The Aloha Collection: Your Island, Your Adventure
Choose Your Paradise and Customize Your Unforgettable Hawaiian Escape
This Experience for 2 Includes:
- 4 nights at a menu of Outrigger Resorts – choose the islands and duration that inspire you most.
- Outrigger Waikiki Beach Resort – City View room
- Outrigger Kona Resort and Spa – Resort view
- Outrigger Kauai Beach Resort & Spa – Garden View room
- Outrigger Ka’anapali Beach Resort – Premium Garden View room
- Your choice of one experience from a curated selection of adventures
- Winspire booking & concierge service
Experience Hawaii your way with the freedom to choose – or divide your stay between – any of four enchanting islands: O‘ahu, Maui, Kaua‘i, or the Big Island of Hawai‘i. Each four-night getaway for two includes luxurious accommodations at an Outrigger Resort, and an adventure to explore the island. Dive into history at Pearl Harbor, watch the sunrise over Haleakalā, explore volcanic landscapes in Kona, or cruise through the cinematic beauty of Kaua‘i.
Whether you savor four serene nights in one paradise or split your stay between multiple islands for the adventure, every moment is curated for wonder, relaxation, and discovery. With Winspire’s expert booking and concierge service, your dream island-hopping Hawaiian escape begins exactly how you imagine it.
Oahu
Outrigger Reef Waikiki Beach Resort: Oceanfront Luxury with the Spirit of Aloha
Set directly on Waikiki Beach, the Outrigger Reef Waikiki Beach Resort is more than a place to stay – it’s a celebration of Hawaiian culture and coastal living. Newly reimagined with elegant island-inspired design, this oceanfront sanctuary offers everything you could dream of in a tropical getaway.
Wake each morning to the sound of waves and views of Diamond Head’s iconic silhouette. Enjoy breakfast by the water at Kani Ka Pila Grille, where live Hawaiian music drifts through the air each evening. Spend your days relaxing by the oceanfront pool and cabanas, indulging in a massage at the La`akea Spa, or stepping straight onto the golden sands for a dip in the Pacific.
The resort’s authentic sense of place sets it apart – from its Hawaiian art collection and welcoming cultural center to the warm hospitality that makes every guest feel like part of the ʻohana (family). With boutique shopping, world-class dining, and legendary Waikiki sunsets just steps away, the Outrigger Reef is the ultimate island retreat.
Your Choice of Island Adventure
Select from two immersive guided tours, each offering a unique perspective of Oahu’s beauty and heritage.
- Oahu Grand Circle Tour
Experience the full grandeur of Oahu on a full-day circle island tour. Travel through lush rainforests, visit sacred sites, and stop at breathtaking viewpoints like Nuʻuanu Pali Lookout. Discover hidden coves, pineapple fields, and the famous North Shore surf beaches, where the island’s natural splendor comes alive. - Pearl Harbor, Memorial & City Tour
For a deeper look at Hawaii’s story, journey through history at Pearl Harbor. Visit the USS Arizona Memorial, a solemn tribute to courage and sacrifice, before touring Honolulu’s cultural heart – from the royal ʻIolani Palace to the majestic King Kamehameha statue.
Maui
Outrigger Kāʻanapali Beach Resort: Island Luxury with a Spirit of Aloha
Set along one of Maui’s most iconic stretches of shoreline, Kāʻanapali Beach Resort is a paradise where turquoise waters meet golden sands and the warmth of aloha fills the air. Your Premium Garden View Room offers a peaceful haven framed by swaying palms and lush tropical foliage, just steps from the beach and the resort’s vibrant heart.
Each morning begins with the sound of gentle waves and the scent of plumeria drifting through the air. Spend your days basking by lagoon-style pools, snorkeling with sea turtles at nearby Black Rock, or relaxing in a private cabana with a cool drink in hand. For the adventurous, paddleboarding, catamaran sails, and guided ocean excursions await.
Embrace island life with cultural experiences like lei-making, hula lessons, and evening torch-lighting ceremonies. Indulge in a massage using island botanicals at the full-service spa, then savor fresh island cuisine at one of the resort’s acclaimed restaurants. As the sun sets in a blaze of color, the beach transforms into a front-row seat to Maui’s legendary twilight.
With boutique shops, oceanfront dining, and easy access to nearby Lahaina, Kāʻanapali Beach offers the perfect blend of luxury, culture, and relaxation.
