Private Jet Island Hopping to Tokyo’s Wild Side: A 4-Night Journey to Tokyo Islands

Sponsored Content: This article was produced in collaboration with Tokyo Takarajima.

Tokyo has been ranked the No. 1 city in the world in the Best Big Cities category for the second consecutive year in the 2025 Readers’ Choice Awards by Condé Nast Traveler. Celebrated globally as a megacity of neon lights, cutting-edge culture, and endless energy, Tokyo continues to captivate travelers. Yet beyond its skyline lies a very different Tokyo—one that few ever encounter.

Stretching south into the Pacific Ocean is a chain of eleven volcanic islands, where mountains rise from the sea and forests grow from volcanic soil. This is Tokyo’s wild side, shaped by ancient eruptions and surrounded by remarkably clear waters.

This article introduces private jet travel from overseas to Hachijojima and Oshima, together with a recommended 4-night island-hopping itinerary offering access to volcanic landscapes, island culture, and a side of Japan rarely experienced by international travelers.

Reaching Tokyo’s Islands Directly from Abroad by private jet

By private jet, travelers can cross continents and arrive directly to the Tokyo island region, bypassing long transfers and ferries. Private jets can land on Hachijojima and Oshima, making these remote islands surprisingly accessible. For travel between islands, travelers may continue by private jet where available, or choose to charter helicopters, which offer sweeping aerial views of calderas, dramatic cliffs, and deep-blue waters—turning transportation itself into part of the experience.

A 4-Night Journey Across Two of the Tokyo Islands

This 4-night island-hopping itinerary introduces two distinct islands—Hachijojima and Oshima—each offering a different expression of volcanic nature and island culture.

Hachijojima: A Year-Round Spring Island Shaped by Nature and Island Life

Located 286 kilometers south of central Tokyo, Hachijojima Island is home to just about 6,700 residents and is known for its subtropical climate, dramatic lava flows, and deep-blue “Hachijo Blue” waters. These clear seas are home to green sea turtles that inhabit the surrounding reefs. The island’s culture is deeply tied to its environment—from traditional Kihachijo silk, dyed with local plants, to island cuisine shaped by the surrounding sea. Over long stretches of time, the island’s landscape has given rise to clear streams, as well as waterfalls and natural hot springs—an abundance of gifts from nature. Hachijojima may be small, but its cultural and culinary traditions are remarkably rich, carefully carried forward by generations of islanders to this day.

Oshima: Walking the Earth’s Pulse

Closest to Tokyo yet strikingly untamed, Oshima Island (Izu Oshima) is defined by Mt. Mihara, an active volcano that rises at the heart of the island. Walking across hardened lava fields and vast black volcanic deserts, visitors can feel the raw power that has shaped the island, while offshore, exceptional water clarity and frequent sightings of hammerhead sharks draw divers from around the world. Over the long winter months, nearly three million camellia flowers gradually come into bloom, followed in spring by Oshima cherry blossoms that tint the mountains in soft pink. As warmer seasons arrive, vibrant greens spread across the island, creating a striking fusion of stark volcanic landscapes and richly colored natural beauty.

What is there to experience on the islands?

On these islands, the experience is defined not by extravagance, but by contrast. In just a few days, travelers move from one of the world’s largest cities to places where stars fill the night sky, meals are prepared with ingredients harvested the same day, and local communities welcome visitors not as spectators, but as guests.

Along the way, you can experience:

• Clear Pacific waters, home to vibrant marine life, including sea turtles and diverse fish species
• Living island cultures, from traditional textiles and drumming to crafts shaped by local materials
• Island cuisine rooted in place, made with seafood and produce harvested the same day
• Volcanic landscapes and ancient terrain, shaped by eruptions and time
• Genuine human connection, where visitors are welcomed into communities rather than staged experiences
• Night skies untouched by city lights, where stars dominate the horizon

Itinerary｜4 Nights Island-Hopping Through Tokyo’s Islands

Day 1: Arrival to Tokyo’s Island Region

Arrive in Japan by private jet and fly directly to Hachijojima, one of Tokyo’s remote volcanic islands. For this itinerary, a private jet carrying a group of high-end travel agents from Los Angeles made the journey, highlighting how seamlessly these islands can be reached from overseas.

After arriving on the island and taking a moment to settle in, enjoy a hands-on Kihachijo weaving experience at Hachijo Folk Crafts Yamashita. Learn the process behind Hachijojima’s traditional silk, woven from threads dyed with local plants, and create your own 4.7 × 4.7-inch mat to take home as a meaningful souvenir.

In the evening, enjoy a relaxed dinner at Ryozanpaku, a dining venue rooted in the island’s culinary traditions, where locally sourced seafood and seasonal island vegetables take center stage. The day concludes with a quiet night under star-filled skies.

Day 2: Exploring Hachijojima

After resting at the island hotel, surrounded by quiet ocean air, spend the day discovering Hachijojima’s landscapes and everyday life.

In the morning, head to Fureai Farm on the slopes of Hachijo-Fuji, where sweeping views open across the town and the Pacific, with Mt. Mihara visible on the far side of the island. Enjoy an ice cream made with local Jersey milk as you take in the panorama.

For lunch, visit Isozakien, a stone-walled traditional home serving island dishes rooted in local culinary heritage and prepared with fresh, locally sourced ingredients. Afterward, continue to Uramiga-taki Waterfall, where you can step behind the cascading water and enjoy the cool, forested surroundings.

