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Experience thrills and chill on four of Hawai’i’s major islands
Imagine experiencing four of Hawaii’s most spectacular islands with exclusive access and travel by private plane. That’s exactly what you’ll do on TCS World Travel’s trip, Uncharted Hawaii by Private Jet. Along the way, you’ll witness less-visited parts of Kauai, Maui, Lanai, and the Big Island of Hawaii, balancing adventure with relaxation for the ultimate vacation.    

You’ll fly via chartered jet, a mode of travel that allows you to avoid large airports and layovers, choose your companions, and decide exactly what you want to do. For flexibility, convenience, and safety, there’s never been a more advantageous time to travel by private plane.  

This itinerary is designed for you to travel with the companions of your choosing (with a recommended group size of 4–12 people). The trip can be customized to your interests, specifications, and group, and departs whenever works for you (though the best months to travel are October through May).  

Moving at a moderate pace, you’ll explore the best of each island. Kauai offers the perfect mix of towering mountains and sunny beaches, while Maui features turquoise water, farm-to-table cuisine, and breathtaking sunsets. Lanai boasts secluded sands and tropical trails, and the Big Island of Hawaii brings varied landscapes, from fiery volcanoes to snow-capped peaks. In each destination, you’ll have the chance to create a one-of-a-kind itinerary just for you. 

However you decide to customize your trip, TCS will make sure you travel in style. Everything from travel by private jet, car, and helicopter to hotel stays, daily activities, and top-notch guides is included in your journey.
  • Cost
    $50,500 per person double occupancy, based on six guests traveling together. Prices vary based on group size, departure airport, and other customizations.
    Package Pricing Includes:
  • Itinerary
    13 Days
  • Days 1–3 Kauai
    Days 4–6 Maui
    Days 7–9 Lanai
    Days 10–13 Big Island of Hawaii
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    Days 1–3
    You’ll start your journey on beautiful Kauai, famous for its dazzling scenery and easygoing atmosphere. Dotted with lush valleys, jagged peaks, and plunging cliffs, the island is also home to tropical rainforests, rivers, and waterfalls, as well as plenty of tranquil beaches.  

    While here, you’ll have the chance to explore both the north and south shores, which feature dramatically different landscapes due to past volcanic eruptions and low-pressure weather systems in the North Pacific. The north is known for its dramatic cliffs, while the south is renowned for its picturesque beaches. Plan a day trip to Ni’ihau—known as “the forbidden island” because it only recently began allowing visitors—to snorkel, swim, and discover a traditional way of island life, or stay on Lanai for a day of surf lessons at Poipu Beach and local brews at a Kauai-style happy hour. You’ll also want to save time to experience the island’s incredible shopping and dining scenes.  

    Your home base on Kauai will be the sophisticated Lodge at KuKui’ula, which boasts stylish cottages and bungalows along with sweeping ocean views. As a guest, you’ll have access to luxurious amenities like a sprawling golf course, spa, and lagoon-style pools.
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    Days 4–6
    En route via private jet to Maui, you’ll make an unforgettable stop on remote Molokai, called the “Friendly Isle” for its rich Hawaiian culture. Steeped in tradition, the island offers a chance to step back in time by visiting the birthplace of hula, touring a royal coconut grove, or discovering a variety of historic sites.  

    Afterward, you’ll fly to Maui, where you can look forward to migrating whales, farm-to-table cuisine, and sunset views from the top of Haleakala volcano. You’ll base your stay at the chic Montage Kapalua Bay, with its residential-style accommodations, lush gardens, award-winning spa, and Pacific Ocean views.    

    During your time on Maui, you can try everything from ziplining through the forest to exploring local farms. Summit Haleakala just in time to catch the sunrise, then bike down the volcano, navigating switchbacks and enjoying the expansive views below. If you’d rather witness Haleakala from above, take a helicopter ride over the volcano and the coast, then touch down in Hana on Maui’s rugged eastern shore to hike in bamboo forests and soak in sacred pools.
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    Days 7–9
    After some time on Hawaii’s second-largest island, you’ll be ready for the 20-minute private flight to the archipelago’s most secluded destination: Lanai. Once completely covered by a pineapple plantation, the small, serene island offers the ideal mix of adventure and relaxation.  

    The smallest inhabited island of Hawaii, Lanai has far fewer crowds than other Hawaiian hotspots. Take advantage of that fact by going completely off the grid—disconnect on a beautiful beach, or get lost exploring jungle trails by foot or horseback. You could also opt for a sunrise hike to Pu’upehe, a triangular sea stack with a fascinating history; a day of deep-sea fishing for mahi-mahi, yellowfin tuna, and marlin aboard a high-speed private vessel; or an ATV tour of Lanai’s rugged terrain, with visits to the famous Garden of the Gods, picturesque beaches, and tall bluffs overlooking the ocean.  

    While on Lanai, you’ll stay at the plush Four Seasons Resort on the island’s southeastern coast. With lagoon-style pools, botanical gardens, a tranquil spa, and gourmet restaurants, the hotel makes a strong case for never leaving the property.
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    Days 10–13
    Big Island of Hawaii
    Your journey will conclude on the Big Island—the largest land mass of all the Hawaiian Islands. Here, you can experience multiple climate zones as well as diverse scenery and landscapes.  

    On the Big Island, lush valleys and shady beaches meet active volcanoes and snowy mountains. Ascend Mauna Kea—at 14,000 feet, it’s the tallest volcano in the world—to see a striking sunset and stargaze the night away, or take an aerial tour of Hawaii Volcanoes National Park, soaring over frozen lava flows, massive craters, cascading waterfalls, sheer cliff faces, and remote coastlines. For something slightly less hair-raising, tour a coffee farm and discover the secrets of Kona beans, or keep the adventure going with a nighttime snorkel in the illuminated waters of Manta Village, where you can swim alongside giant manta rays.  

    You’ll end your Hawaiian getaway in comfort at the Mauna Lani, Auberge Resorts Collection, set amid the peaceful beaches, coral reefs, and ancient fishponds of the dramatic Kohala Coast. Understated yet elegant, the property boasts private cabanas, ocean views, and three separate pools, each with its own personality.