Your Choice of Island Adventure
Select from four unforgettable guided experiences – each capturing the essence of Maui’s beauty and spirit.
- Haleakalā Sunrise Tour with Breakfast
Journey to the summit of Maui’s majestic volcano before dawn and watch as the sun rises above the clouds, painting the sky in hues of gold and pink. This once-in-a-lifetime experience is followed by a delicious island-style breakfast to start your day. - Haleakalā Sunset Tour with Dinner
For those who prefer evening magic, ascend Haleakalā as the sun dips below the horizon, bathing the crater in fiery colors. Afterward, enjoy a leisurely dinner at a local restaurant, reflecting on the day’s beauty beneath a canopy of stars.
- Road to Hāna Adventure
Discover the wild side of Maui on one of the world’s most scenic drives. Wind through rainforests and along ocean cliffs, stopping to explore waterfalls, black-sand beaches, and charming roadside stands filled with local fruit and crafts.
- Best of Maui Food Tour
Savor Maui’s flavors on a guided culinary journey across the island. Visit local farms, sample artisan treats, and indulge in regional dishes that blend Hawaii’s diverse cultural influences – a feast for both palate and soul.
Kona
Outrigger Kona Resort & Spa: Oceanfront Serenity Meets Hawaiian Spirit
Perched dramatically atop lava rock cliffs overlooking Keauhou Bay, the Outrigger Kona Resort & Spa captures the raw beauty and cultural heart of Hawai‘i Island. With breathtaking ocean views, warm island hospitality, and modern amenities, this seaside sanctuary is the perfect place to unwind and reconnect.
Each morning begins with the rhythm of waves against the shore and coffee grown on the volcanic slopes of Kona. Spend your days lounging by the multi-level oceanfront pool, relaxing in the spa, or exploring the nearby tide pools and walking trails. For the adventurous, snorkeling excursions, manta ray night dives, and outrigger canoe rides await just steps from the resort.
As the sun sets, the cliffs glow with golden light and torches flicker to life – a nightly reminder of the island’s natural drama and deep-rooted traditions. With its blend of comfort, culture, and oceanfront wonder, the Outrigger Kona offers an experience that feels authentically Hawaiian.
Your Choice of Island Adventure
Select from two experiences to help bring Kona to life:
- Volcano Adventure Tour
Embark on an unforgettable journey through Hawai‘i Volcanoes National Park, where the island’s fiery heart still beats beneath your feet. Discover steam vents, lava fields, and the immense Kīlauea Caldera as expert guides share stories of Pele, the Hawaiian goddess of fire. Explore the lush landscapes that surround this otherworldly terrain, stop for scenic viewpoints, and enjoy a delicious local-style lunch along the way. It’s a day that captures the raw power and beauty of Hawai‘i in motion.
- Outrigger Kona Lūʻau: Feast & Fire
Experience the magic of a Hawaiian evening under the stars at the Outrigger Kona’s signature Lūʻau. This unforgettable night begins with a traditional lei greeting and continues with cultural demonstrations, live island music, and breathtaking hula performances. As the fire knife dancers ignite the stage, savor a feast of Hawaiian favorites – slow-roasted kalua pork, fresh island fish, tropical fruits, and more. With the Pacific as your backdrop and tiki torches flickering in the breeze, it’s a celebration of aloha you’ll never forget.
Kaua‘i
Outrigger Kaua‘i Beach Resort & Spa: Oceanfront Tranquility on the Garden Isle
Nestled along a golden stretch of shoreline near Līhu‘e, the Outrigger Kaua‘i Beach Resort & Spa is a tropical haven where lush gardens meet the Pacific. Surrounded by swaying palms, cascading waterfalls, and the gentle rhythm of the ocean, this retreat embodies the beauty and serenity that make Kaua‘i unforgettable.
Your stay in a spacious island-inspired room offers private lanai views of vibrant tropical gardens and soothing trade winds. Spend your days floating in one of four sparkling pools – including a sand-bottom lagoon – or strolling the beach as the sun warms the horizon.
Rejuvenate at the oceanfront spa, sip Mai Tais by the pool, and indulge in fresh island cuisine featuring local seafood and produce. Every evening, the sunset paints the sky in hues of gold and rose – the perfect backdrop for a peaceful escape into island time.
