A Luxury Hawaii Adventure by Land, Sea & Sky with WSJ+

We’re working with WSJ+ to create entirely customizable and private trips for you, their members. Our Travel Experts are here to make your trip entirely your own. Private, customizable, and totally flexible. This is what we do. This month, we’re introducing a new highlight itinerary to Hawaii that you can embark on today. Take it ‘as is’ or customize it to your heart’s content.


An opportunity to rest and reflect as well as immerse yourself and explore, this is eight big nights in Hawaii experiencing the best these incomparable islands have to offer. Helicopter into volcanic craters on Kauai before snorkeling beneath the moonlight with manta rays off Big Island. For each high-octane moment, there’s one of tranquility; with dolphins encountered in the morning light of the Na Pali coast and hidden waterfalls inviting an afternoon swim. A sunset sail up the Kona coast by private catamaran completes the experience.

To add extra magic to your time away, WSJ+ members will enjoy a complimentary sunrise Hawaiian outrigger canoe experience. See the sunrise over Mauna Kea as you embrace ancient Hawaiian tradition and discover the significance of wa’a (canoeing) in local life.

Exclusive to WSJ+ members

This trip has been designed exclusively for WSJ+ members, drawing on our travel experts’ in-depth knowledge of Hawaii. The experience, however, is yours and yours alone, with all of our trips private and customisable. What you’ll find below, therefore, is simply a suggestion. Our Travel Experts will work with you to devise an itinerary based on your inquiry, budget, group size, and desires. Typically, this will include everything from the experiences you do (and the guides that will take you there) to the hotels you’ll bed down in and the trains, planes and automobiles that will take you in between. We can also help with international flights, if you like.

WSJ+ members will receive:

  • Immersive experiences tailored to your interests. This could include anything from doors-off helicopter flights to after-dark snorkel trips in the company of manta rays.
  • Exclusive benefits to elevate your experience.
  • Stays at Hawaii’s most luxurious hotels and resorts.
  • Access to expert guides throughout.
  • Up-to-date COVID travel advice – including arrangements for any required PCR testing whilst traveling.
  • Unrivalled expertise in planning your trip to Hawaii.

Make this itinerary yours

Like what you see? Contact us today to find out more about our exclusive itineraries. But remember: each and every Black Tomato trip is tailored exactly to who you are and what you want to do so tell us about yourself and we’ll create something that’s entirely you.

Start Planning Here

What to do

Start your trip on the incomparably beautiful island of Kauai where we’ll arrange for you to take off on a helicopter tour. A flight straight out of fantasy, the experience will see you flying beneath the arc of crisp, clear rainbows in Hanapepe Valley, past the mighty 400ft high Manawaiopuna Falls made famous by Jurassic Park, and through the ‘Grand Canyon of the Pacific’, Waimea Canyon. This all culminates, quite spectacularly, at Mt Waialeale volcano where you’ll fly into the crater to see waterfalls cascade thousands of feet to the valley below.

Mixing relaxation with adventure, the next few days will see you explore Kauai from all angles. On land, we’ll arrange a tropical horseback trail ride that will lead you to across an ancient volcanic caldera for a swim in a hidden waterfall. Whilst out at sea, a morning zodiac expedition along the Na Pali Coast will see you dart in and out of sea caves and plunge beneath cascading waterfalls in the company of a resident pod of Hawaiian Spinner dolphins.

Over on Big Island, the adventure continues as you get to know the island from dawn ’till dusk. Start off beneath the moonlight on an after-dark snorkelling tour that will see you gliding alongside manta rays before waking up the next morning for a WSJ+ member-exclusive experience, paddling out to sea by traditional outrigger canoe to watch the sunrise over Mauna Kea. Your days are yours to enjoy at leisure, but might we also suggest a guided tour of Hawaii Volcanoes National Park? The crown jewel of Big Island, spend some time hiking amid dormant and active volcanoes, miles of lava beds and the famed Sulphur Banks, learning about how recent eruptions have changed the face of the park. For a fitting final send-off, we’ll then arrange for you to enjoy a private sunset sail along the Kona coast, watching the sky set itself ablaze as the sun drops down behind this volcanic island.

Where to stay

Throughout your trip, you’ll stay in the best hotels and resorts Hawaii has to offer. On Kauai, that means the Grand Hyatt Kauai Resort & Spa. Seldom surpassed, feel yourself slip into a steady state of relaxation by one of the property’s four pools and listen in to the call of the resident macaws. Later on, retreat to the tranquil embrace of the spa, set amid jungle waterfalls before indulging at Tidepools restaurant, located atop a series of koi ponds.

On Big Island, we’ll put you up at the newly-opened Mauna Lani by Auberge Resorts Collection. A luxurious beachfront property full of Hawaiian culture and storytelling, it’s the ideal spot for soaking up island life. Spend some time chatting with Uncle Danny, the resort’s own Kahu Hanai, a guardian of the island’s secrets, before embracing the integral connection between land and sea, Mauka and Makai, over dinner at the CanoeHouse.