Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Bring home a striking work by internationally acclaimed Tlingit artist Preston Singletary, an artist who has redefined the boundaries of contemporary Indigenous art.

This luminous cast glass salmon, displayed on a custom metal stand, is more than a sculpture-it's a powerful expression of cultural identity, resilience, and storytelling. Singletary is known for merging traditional Tlingit formline design with modern glassblowing techniques, creating work that is both deeply rooted and unmistakably contemporary.

Inspired by generations of strong Tlingit women in his family, Singletary's work reflects a profound connection to heritage while challenging expectations of what Indigenous art can be. By using glass, an unconventional medium in Native art-he expands the narrative, affirming that Indigenous cultures are dynamic, evolving, and present.

Perfect for collectors and art lovers alike, this piece brings both visual impact and a meaningful story into any space.

Details:

• Open edition cast glass salmon (2021)
  
• Custom metal stand included
  
• Dimensions: 5" x 14" x 1"
  
  An opportunity to own a piece by one of the most influential voices in contemporary Indigenous art.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Wake up to golden light over the Tuscan hills, wander to the village cafe for espresso, and end your evenings with wine on the terrace as the sun sets over Siena in the distance.

Nestled in the storybook village of Trequanda, La Casa dei Fiordalisi is a beautifully restored 13th-century home that offers an experience few travelers ever find-a private residence built into the ancient city walls, where history, comfort, and understated luxury meet.

Designed for gathering, this exceptional property includes two private dwellings:
La Casa, a four-bedroom main house set into the historic wall, and La Casetta, a charming one-bedroom carriage house. Each offers its own living space, kitchen, and fireplace-creating the perfect balance of shared time and personal retreat.

With space for up to 10 adults, this is an ideal setting for multiple couples or families traveling together. Spend your days stretched out by the pool, exploring nearby vineyards and hill towns, or simply enjoying long meals and conversation across terraces overlooking the Tuscan countryside.

From here, some of Italy's most celebrated wine regions-Chianti, Montepulciano, and Montalcino-are within easy reach.

This is Tuscany as it's meant to be experienced: relaxed, beautiful, and the kind of trip that only gets better when shared.

Details:

• One-week stay (6 nights / 7 days) in Trequanda, Tuscany
• Two dwellings with 5 bedrooms in total
• Accommodates up to 10 guests
• Private garden, terraces, and swimming pool
• Multiple living areas, fireplaces, and full kitchens
• Dates subject to availability; expires November 30, 2027
• Not available December-February
• 2026 stays: Saturday-Saturday | 2027 stays: Monday-Monday

Gather your favorite people and make this the trip you'll talk about for years.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Breathe in crisp mountain air, watch the Yellowstone River flow just beyond your door, and experience the wild beauty of Montana, without giving up an ounce of comfort.

Your three-night stay at Sage Lodge, a Michelin Key-awarded retreat, offers a rare blend of rugged landscape and refined luxury, just 35 minutes from Yellowstone National Park.

You and your guests will stay in a private Ranch House, more than 2,700 square feet of beautifully designed space featuring two Double King rooms and two King Suites. It's the perfect setting for couples or friends traveling together, with generous space to gather and unwind.

Spend your days fly fishing, hiking, biking, or exploring Yellowstone itself. Then return to evenings of warmth and ease-whether that's relaxing at the spa, enjoying the lodge's acclaimed dining, or simply taking in the quiet of the surrounding landscape.

Your stay also includes a chef-curated dinner for eight, bringing everyone together for an unforgettable shared experience.

For those who love adventure-but prefer to do it well, this is the ultimate Montana escape.

Details:

• Three-night stay at Sage Lodge (Montana)
• Private Ranch House (4 bedrooms; ideal for 4 couples)
• Chef-curated dinner for eight included (excluding alcohol & gratuity)
• Access to spa, dining, and on-site activities
• Subject to availability; blackout dates and holidays excluded
• Expires May 2, 2027
  
  Adventure, elevated, just outside Yellowstone.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Step into pura vida at its most elevated-where cliffside views meet private plunge pools and the ocean stretches endlessly below you.

This five-night escape for two includes a stay at the award-winning Casa Chameleon at Las Catalinas, an adults-only luxury retreat perched above Costa Rica's Guanacaste coast. Each of the resort's private villas is designed for total immersion in the landscape, featuring sweeping ocean views and a personal saltwater plunge pool made for slow mornings and golden sunsets.