With its authentic sense of aloha, lush surroundings, and easy access to both the North Shore and South Shore, the Outrigger Kaua‘i Beach Resort is the ultimate gateway to exploring the Garden Isle.
Your Choice of Island Adventure
Choose from three guided adventures during your stay:
- Kaua‘i Movie Sites Tour
Step into the scenes of cinematic legend on this guided journey through Kaua‘i’s most famous filming locations. From the cliffs of “Jurassic Park” to the beaches of “South Pacific” and “Pirates of the Caribbean,” you’ll experience the island’s breathtaking landscapes as Hollywood’s lens once did. Along the way, your expert guide will share behind-the-scenes stories that bring the island’s movie magic to life.
- Waimea Canyon & Fern Grotto Tour
Discover the natural wonders of Kaua‘i on a day of awe-inspiring sights. Begin with the “Grand Canyon of the Pacific”, Waimea Canyon — a kaleidoscope of red, green, and gold cliffs stretching for miles. Then journey to the Fern Grotto, a lush, natural amphitheater draped in hanging ferns and serenaded by gentle island melodies. This tour is a celebration of Kaua‘i’s untamed beauty and tranquil spirit.
- Kōke‘e Adventure
For those who crave exploration, journey deep into the island’s heart on a guided Kōke‘e Adventure. Venture through cool mountain forests, take in sweeping views from Kalalau Lookout, and learn about the island’s rare native flora and fauna. With its combination of rugged trails and panoramic vistas, this experience reveals a side of Kaua‘i few ever see — wild, remote, and soul-stirringly beautiful.
Why This Experience Captivates Donors and Closes Bids
- Freedom to Choose Your Paradise: This isn’t a one-size-fits-all getaway – it’s a tailor-made Hawaiian escape. Donors can choose the island that calls to their spirit – or mix and match multiple islands for the ultimate adventure. From O‘ahu’s vibrant energy to Maui’s golden sunsets, Kona’s volcanic drama to Kaua‘i’s lush serenity, every choice feels like the right one.
- Luxury Meets Authentic Aloha: Each Outrigger Resort embodies the heart of Hawai‘i – where contemporary comfort blends seamlessly with local culture. Whether waking to the sound of waves or dining beneath a sky of stars, every moment feels personal, warm, and unforgettable.
- Adventures for Every Traveler: From snorkeling beside sea turtles and witnessing the sunrise over Haleakalā to exploring volcanoes or attending an oceanfront lūʻau, donors can handpick their perfect experience. This flexibility creates instant emotional resonance – everyone dreams of their own Hawai‘i.
- High Perceived Value & Instant Appeal: With four nights of resort accommodations and curated adventure options, this package offers both luxury and choice – a combination that consistently drives competitive bidding and donor excitement.
- Effortless Planning with Concierge Support: Winspire’s expert concierge handles every detail – from bookings and timing to special requests – ensuring donors enjoy the ease of a fully customized Hawaiian getaway from the moment they say aloha.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major US holidays, Ironman, and other major local events. Additional dates may apply.
Choose Your Paradise and Customize Your Unforgettable Hawaiian Escape
This Experience for 2 Includes:
- 6 nights at a menu of Outrigger Resorts – choose the islands and duration that inspire you most.
- Outrigger Waikiki Beach Resort – City View room
- Outrigger Kona Resort and Spa – Resort view
- Outrigger Kauai Beach Resort & Spa – Garden View room
- Outrigger Ka’anapali Beach Resort – Premium Garden View room
- Your choice of two experiences from a curated selection of adventures
- Winspire booking & concierge service
Experience Hawaii your way with the freedom to choose – or divide your stay between – any of four enchanting islands: O‘ahu, Maui, Kaua‘i, or the Big Island of Hawai‘i. Each six-night getaway for two includes luxurious accommodations at an Outrigger Resort, and an adventure to explore the island. Dive into history at Pearl Harbor, watch the sunrise over Haleakalā, explore volcanic landscapes in Kona, or cruise through the cinematic beauty of Kaua‘i.
Whether you savor six serene nights in one paradise or split your stay between multiple islands for the adventure, every moment is curated for wonder, relaxation, and discovery. With Winspire’s expert booking and concierge service, your dream island-hopping Hawaiian escape begins exactly how you imagine it.
