Luxury holidays in Hawaii

Why should you travel on a luxury Hawaii vacation with us?

Cast adrift in the Pacific Ocean, the wildly beautiful emerald-hued islands of Hawaii are like nowhere else on earth. There are few places in the world where you’ll find such a heady mix of blissful beaches, millenia-old volcanoes, and thundering waterfalls, where you can relax one day and feel an adrenaline surge through your body the next.

So why take a luxury Hawaii vacation with us? It’s all in the details. Take surfing. We won’t just arrange a surf lesson, but instead we’ll create a class for the curious that’s taught by a legendary grand master. It’ll blend the history of the sport and its important place in Hawaiian culture, with thrilling, hands-on learning. We’ll guide you up mountains (and back down again, at speed), take you turtle-spotting on the ocean, and lower you into volcano craters in a helicopter. In fact, every single one of our Hawaii island tours is the definition of extraordinary.

In Hawaii, there truly is something for everyone. And our entirely bespoke trips to Hawaii will help you connect with the land and the energy of this incredibly special state.

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What to see and do in Hawaii

Pedal at sunrise down Maui’s tallest peak

It’s worth every bleary-eyed minute of your early morning wake up call to see the sun breaking over the cloud at Haleakalā – the national park’s namesake volcano that doubles as Maui’s highest peak, at a staggering 6,500 feet. That’s the slow start to the day before the thrilling bike ride back down the mountain – soaking up Pacific Ocean views along the way. They say coffee perks you up in the morning. This descent? Even better.

Swoop over “Jurassic Park Falls” in a helicopter

To really appreciate Hawaii’s natural beauty, you need to take a bird’s eye view over the Garden Isle of Kauai. On this Hawaii island tour, your helicopter will glide through the sky to the likes of Mana Waiapuna, made famous by the Hollywood blockbuster, Jurassic Park. Next, it’s on to the canyons, including Waimea Canyon, the “Grand Canyon of the Pacific” with its hundreds of hidden waterfalls. And, if the weather says so, we’ll lower into the heart of the crater of Mt Waialeale volcano, surrounded by 5,000-ft walls and 3,000-ft-high waterfalls – a once-in-a-lifetime experience that you won’t forget in a hurry.

Island hop around Maui and Kauai

How do you like your beaches? Your favorite – until now – may be a small, peaceful bay fringed by palms and lapped by gentle waves. Or perhaps you like them a little crazier – huge human-height waves falling onto treacle-colour sand? We’ll take you on a tailor-made tour of the sun-kissed islands of Maui and Kauai, seeing the dramatic volcanic landscape from the water, and pitching up at some of our favorite stretches of sand. These are the ones we love – and the ones we know you’ll love, too.

Catch waves with a Grand Master

Surfing in Hawaii is less of a sport and more of a way of life. For centuries, the practice was called ‘he’e nalu’ or ‘wave sliding’ – an artistry that respected the profound power of the ocean. To really understand Hawaii today? You need to tackle the waves – and who better to help you than a grand master acting as your tutor and guide? Part history lesson, part heart-racing workout, this is surfing as you’ve never experienced it before.

Snorkel with candy-colored marine life in Maui

Hawaii doesn’t limit its wonders to eye level. What dazzles the most here is beneath the surface, meaning that a snorkeling trip is no ordinary swimming experience. We’ll charter a private boat – which means your adventure is entirely bespoke – and drop anchor at the snorkeling spots that work for you. Beginners may love the calm, quiet waters sheltered by a natural reef at Baby Beach. Others may like to swim alongside sea turtles and harmless reef sharks at Mala Wharf. And for rainbow-hued coral gardens? How about leaping off the deck into the highlighter-blue water at Olowalu Beach Park?

The best of Hawaii

FAQs

Everything you need to know about visiting Hawaii with Black Tomato

What is the best island to visit in Hawaii for a luxury vacation?

Each Hawaiian island offers a genuinely different experience, and the right one depends entirely on what you want from a trip. Maui is our most-requested island — it has the widest range of luxury hotels, Haleakala’s sunrise, excellent snorkeling, and easy access to whale watching in season. Kauai is more remote and dramatic, with fewer crowds, the Napali Coast, and the best helicopter experiences in the archipelago. Oahu combines city energy in Honolulu with historical depth at Pearl Harbor and the surf culture of the North Shore. Big Island is the choice for those who want to get closest to Hawaii’s volcanic geology, with lava flows, stargazing from Mauna Kea, and working coffee farms. We typically recommend at least two islands on a first luxury Hawaii vacation.

How long should a luxury Hawaii vacation be?

For a single-island luxury Hawaii vacation, seven to nine nights is sufficient to explore properly without feeling rushed. Combining two islands — Maui and Kauai is our most popular pairing — works well over ten to twelve nights. Extending into French Polynesia or California adds five to seven days and creates a compelling Pacific journey. We design every itinerary around your available dates and what you most want to experience.

How much does a luxury Hawaii vacation cost?

Luxury Hawaii vacations typically start from around $7,000 per person for an eight-night itinerary on a single island, rising for multi-island trips, private villa accommodation, and chartered boat or helicopter experiences. A comprehensive twelve-night trip combining Maui and Kauai with private activities and top-tier hotels will usually fall between $10,000 and $15,000 per person. We price every vacation individually based on your dates, group size, accommodation preferences, and the experiences you want — and there are no planning fees.

What are the best experiences on a luxury Hawaii vacation?

The experiences that consistently define luxury Hawaii vacations are surfing with a grand master on Kauai, the Haleakala sunrise followed by a 23-mile bike descent on Maui, a private helicopter flight over Kauai into the crater of Mt Waialeale, snorkeling aboard a private chartered boat, and island-hopping between Maui and Kauai. For those wanting cultural depth, joining the Treecovery Hawaii replanting effort in Lahaina — where the 2023 wildfires destroyed much of the town — is among the most meaningful experiences we offer anywhere. We build every itinerary around which of these suit your group.

Is Hawaii good for a luxury family vacation?

Hawaii is exceptional for families. The combination of accessible outdoor adventure, warm water, and cultural depth works for every age. Children are captivated by snorkeling with sea turtles, learning to surf, and the sheer drama of Haleakala at sunrise. Teenagers engage immediately with the surf culture, the helicopter rides, and the volcanic geology. The Treecovery Lahaina experience, planting a sapling as part of the recovery effort, is particularly powerful for families wanting to give something back. We design every Hawaii family vacation around your group’s ages, interests, and pacing preferences.

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