Later, unwind at Kirameki Foot Bath, an open-air onsen where you can soak your feet while gazing out toward the horizon—during winter, migrating whales are sometimes visible offshore. As evening approaches, head to the Nanbara Coast of Permian Rocks to walk across a vast lava plateau and watch the sunset over the ocean.

After a full day on the island, enjoy dinner at Aigae Suisan, a cozy eatery run by a local fish producer, specializing in Hachijojima’s famed kusaya alongside fresh local seafood—an authentic close of the day.

Day 3: Island Hopping to Oshima

Travel by a chartered helicopter to Oshima, taking in a vast aerial panorama of the Izu Islands, with volcanic ridges and dramatic coastlines stretching out below.

For lunch, stop at Nadai Utanochaya to enjoy set meals featuring camellia oil tempura and ashitaba-flavored udon, dishes rooted in the island’s culinary traditions.

In the afternoon, explore Mt. Mihara, Oshima’s active volcano. Walk across hardened lava flows and stark black volcanic landscapes, where the power of nature is impossible to miss.

Along the coastal road, catch glimpses of the Great Road Cut, a dramatic 2,070-foot stretch of exposed volcanic layers.

Later, experience Camellia Petal Dyeing at Atelier Koharu, where silk is dyed using petals of Camellia japonica. The soft pink tones gradually fade into gentle beige, creating a fabric that continues to evolve over time.

From there, continue with a boat trip along the rugged coastline, passing towering cliffs and offshore formations shaped by volcanic activity over thousands of years. In the evening, dine at Kissa Sakaba Nabekichi, a relaxed café-bar serving island classics and local–Hawaiian fusion dishes, including its popular Hawaiian-style Bekkou rice bowl.

Day 4: Culture, Nature, History and a Return to Hachijojima

After a relaxed breakfast at the hotel, head to Habu Port, once a thriving wind-waiting port. Stroll through its preserved streets and visit the local museum to glimpse the island’s maritime past, where history still quietly lingers.

Next, explore Urasabaku—The Black Desert, a vast stretch of black volcanic sand spreading across the slopes of Mt. Mihara. Its open, otherworldly landscape offers striking photo opportunities. Continue to Senzu Path Cut, where massive tree roots wrap around a stone wall, revealing a hidden staircase that blends nature and history.

For lunch, stop at Kaisenchaya Sushikou to enjoy fresh local seafood—from sashimi to rice bowls—served with sweeping ocean views. In the afternoon, visit Takada Oil Factory to see camellia oil crafted from locally harvested Camellia japonica seeds using the traditional tamadome shibori method, followed by a stop at the Volcano Museum, newly renovated and reopened in July 2025, where immersive exhibits and a VR theater bring Oshima’s volcanic story to life.

In the late afternoon, return to Hachijojima and unwind at a sunset yoga retreat overlooking lava fields and a nearby uninhabited island. The journey concludes with a barbecue under the stars, shared with local residents and accompanied by Hachijo Taiko drumming and the Kashitate hand dance—a warm farewell rooted in community and connection.

Last Day: Experience Island-Style Sushi Before Departure

On the final day of your Tokyo island adventure, try making the island’s specialty sushi. Fresh fish marinated in a soy-based sauce is served with mustard instead of wasabi, guided by Hachijojima’s renowned proprietress, Eiko-ba. After enjoying the sushi you made yourself, along with other island dishes prepared by Eiko-ba, your journey comes to an end.

Board a private jet back to Los Angeles, savoring a relaxed flight while reminiscing about the nature, food, and people you encountered on the islands.

Skipping Oshima? Must-Try Experiences for Those Not Visiting Oshima

Even if you decide not to go island-hopping to Oshima, Hachijojima offers plenty of unique experiences for travelers seeking adventure, culture, and local flavor.

Underwater Scooter with Arabesque

Explore “Hachijo Blue” on an underwater scooter and spot sea turtles in their natural habitat. The tour is operated by the Diving shop Arabeque.

Hachijo-Kojima Boat Trip with Project Wave

Visit the uninhabited Hachijo-Kojima, abandoned since 1969, and discover its wild, lush landscapes. Project Wave operates the tour.

Aogashima Helicopter Tour by Toho Air Service

Enjoy breathtaking aerial views of the tiny volcanic island and its dramatic cliffs. Toho Air Service operates this tour.

Kusaya Factory at Osada Shoten

See how this famous fermented fish is made and learn about the traditional process at Osada Shoten.

Hachijojima Spirits Tasting at Hachijou Kouhatsu

Tour a local distillery and taste shochu crafted with pristine island water at Hachijou Kouhatsu.

Ubaihomei Shrine

Step into a 1,000-year-old shrine called Ubaihomei, surrounded by sago palms dating back 700 years.

Kuriya Restaurant (Currently Closed)

Try Hachijojima’s signature “Ashitaba Tsukemen”—udon infused with ashitaba and crispy tempura.

SEA SIDE KITCHEN WA (Currently Closed)

Island-inspired burgers with Hachijo lemon and flying fish lemon, served by the sea.

Ready to Discover Tokyo Beyond the City?

This 4-night private jet island-hopping journey offers a rare opportunity to experience Tokyo from an entirely new perspective. Remote yet accessible, raw yet welcoming—the Tokyo Islands invite you to discover a Japan that remains beautifully unspoiled.

*This article and the video were reported in September 2025.