Oahu
Outrigger Reef Waikiki Beach Resort: Oceanfront Luxury with the Spirit of Aloha
Set directly on Waikiki Beach, the Outrigger Reef Waikiki Beach Resort is more than a place to stay – it’s a celebration of Hawaiian culture and coastal living. Newly reimagined with elegant island-inspired design, this oceanfront sanctuary offers everything you could dream of in a tropical getaway.
Wake each morning to the sound of waves and views of Diamond Head’s iconic silhouette. Enjoy breakfast by the water at Kani Ka Pila Grille, where live Hawaiian music drifts through the air each evening. Spend your days relaxing by the oceanfront pool and cabanas, indulging in a massage at the La`akea Spa, or stepping straight onto the golden sands for a dip in the Pacific.
The resort’s authentic sense of place sets it apart – from its Hawaiian art collection and welcoming cultural center to the warm hospitality that makes every guest feel like part of the ʻohana (family). With boutique shopping, world-class dining, and legendary Waikiki sunsets just steps away, the Outrigger Reef is the ultimate island retreat.
Your Choice of Island Adventure
Select from two immersive guided tours, each offering a unique perspective of Oahu’s beauty and heritage.
- Oahu Grand Circle Tour
Experience the full grandeur of Oahu on a full-day circle island tour. Travel through lush rainforests, visit sacred sites, and stop at breathtaking viewpoints like Nuʻuanu Pali Lookout. Discover hidden coves, pineapple fields, and the famous North Shore surf beaches, where the island’s natural splendor comes alive.
- Pearl Harbor, Memorial & City Tour
For a deeper look at Hawaii’s story, journey through history at Pearl Harbor. Visit the USS Arizona Memorial, a solemn tribute to courage and sacrifice, before touring Honolulu’s cultural heart – from the royal ʻIolani Palace to the majestic King Kamehameha statue.
Maui
Outrigger Kāʻanapali Beach Resort: Island Luxury with a Spirit of Aloha
Set along one of Maui’s most iconic stretches of shoreline, Kāʻanapali Beach Resort is a paradise where turquoise waters meet golden sands and the warmth of aloha fills the air. Your Premium Garden View Room offers a peaceful haven framed by swaying palms and lush tropical foliage, just steps from the beach and the resort’s vibrant heart.
Each morning begins with the sound of gentle waves and the scent of plumeria drifting through the air. Spend your days basking by lagoon-style pools, snorkeling with sea turtles at nearby Black Rock, or relaxing in a private cabana with a cool drink in hand. For the adventurous, paddleboarding, catamaran sails, and guided ocean excursions await.
Embrace island life with cultural experiences like lei-making, hula lessons, and evening torch-lighting ceremonies. Indulge in a massage using island botanicals at the full-service spa, then savor fresh island cuisine at one of the resort’s acclaimed restaurants. As the sun sets in a blaze of color, the beach transforms into a front-row seat to Maui’s legendary twilight.
With boutique shops, oceanfront dining, and easy access to nearby Lahaina, Kāʻanapali Beach offers the perfect blend of luxury, culture, and relaxation.
Your Choice of Island Adventure
Select from four unforgettable guided experiences – each capturing the essence of Maui’s beauty and spirit.
- Haleakalā Sunrise Tour with Breakfast
Journey to the summit of Maui’s majestic volcano before dawn and watch as the sun rises above the clouds, painting the sky in hues of gold and pink. This once-in-a-lifetime experience is followed by a delicious island-style breakfast to start your day.
- Haleakalā Sunset Tour with Dinner
For those who prefer evening magic, ascend Haleakalā as the sun dips below the horizon, bathing the crater in fiery colors. Afterward, enjoy a leisurely dinner at a local restaurant, reflecting on the day’s beauty beneath a canopy of stars.
- Road to Hāna Adventure
Discover the wild side of Maui on one of the world’s most scenic drives. Wind through rainforests and along ocean cliffs, stopping to explore waterfalls, black-sand beaches, and charming roadside stands filled with local fruit and crafts.
- Best of Maui Food Tour
Savor Maui’s flavors on a guided culinary journey across the island. Visit local farms, sample artisan treats, and indulge in regional dishes that blend Hawaii’s diverse cultural influences – a feast for both palate and soul.
Kona
Outrigger Kona Resort & Spa: Oceanfront Serenity Meets Hawaiian Spirit
Perched dramatically atop lava rock cliffs overlooking Keauhou Bay, the Outrigger Kona Resort & Spa captures the raw beauty and cultural heart of Hawai‘i Island. With breathtaking ocean views, warm island hospitality, and modern amenities, this seaside sanctuary is the perfect place to unwind and reconnect.
