Maui: the ultimate week of exclusive adventures for high-net-worth travelers
Beyond the well-traveled paths of Maui lies a world of extraordinary experiences waiting to be discovered. Allow us to guide you through seven days of elevated island living, where each moment is crafted to surpass the expected and deliver the exceptional.
Day 1: Arrival & oceanfront indulgence
Morning & afternoon
Your Maui journey begins with a private car transfer from Kahului Airport to the Four Seasons Resort Maui at Wailea.
As you arrive at this oceanfront sanctuary, experience the time-honored tradition of a personalized lei greeting, setting the tone for the days ahead. Take time to settle into your suite, perhaps enjoying a quiet moment on your private lanai as you acclimate to island time.
Evening
As the day cools, make your way to Ferraro's Bar e Ristorante, where refined Italian cuisine meets Pacific ambiance. Dine in the open air under the stars, accompanied by the gentle rhythm of waves meeting the Wailea shore.
Day 2: Ocean sanctuaries
Morning
Dawn brings your first encounter with Maui's marine treasures aboard Satisfaction, our 57' Sunseeker Predator. While others join crowded tours to Molokini Crater, you'll experience this marine sanctuary in refined privacy. Our onboard crew guides your exploration of this crescent-shaped wonder, sharing insights about the remarkable ecosystem that thrives within these protected waters.
Afternoon
Return to your resort to unwind by the pool or beach, perhaps reflecting on your morning's discoveries while enjoying the attentive service that makes the Four Seasons legendary.
Evening
As golden hour approaches, rejoin Satisfaction for our signature sunset cruise. Sip expertly crafted cocktails while watching the sun paint the sky in hues of gold and purple – during whale season (December through April), you might even witness the majestic breach of a humpback whale.
Day 3: Cultural and culinary delights
Morning
Begin your journey along the legendary Road to Hana, where each turn reveals another of Maui's secrets. Your guided tour brings you to hidden waterfalls and secluded beaches, offering insights into the rich history that makes this journey so much more than a scenic drive.
Afternoon
Continue your Road to Hana adventure, perhaps stopping at local fruit stands or taking in the view at one of the many scenic overlooks that dot this famous highway.
Evening
As twilight approaches, experience the Feast at Mokapu at the Andaz Maui, where the traditional luau is elevated to an art form. Savor premium cuisine while master practitioners share the stories of ancient Hawaii through music and dance.
Day 4: Summit awakening
Morning
Rise early for your guided helicopter journey to witness sunrise atop Haleakalā. Standing at 10,023 feet, watch as first light reveals the magnificent crater and distant islands – a perspective that has inspired wonder for generations.
Afternoon
Descend into Maui's Upcountry, where elevated agriculture meets island sophistication. Enjoy lunch at a local eatery in the Kula area, known for its farm-to-table cuisine, followed by visits to local lavender farms or Maui’s local winery for tastings.
Evening
Return to sea level for a relaxed evening, perhaps enjoying dinner at your resort or discovering one of Wailea's many fine dining restaurants.
Day 5: Marine encounters & coastal flavors
Morning
During whale season (December-April), return to Satisfaction for an intimate whale watching experience. Our vessel's design offers unparalleled viewing opportunities while maintaining the privacy our guests value.
Afternoon
Spend time at Wailea Beach, where pristine sands and crystal waters provide the perfect setting for afternoon relaxation.
Evening
Complete your day at the legendary Mama's Fish House, where today's catch becomes tonight's masterpiece. Arrive early to enjoy one of their signature cocktails as the sun sets over the North Shore.
Day 6: Adventure & serenity
Morning
Begin with an exhilarating zipline adventure over Maui's verdant landscapes, offering a bird's-eye view of the island's dramatic topography.
Afternoon
Return to your resort for wellness time, experiencing the transformative touch of a traditional Lomi Lomi massage at the spa.
Evening
Find yourself at the adults-only Serenity Pool, where sunset becomes a celebration. Watch as day fades into night while enjoying premium cocktail service in this sophisticated setting.
Day 7: Graceful farewell
Morning
Savor your final island morning with an unhurried breakfast overlooking Wailea Beach, perhaps enjoying fresh local fruits and Kona coffee.
Afternoon
Take time to collect a few carefully chosen mementos, exploring the resort's boutiques or nearby luxury shops for that perfect reminder of your Maui journey.
Evening
As your time on island draws to a close, your private transfer ensures a seamless departure from your oceanfront sanctuary to Kahului Airport.
Planning your journey
For ocean adventures aboard Satisfaction:
Morning Molokini excursions include premium snorkeling equipment and marine naturalist guidance
Whale watching experiences available December through April
All charters limited to 6 guests for ultimate privacy
Expert crew trained in luxury hospitality
Custom itineraries available upon request
Ready to begin your Maui experience? Contact our concierge team at (808) 866-0338 to seamlessly integrate Satisfaction's private charters into your luxury island journey.