Set within the walkable, charming town of Las Catalinas, you'll have effortless access to adventure and relaxation alike-snorkeling, paddleboarding, surfing, hiking, or simply staying in and enjoying in-villa wellness treatments surrounded by nature.

To begin your journey in comfort and style, this package also includes two round-trip first-class tickets on Alaska Airlines between Seattle-Tacoma International Airport and Liberia, Costa Rica, just a short drive from paradise.

This is the rare kind of getaway where everything slows down the moment you arrive.

Details:

• Five-night stay for 2 guests at Casa Chameleon, Las Catalinas
• Adults-only luxury resort with private villa + plunge pool
• Located on Costa Rica's Guanacaste coast
• Two round-trip first-class Alaska Airlines tickets (SEA-LIR)
• Subject to availability; resort restrictions apply
• Airline vouchers must be ticketed by April 2, 2027
• No blackout dates on airfare

Cliffside luxury, ocean views, and the kind of escape you don't forget.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Wake to the sound of waves just steps from your door, where the Pacific stretches endlessly beyond your lanai and each day unfolds at the pace of island life.

This seven-day, six-night escape for four guests includes an oceanfront stay in Kona on Hawaii's Big Island, paired with four coach-class Alaska Airlines tickets to get you there.

Your home is a beautifully renovated three-bedroom, two-bath Hawaiian residence set directly on Kahaluu Bay-one of the island's most iconic coastal locations. With 185 feet of beachfront and unobstructed ocean views, this is island living at its most immersive.
Spend your days swimming, snorkeling, surfing at nearby breaks, or simply relaxing in the sun from your private lanai and garden patio. Just beyond your doorstep, explore volcanic landscapes, lush hiking trails, and the dramatic beauty of Volcanoes National Park.
Evenings are for slowing down and watching the sky shift over the Pacific and falling asleep to the rhythm of the waves.

Details:

• Seven-day, six-night stay in Kona, Big Island for four guests
• Three-bedroom, two-bath oceanfront home at Kahaluu Bay
• Direct beachfront setting with expansive Pacific views
• Four coach-class Alaska Airlines tickets included
• Travel valid May 15-Nov 15, 2026 or 2027
• Subject to availability; mutually agreed dates required
• Airline vouchers must be ticketed by April 2, 2027
• No blackout dates (airfare)
  

Oceanfront living, island adventure, and the Big Island at your doorstep.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

You've heard about New Zealand-one of the most breathtaking and welcoming places on earth, where sweeping mountains, braided river valleys, and vast open landscapes feel almost unreal in their scale and beauty.

This seven-night escape offers a rare stay in IslandWood founder, Debbi Brainerd's private stone cottage at Wyuna Preserve, a working sheep farm set above the small alpine village of Glenorchy.

Surrounded by a few acres within the larger preserve, this two-bedroom home is a true retreat into high-country New Zealand-quiet, remote, and deeply connected to the land.

From here, you are perfectly positioned to explore some of the most iconic outdoor experiences in the world. Hike portions of the Milford or Routeburn Tracks, fly fish pristine rivers, ride horses through open valleys, or kayak and jet boat through dramatic alpine terrain. The landscapes of nearby Mount Aspiring National Park are so striking they've served as filming locations for The Lord of the Rings, The Hobbit, and Narnia.

This is a place where time stretches, silence feels expansive, and every view looks like it belongs on a postcard.

Details:

• Seven-night stay in Debbi Brainerd's stone cottage (New Zealand)
  
• Two-bedroom private home on working sheep farm (Wyuna Preserve)
  
• Located above Glenorchy, near Mount Aspiring National Park
  
• Ideal base for hiking, fishing, horseback riding, kayaking, and jet boating
  
• Valid through end of 2028
  
• Mutually agreeable dates; to be coordinated prior to Dinner in the Woods 2027.
  
• A rare chance to experience New Zealand at its most raw, beautiful, and unforgettable.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Spend a rare, intimate evening with #1 bestselling author Kristin Hannah in conversation with IslandWood Founder Debbi Brainerd at her Bainbridge Island home on Blakely Point.

This special gathering brings together you and a small group of guests for an unforgettable evening of conversation, connection, and storytelling. Enjoy appetizers and drinks as Kristin shares insights into her writing, her creative process, and the inspiration behind her unforgettable novels.

Kristin Hannah is one of the most widely read authors of our time, known for powerful, emotionally resonant stories including The Nightingale and The Women. Her novels have become global bestsellers and award winners and continue to shape contemporary historical fiction for millions of readers worldwide.

