty, with everything from steaming volcanoes and black sand beaches to glowing glaciers and jagged fjords.
Your package includes a 3-hour private glacier hike on Sólheimajökull Glacier, a traditional Icelandic dinner prepared at your villa by local hosts, and full concierge service and travel assistance to help you plan every detail of your adventure. You’ll be close to some of Iceland’s most iconic landmarks—Thingvellir National Park, the Strokkur Geysir, Gullfoss Waterfall, and Kerid Crater—making it easy to explore the magic of the Golden Circle. In the south, embark on a breathtaking journey to the glacier, with sweeping views at every turn. From epic outdoor adventure to soul-stirring natural beauty, Iceland promises an experience that will capture your heart—and stay with you forever.
Restrictions: Bookings are handled on a first-come, first-served basis and are subject to availability. Blackout dates: Jul 15-Aug 15, 2025, Dec 20, 2025 through January 6, 2026. This package includes a 5-night stay for a maximum of 8 guests. It is highly recommended that winners book their stay as soon as possible or at the latest by May 26, 2025, and your stay must be completed by April 26, 2026. Please note that there is no refund for unattended or guest-canceled services. Airfare and excursion transportation are excluded.
Value: Priceless
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Contact specialevent@oakwoodschool.org for more information.
Oakwood School is a 501(c)3 nonprofit organization. All gifts are tax-deductible to the fullest extent allowed by law.