Each morning begins with the rhythm of waves against the shore and coffee grown on the volcanic slopes of Kona. Spend your days lounging by the multi-level oceanfront pool, relaxing in the spa, or exploring the nearby tide pools and walking trails. For the adventurous, snorkeling excursions, manta ray night dives, and outrigger canoe rides await just steps from the resort.
As the sun sets, the cliffs glow with golden light and torches flicker to life – a nightly reminder of the island’s natural drama and deep-rooted traditions. With its blend of comfort, culture, and oceanfront wonder, the Outrigger Kona offers an experience that feels authentically Hawaiian.
Your Choice of Island Adventure
Select from two experiences to help bring Kona to life:
- Volcano Adventure Tour
Embark on an unforgettable journey through Hawai‘i Volcanoes National Park, where the island’s fiery heart still beats beneath your feet. Discover steam vents, lava fields, and the immense Kīlauea Caldera as expert guides share stories of Pele, the Hawaiian goddess of fire. Explore the lush landscapes that surround this otherworldly terrain, stop for scenic viewpoints, and enjoy a delicious local-style lunch along the way. It’s a day that captures the raw power and beauty of Hawai‘i in motion.
- Outrigger Kona Lūʻau: Feast & Fire
Experience the magic of a Hawaiian evening under the stars at the Outrigger Kona’s signature Lūʻau. This unforgettable night begins with a traditional lei greeting and continues with cultural demonstrations, live island music, and breathtaking hula performances. As the fire knife dancers ignite the stage, savor a feast of Hawaiian favorites – slow-roasted kalua pork, fresh island fish, tropical fruits, and more. With the Pacific as your backdrop and tiki torches flickering in the breeze, it’s a celebration of aloha you’ll never forget.
Kaua‘i
Outrigger Kaua‘i Beach Resort & Spa: Oceanfront Tranquility on the Garden Isle
Nestled along a golden stretch of shoreline near Līhu‘e, the Outrigger Kaua‘i Beach Resort & Spa is a tropical haven where lush gardens meet the Pacific. Surrounded by swaying palms, cascading waterfalls, and the gentle rhythm of the ocean, this retreat embodies the beauty and serenity that make Kaua‘i unforgettable.
Your stay in a spacious island-inspired room offers private lanai views of vibrant tropical gardens and soothing trade winds. Spend your days floating in one of four sparkling pools – including a sand-bottom lagoon – or strolling the beach as the sun warms the horizon.
Rejuvenate at the oceanfront spa, sip Mai Tais by the pool, and indulge in fresh island cuisine featuring local seafood and produce. Every evening, the sunset paints the sky in hues of gold and rose – the perfect backdrop for a peaceful escape into island time.
With its authentic sense of aloha, lush surroundings, and easy access to both the North Shore and South Shore, the Outrigger Kaua‘i Beach Resort is the ultimate gateway to exploring the Garden Isle.
Your Choice of Island Adventure
Choose from three guided adventures during your stay:
- Kaua‘i Movie Sites Tour
Step into the scenes of cinematic legend on this guided journey through Kaua‘i’s most famous filming locations. From the cliffs of “Jurassic Park” to the beaches of “South Pacific” and “Pirates of the Caribbean,” you’ll experience the island’s breathtaking landscapes as Hollywood’s lens once did. Along the way, your expert guide will share behind-the-scenes stories that bring the island’s movie magic to life.
- Waimea Canyon & Fern Grotto Tour
Discover the natural wonders of Kaua‘i on a day of awe-inspiring sights. Begin with the “Grand Canyon of the Pacific”, Waimea Canyon — a kaleidoscope of red, green, and gold cliffs stretching for miles. Then journey to the Fern Grotto, a lush, natural amphitheater draped in hanging ferns and serenaded by gentle island melodies. This tour is a celebration of Kaua‘i’s untamed beauty and tranquil spirit.
- Kōke‘e Adventure
For those who crave exploration, journey deep into the island’s heart on a guided Kōke‘e Adventure. Venture through cool mountain forests, take in sweeping views from Kalalau Lookout, and learn about the island’s rare native flora and fauna. With its combination of rugged trails and panoramic vistas, this experience reveals a side of Kaua‘i few ever see — wild, remote, and soul-stirringly beautiful.