This is a rare opportunity to spend meaningful time with a master storyteller in an intimate setting-far from the stage, and close enough for real conversation.

Details:

• Private evening with Kristin Hannah and IslandWood Founder Debbi Brainerd
  
• Hosted at Debbi Brainerd's private Bainbridge Island residence (Blakely Point)
  
• Includes appetizers and drinks
  
• Group of up to 20 guests
  
• Mutually agreed-upon date
  
• Must be scheduled before end of 2027
  
  An unforgettable evening of storytelling, conversation, and connection.
  

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Indulge in an unforgettable evening of fine dining and rare wines, hosted at IslandWood for a group of twelve guests.
This exclusive farm-to-table dinner is thoughtfully prepared by Chef Jim White and his culinary team, featuring a seasonal menu built around the freshest locally sourced ingredients-crafted specifically to complement an exceptional selection of rare and remarkable wines.
The evening draws from the private cellar of former IslandWood Board Member and longtime supporter Fred Kleisner, offering a curated tasting experience rarely available outside of a private collection. Under the guidance of a professional sommelier, guests will explore each pairing, discovering the nuance, depth, and story behind every pour.
This is more than a dinner-it is a guided journey through flavor, craftsmanship, and connection, shared around the table with friends and fellow guests.

Details:

• Private wine dinner for 12 guests at IslandWood
  
• Multi-course seasonal farm-to-table menu by Chef Jim White and team
  
• Rare wine pairings from private cellar collection
• Guided tasting experience with professional sommelier
• Must be 21+
• Mutually agreeable date, excluding Saturdays June-September
• Expires May 3, 2027

A rare evening of extraordinary wines, exceptional food, and unforgettable company.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Sail through some of Europe's most captivating coastal landscapes on a 10-night luxury voyage from Bordeaux to Lisbon aboard the exclusively chartered Le Laperouse.

This thoughtfully paced journey for two blends elegant travel with immersive cultural discovery-moving through the Atlantic coast of France, the vibrant ports of northern Spain, and into the rich maritime traditions of Portugal.

Each day brings a new horizon: UNESCO World Heritage sites, storied seaside villages, world-class museums, and guided excursions led by expert local teams who bring each destination to life in meaningful detail. From lively harbor cities to quiet historic towns, this is Europe seen from a rare and elevated perspective.

Aboard Le Laperouse, a 5-star small ship designed for intimacy and comfort, guests enjoy beautifully appointed accommodations, exceptional service, and chef-prepared cuisine throughout the voyage.

This is travel at its most seamless-where every detail is handled, and every day offers something unforgettable.

Details:

• 10-night luxury cruise for 2 guests (Bordeaux to Lisbon)
• Aboard the exclusively chartered 5-star Le Laperouse.
• Departing October 1-12, 2026
• All onboard meals included: breakfast, lunch, dinner, with beverages
• Guided small-group excursions and cultural tours at select ports
• UNESCO sites, historic cities, and curated experiences throughout
• Welcome and farewell receptions included

A rare chance to experience the European coast in effortless, elevated style.

Live Auction Items (100s) will be available for in-person bidding on Saturday, May 2, during the live broadcast program. Click Here to request a proxy bid!

Join two of IslandWood's most cherished personalities-Founder Debbi Brainerd and Chef Jim White-for an unforgettable evening of cooking, conversation, and connection in a private Bainbridge Island home.

This is a rare chance to step inside Debbi's home on Blakely Point for a warm, hands-on cooking experience led by Debbi and Chef Jim-hosts known and loved across the IslandWood community for creating gatherings that feel both joyful and deeply welcoming.
Together with up to eight guests, you'll prepare a seasonal multi-course menu side by side, learning approachable techniques and recipes in a relaxed, interactive kitchen setting.

The evening flows into a shared four-course dinner in the greenhouse dining room, complete with libations, easy conversation, and the kind of hospitality that makes you want to stay at the table a little longer.

Details:

• Private cooking class and dinner for up to 8 guests
  
• Hosted by IslandWood Founder Debbi Brainerd and Chef Jim White
  
• Hands-on seasonal cooking experience
  
• Four-course dinner in greenhouse dining room
  
• Location: private home on Blakely Point, Bainbridge Island
  
• Mutually agreed-upon date
  
  An evening of cooking, connection, and the warmth IslandWood is known for.