Iconic
Princeville
1 Hotel Hanalei Bay
Sustainable-luxury wellness flagship on the former St. Regis site, with six restaurants, two pools, and private Honoiki Beach below the Bali Hai peaks.
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For private groups
An island built for the buy-out.
Every signature Kauai experience has an exclusive-use version. We assemble them into one seamless week.
Design This TripKauai is built for buy-outs. Charter a full Na Pali catamaran with Holo Holo or Captain Andy's, book a private helicopter with Mauna Loa, and a private sportfishing boat out of Nawiliwili. Every signature experience has an exclusive-use version.
One radius, no long transfers
Lodging anchors well around Poipu and Koloa, the Grand Hyatt or luxury villa rentals at Kukui'ula on the sunny south, or Princeville and Hanalei for North Shore drama and privacy. A private farm dinner at Common Ground gives the group a shared evening centerpiece, and the island's small scale means air, sea, and land all sit within a tight radius.
We coordinate the manifest across boats, flights, and tables, stage the group dinners, and keep a single point of contact for the whole party.
What’s inside
- Full-boat Na Pali charters, exclusive use
- Private helicopter and private sportfishing
- Villa estates or a resort base on the south shore
- A private farm dinner as the group centerpiece
- Air, sea, and land within a tight radius
A sample rhythm
- 01
Gather
A villa estate or resort base, a relaxed first group dinner.
- 02
Sea day
A full-boat Na Pali charter for the whole party.
- 03
Split & choose
Private flights, fishing, golf, and spa in parallel.
- 04
Centerpiece
A private farm or oceanfront dinner to close the week.
The Kauaiwe’d build in
The pieces that fit this trip.
Where to stay
Resorts and residences that hold the coastline.
From a North Shore wellness flagship to villa estates on the sunny south, these are the stays a Kauai trip is built around.
Iconic
Poipu
Grand Hyatt Kauai Resort & Spa
The island's defining resort on Shipwreck Beach: a saltwater lagoon, lazy river, the vast Anara Spa, and Poipu Bay golf at the door.
Visit official siteMICHELIN Key
Lihue
Timbers Kauai Ocean Club & Residences
Oceanfront two-to-four-bedroom residences on the 450-acre Hokuala resort, MICHELIN Key two years running, with 17 miles of trail and the Ocean Course.
Visit official siteAdults-leaning
Poipu
Ko'a Kea Resort on Poipu Beach
An intimate 121-room oceanfront boutique built for romance and seclusion, home to the acclaimed Red Salt.
Visit official siteBest for families
Poipu
Koloa Landing Resort, Autograph Collection
Villa-style resort with full Wolf and Sub-Zero kitchens and a 350,000-gallon pool complex, a short walk from reef-protected Poipu Beach.
Visit official siteTop rated
Princeville
The Cliffs at Princeville
Spacious clifftop suites a hundred feet above the Pacific on a 22-acre North Shore plateau, ideal for longer, independent stays.
Visit official siteNa Pali by sea
The coast you cannot reach by road.
The Na Pali cliffs only reveal themselves from the water. Private full-boat charters are the luxury way to see them.
Na Pali boat season runs roughly May to September; winter swell can cancel North Shore departures.
Top rated
Port Allen
Holo Holo Charters
Repeatedly voted Hawaii's top boat tour, running the bucket-list Na Pali and Ni'ihau crossing on a purpose-built 65-foot catamaran.
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Port Allen
Captain Andy's Sailing Adventures
Kauai's original Na Pali operator since 1983, with luxe Star Class sailing catamarans for sunset and snorkel sails.
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Port Allen
Blue Dolphin Charters
Forty years on the coast, 65-foot catamarans with snorkel, sunset-dinner sails, and seasonal whale watching.
Visit official siteIntimate
Hanalei
Na Pali Catamaran
The only tour catamaran departing Hanalei Bay, nimble enough to slip into the lava-tube sea caves.
Visit official siteBluewater
Marlin, mahi, and ono off Nawiliwili.
Private sportfishing charters run year-round from Nawiliwili Harbor for Pacific blue marlin, mahi-mahi, ono, and ahi.
Top rated
Nawiliwili
Captain Don's Sportfishing
A thirty-year local captain aboard a 39-foot Hatteras, private four, six, and eight-hour charters.
Visit official sitePrivate group
Nawiliwili
Go Fish Kauai
Private charters aboard a 41-foot Bertram Sport Fisher with a six-seat flybridge, comfortable for a group.
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Nawiliwili
Imua Fishing Charters
Locally owned, a captain with Pacific commercial-fishing background, well regarded for private trips.
Visit official siteFrom the air
Seventy percent of Kauai has no road.
Waimea Canyon, the Na Pali fluted cliffs, hidden waterfalls. A helicopter, ideally doors-off, is how you actually see the island.
Doors-off
Lihue & Princeville
Jack Harter Helicopters
The originator of Kauai helicopter touring since 1962, with a dedicated doors-off flight for unobstructed photography.
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Lihue
Blue Hawaiian Helicopters
Hawaii's largest operator, an EcoStar fleet, FAA Diamond certified every year since 1998, with synced in-cabin narration.
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Lihue
Mauna Loa Helicopter Tours
Boutique, doors-off at no extra cost, with a private two-to-three passenger Kauai experience: the lowest-density option.
Visit official siteDoors-off
Lihue
Air Kauai Helicopters
Small-operator doors-off and doors-on circle-island flights with strong reviews and open-air photography.
Visit official siteThe table
Sunset tables and farm-to-fork chefs.
Kauai's dining runs from oceanfront icons to North Shore wine rooms and true farm dinners. We hold the hard reservations.
Iconic
Poipu
The Beach House
Kauai's most iconic oceanfront sunset table, Pacific Rim cuisine served right at the water's edge.
Visit official siteAward-winning
Poipu
Merriman's Fish House
Chef Peter Merriman's farm-to-table flagship at Kukui'ula, sourcing more than ninety percent local.
Visit official siteAward-winning
Poipu
Tidepools at Grand Hyatt
Thatched bungalows over a koi lagoon at a waterfall's base, named a top hotel restaurant in America for 2025.
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Hanalei
Bar Acuda
The North Shore tapas-and-wine institution from Jim Moffat, a former Food & Wine Top New American Chef.
Visit official siteAward-winning
Poipu
Red Salt
Frequently cited as Kauai's finest restaurant, a Kauai-native chef cooking local seafood at Ko'a Kea.
Visit official siteTop rated
Koloa
Eating House 1849
James Beard winner Roy Yamaguchi's plantation-era eatery at The Shops at Kukui'ula.
Visit official siteFarm dinner
Kilauea
Common Ground
A four-course, in-season dinner served on a working North Shore farm, with lei-making before you sit.
Visit official sitePrivate chef
In your villa
Kauai Ono (private chef)
Chef Justin Smith brings true farm, fish, and forage private-chef dinners into your villa or residence.
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Private group retreat
Let’s design it around you.
Share what you can already picture. A concierge fills in everything still open and sends back a plan, not a quote.