Why This Experience Captivates Donors and Closes Bids
- Freedom to Choose Your Paradise: This isn’t a one-size-fits-all getaway – it’s a tailor-made Hawaiian escape. Donors can choose the island that calls to their spirit – or mix and match multiple islands for the ultimate adventure. From O‘ahu’s vibrant energy to Maui’s golden sunsets, Kona’s volcanic drama to Kaua‘i’s lush serenity, every choice feels like the right one.
- Luxury Meets Authentic Aloha: Each Outrigger Resort embodies the heart of Hawai‘i – where contemporary comfort blends seamlessly with local culture. Whether waking to the sound of waves or dining beneath a sky of stars, every moment feels personal, warm, and unforgettable.
- Adventures for Every Traveler: From snorkeling beside sea turtles and witnessing the sunrise over Haleakalā to exploring volcanoes or attending an oceanfront lūʻau, donors can handpick their perfect experience. This flexibility creates instant emotional resonance – everyone dreams of their own Hawai‘i.
- High Perceived Value & Instant Appeal: With six nights of resort accommodations and curated adventure options, this package offers both luxury and choice – a combination that consistently drives competitive bidding and donor excitement.
- Effortless Planning with Concierge Support: Winspire’s expert concierge handles every detail – from bookings and timing to special requests – ensuring donors enjoy the ease of a fully customized Hawaiian getaway from the moment they say aloha.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major US holidays, Ironman, and other major local events. Additional dates may apply.
Choose Your Paradise and Customize Your Unforgettable Hawaiian Escape
This Experience for 2 Includes:
- 8 nights at a menu of Outrigger Resorts – choose the islands and duration that inspire you most.
- Outrigger Waikiki Beach Resort – City View room
- Outrigger Kona Resort and Spa – Resort view
- Outrigger Kauai Beach Resort & Spa – Garden View room
- Outrigger Ka’anapali Beach Resort – Premium Garden View room
- Your choice of three experiences from a curated selection of adventures
- Winspire booking & concierge service
Experience Hawaii your way with the freedom to choose – or divide your stay between – any of four enchanting islands: O‘ahu, Maui, Kaua‘i, or the Big Island of Hawai‘i. Each eight-night getaway for two includes luxurious accommodations at an Outrigger Resort, and an adventure to explore the island . Dive into history at Pearl Harbor, watch the sunrise over Haleakalā, explore volcanic landscapes in Kona, or cruise through the cinematic beauty of Kaua‘i.
Whether you savor eight serene nights in one paradise or split your stay between multiple islands for the adventure, every moment is curated for wonder, relaxation, and discovery. With Winspire’s expert booking and concierge service, your dream island-hopping Hawaiian escape begins exactly how you imagine it.
Oahu
Outrigger Reef Waikiki Beach Resort: Oceanfront Luxury with the Spirit of Aloha
Set directly on Waikiki Beach, the Outrigger Reef Waikiki Beach Resort is more than a place to stay – it’s a celebration of Hawaiian culture and coastal living. Newly reimagined with elegant island-inspired design, this oceanfront sanctuary offers everything you could dream of in a tropical getaway.
Wake each morning to the sound of waves and views of Diamond Head’s iconic silhouette. Enjoy breakfast by the water at Kani Ka Pila Grille, where live Hawaiian music drifts through the air each evening. Spend your days relaxing by the oceanfront pool and cabanas, indulging in a massage at the La`akea Spa, or stepping straight onto the golden sands for a dip in the Pacific.
The resort’s authentic sense of place sets it apart – from its Hawaiian art collection and welcoming cultural center to the warm hospitality that makes every guest feel like part of the ʻohana (family). With boutique shopping, world-class dining, and legendary Waikiki sunsets just steps away, the Outrigger Reef is the ultimate island retreat.
Your Choice of Island Adventure
Select from two immersive guided tours, each offering a unique perspective of Oahu’s beauty and heritage.
- Oahu Grand Circle Tour
Experience the full grandeur of Oahu on a full-day circle island tour. Travel through lush rainforests, visit sacred sites, and stop at breathtaking viewpoints like Nuʻuanu Pali Lookout. Discover hidden coves, pineapple fields, and the famous North Shore surf beaches, where the island’s natural splendor comes alive.
- Pearl Harbor, Memorial & City Tour
For a deeper look at Hawaii’s story, journey through history at Pearl Harbor. Visit the USS Arizona Memorial, a solemn tribute to courage and sacrifice, before touring Honolulu’s cultural heart – from the royal ʻIolani Palace to the majestic King Kamehameha statue.
Maui
Outrigger Kāʻanapali Beach Resort: Island Luxury with a Spirit of Aloha
Set along one of Maui’s most iconic stretches of shoreline, Kāʻanapali Beach Resort is a paradise where turquoise waters meet golden sands and the warmth of aloha fills the air. Your Premium Garden View Room offers a peaceful haven framed by swaying palms and lush tropical foliage, just steps from the beach and the resort’s vibrant heart.
Each morning begins with the sound of gentle waves and the scent of plumeria drifting through the air. Spend your days basking by lagoon-style pools, snorkeling with sea turtles at nearby Black Rock, or relaxing in a private cabana with a cool drink in hand. For the adventurous, paddleboarding, catamaran sails, and guided ocean excursions await.
Embrace island life with cultural experiences like lei-making, hula lessons, and evening torch-lighting ceremonies. Indulge in a massage using island botanicals at the full-service spa, then savor fresh island cuisine at one of the resort’s acclaimed restaurants. As the sun sets in a blaze of color, the beach transforms into a front-row seat to Maui’s legendary twilight.
With boutique shops, oceanfront dining, and easy access to nearby Lahaina, Kāʻanapali Beach offers the perfect blend of luxury, culture, and relaxation.
Your Choice of Island Adventure
Select from four unforgettable guided experiences – each capturing the essence of Maui’s beauty and spirit:
- Haleakalā Sunrise Tour with Breakfast
Journey to the summit of Maui’s majestic volcano before dawn and watch as the sun rises above the clouds, painting the sky in hues of gold and pink. This once-in-a-lifetime experience is followed by a delicious island-style breakfast to start your day.
- Haleakalā Sunset Tour with Dinner
For those who prefer evening magic, ascend Haleakalā as the sun dips below the horizon, bathing the crater in fiery colors. Afterward, enjoy a leisurely dinner at a local restaurant, reflecting on the day’s beauty beneath a canopy of stars.
- Road to Hāna Adventure
Discover the wild side of Maui on one of the world’s most scenic drives. Wind through rainforests and along ocean cliffs, stopping to explore waterfalls, black-sand beaches, and charming roadside stands filled with local fruit and crafts.
- Best of Maui Food Tour
Savor Maui’s flavors on a guided culinary journey across the island. Visit local farms, sample artisan treats, and indulge in regional dishes that blend Hawaii’s diverse cultural influences – a feast for both palate and soul.
Kona
Outrigger Kona Resort & Spa: Oceanfront Serenity Meets Hawaiian Spirit
Perched dramatically atop lava rock cliffs overlooking Keauhou Bay, the Outrigger Kona Resort & Spa captures the raw beauty and cultural heart of Hawai‘i Island. With breathtaking ocean views, warm island hospitality, and modern amenities, this seaside sanctuary is the perfect place to unwind and reconnect.
Each morning begins with the rhythm of waves against the shore and coffee grown on the volcanic slopes of Kona. Spend your days lounging by the multi-level oceanfront pool, relaxing in the spa, or exploring the nearby tide pools and walking trails. For the adventurous, snorkeling excursions, manta ray night dives, and outrigger canoe rides await just steps from the resort.
As the sun sets, the cliffs glow with golden light and torches flicker to life – a nightly reminder of the island’s natural drama and deep-rooted traditions. With its blend of comfort, culture, and oceanfront wonder, the Outrigger Kona offers an experience that feels authentically Hawaiian.
Your Choice of Island Adventure
Select from two experiences to help bring Kona to life:
- Volcano Adventure Tour
Embark on an unforgettable journey through Hawai‘i Volcanoes National Park, where the island’s fiery heart still beats beneath your feet. Discover steam vents, lava fields, and the immense Kīlauea Caldera as expert guides share stories of Pele, the Hawaiian goddess of fire. Explore the lush landscapes that surround this otherworldly terrain, stop for scenic viewpoints, and enjoy a delicious local-style lunch along the way. It’s a day that captures the raw power and beauty of Hawai‘i in motion.
- Outrigger Kona Lūʻau: Feast & Fire
Experience the magic of a Hawaiian evening under the stars at the Outrigger Kona’s signature Lūʻau. This unforgettable night begins with a traditional lei greeting and continues with cultural demonstrations, live island music, and breathtaking hula performances. As the fire knife dancers ignite the stage, savor a feast of Hawaiian favorites – slow-roasted kalua pork, fresh island fish, tropical fruits, and more. With the Pacific as your backdrop and tiki torches flickering in the breeze, it’s a celebration of aloha you’ll never forget.
Kaua‘i
Outrigger Kaua‘i Beach Resort & Spa: Oceanfront Tranquility on the Garden Isle
Nestled along a golden stretch of shoreline near Līhu‘e, the Outrigger Kaua‘i Beach Resort & Spa is a tropical haven where lush gardens meet the Pacific. Surrounded by swaying palms, cascading waterfalls, and the gentle rhythm of the ocean, this retreat embodies the beauty and serenity that make Kaua‘i unforgettable.
Your stay in a spacious island-inspired room offers private lanai views of vibrant tropical gardens and soothing trade winds. Spend your days floating in one of four sparkling pools – including a sand-bottom lagoon – or strolling the beach as the sun warms the horizon.
Rejuvenate at the oceanfront spa, sip Mai Tais by the pool, and indulge in fresh island cuisine featuring local seafood and produce. Every evening, the sunset paints the sky in hues of gold and rose – the perfect backdrop for a peaceful escape into island time
With its authentic sense of aloha, lush surroundings, and easy access to both the North Shore and South Shore, the Outrigger Kaua‘i Beach Resort is the ultimate gateway to exploring the Garden Isle.
Your Choice of Island Adventure
Choose from three guided adventures during your stay:
- Kaua‘i Movie Sites Tour
Step into the scenes of cinematic legend on this guided journey through Kaua‘i’s most famous filming locations. From the cliffs of “Jurassic Park” to the beaches of “South Pacific” and “Pirates of the Caribbean,” you’ll experience the island’s breathtaking landscapes as Hollywood’s lens once did. Along the way, your expert guide will share behind-the-scenes stories that bring the island’s movie magic to life.
- Waimea Canyon & Fern Grotto Tour
Discover the natural wonders of Kaua‘i on a day of awe-inspiring sights. Begin with the “Grand Canyon of the Pacific”, Waimea Canyon — a kaleidoscope of red, green, and gold cliffs stretching for miles. Then journey to the Fern Grotto, a lush, natural amphitheater draped in hanging ferns and serenaded by gentle island melodies. This tour is a celebration of Kaua‘i’s untamed beauty and tranquil spirit.
- Kōke‘e Adventure
For those who crave exploration, journey deep into the island’s heart on a guided Kōke‘e Adventure. Venture through cool mountain forests, take in sweeping views from Kalalau Lookout, and learn about the island’s rare native flora and fauna. With its combination of rugged trails and panoramic vistas, this experience reveals a side of Kaua‘i few ever see — wild, remote, and soul-stirringly beautiful.
Why This Experience Captivates Donors and Closes Bids
- Freedom to Choose Your Paradise: This isn’t a one-size-fits-all getaway – it’s a tailor-made Hawaiian escape. Donors can choose the island that calls to their spirit – or mix and match multiple islands for the ultimate adventure. From O‘ahu’s vibrant energy to Maui’s golden sunsets, Kona’s volcanic drama to Kaua‘i’s lush serenity, every choice feels like the right one.
- Luxury Meets Authentic Aloha: Each Outrigger Resort embodies the heart of Hawai‘i – where contemporary comfort blends seamlessly with local culture. Whether waking to the sound of waves or dining beneath a sky of stars, every moment feels personal, warm, and unforgettable.
- Adventures for Every Traveler: From snorkeling beside sea turtles and witnessing the sunrise over Haleakalā to exploring volcanoes or attending an oceanfront lūʻau, donors can handpick their perfect experience. This flexibility creates instant emotional resonance – everyone dreams of their own Hawai‘i.
- High Perceived Value & Instant Appeal: With eight nights of resort accommodations and curated adventure options, this package offers both luxury and choice – a combination that consistently drives competitive bidding and donor excitement.
- Effortless Planning with Concierge Support: Winspire’s expert concierge handles every detail – from bookings and timing to special requests – ensuring donors enjoy the ease of a fully customized Hawaiian getaway from the moment they say aloha.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major US holidays, Ironman, and other major local events. Additional dates may apply.
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