Destination Guides

Living and Vacationing in the Hawaii Islands

With a favorable climate, beautiful scenery, and world-class golf, the Hawaii islands make the ideal location for a luxury vacation, or second home

The name “Sandwich Islands” doesn’t have such an exotic ring to it, does it? But that’s how the Hawaii islands were once known thanks to James Cook, who visited them in 1778, and chose the name to honor John Montagu, 4th Earl of Sandwich and the then First Lord of the Admiralty.

The archipelago’s now familiar name comes from its biggest island, Hawaii. Various theories exist about the origin of this name – it is possibly a mixture of “Hawa” and “li” which translates as small, or new, homeland. Hawaii today consists of eight major islands and 124 smaller ones, numerous atolls, and smaller islets. The archipelago spans 1,500 miles, from the Kure Atoll in the north to the island of Hawaii in the south.

Says, Zackary Wright, Executive Director, Western North America & Asia Pacific Regions at Christie’s International Real Estate, “From the mystical beauty of Kauai’s emerald valleys, and the geological wonderland that is the Big Island, to the towering surf along Oahu’s North Shore, Hawaii is truly America’s Paradise. Its unparalleled natural beauty combined with its rich multicultural traditions make Hawaii the choice of those who have the option and the means to live anywhere.”

Kailua-Kona, Hawaii, is renowned for its outdoor activities and watersports, but you can also enjoy coffee-tasting, a visit to the farmers' market, and tasting local beer from the Kona Brewing Company. Photograph: Hawaii Tourism Authority/Tor Johnson. Banner image: Maui leis for sale. Photograph: Hawaii Tourism Authority/Tor Johnson Photography
Kailua-Kona, Hawaii, is renowned for its outdoor activities and watersports, but you can also enjoy coffee-tasting, a visit to the farmers' market, and tasting local beer from the Kona Brewing Company. Photograph: Hawaii Tourism Authority/Tor Johnson. Banner image: Maui leis for sale. Photograph: Hawaii Tourism Authority/Tor Johnson Photography
Mention Hawaii and, for many, the images that come to mind are of tropical landscapes, endless beaches, azure seas, and beautiful girls draping floral leis around the necks of arriving visitors. Add to this an average annual high temperature of 84.5°F (29°C) and some of the world’s most desirable real estate, and it’s easy to see why you might want to spend time – or set up home – here.

Rod Easterly, Broker in Kauai of Hawaii Life Real Estate Brokers, an affiliate of Christie’s International Real Estate, perfectly sums up the appeal of the islands: “I love Hawaii because it’s the most remote land mass on the earth, yet we still get to enjoy the benefits and security of being a US state. Additionally, the people who live here are among the healthiest in the country because of the laid-back lifestyle and easy access to beautiful weather and outdoor activities.”

The people who live here are among the healthiest in the country because of the laid-back lifestyle

For your next visit, here’s what you need to know about life in paradise:

HAWAII, THE BIG ISLAND
As its name indicates, Hawaii is the largest island in the archipelago. It is also the youngest – home to active volcano Kilauea and historic park Puuhonua o Honaunau. Lovers of sand and surf shouldn’t miss the famous black-sand beach and extensive snorkeling and diving opportunities. Foodies are equally well catered for, with some 350 dining options to choose from. Upscale restaurants include seafood hotspot Huggo’s in Kona, and Merriman’s in Waimea that serves top-quality regional cuisine. Merriman’s is the signature restaurant of Peter Merriman, one of the 12 chefs who founded Hawaii Regional Cuisine (HRC), a style of cooking that celebrates the fusion of local Hawaii ingredients and the islands’ diverse ethnic influences. Looking for a place to stay? Try the exclusive Four Seasons Hualalai, set on the Kona-Kohala Coast, a showpiece oceanfront luxury resort, complete with oceanside infinity pool and 18-hole golf course.

The exclusive Four Seasons Hualalai's infinity pool reflects the luxury of the entire resort, with breathtaking ocean views, island-style decor, and attentive poolside service. Photograph: Four Seasons/Don Riddle.
The exclusive Four Seasons Hualalai's infinity pool reflects the luxury of the entire resort, with breathtaking ocean views, island-style decor, and attentive poolside service. Photograph: Four Seasons/Don Riddle.

ON THE MARKET ON THE BIG ISLAND
Carrie Nicholson, of Hawaii Life Real Estate Brokers, an affiliate of Christie’s International Real Estate, describes one her spectacular homes on the big island as “One of the most beautiful contemporary homes that I’ve ever seen from the finishes, features and details. Nothing has been missed in this exceptional residence”.

Adds Nicholson of another spectacular property, “Walk out on the emerald green course of hole 8 to hit a few balls from the back yard of this beautiful home at Kukio.”

OAHU
“The Gathering Place,” as Oahu is known, is the third largest island and is home to Honolulu, the island’s state capital – and also the 11th largest metropolitan area in the US. The city is the gateway to the island, and its famous Waikiki neighborhood – with its palms, high-rise hotels, and views of volcanic Diamond Head in the distance – is the go-to destination for shopping and fine dining.

Hawaii’s contemporary food scene is spearheaded by Oahu, which is home to star chefs, family-run local eateries, multi-ethnic offerings, and bountiful farmers’ markets. Head to Waialae Avenue in Honolulu’s Kaimuki neighborhood for sheer choice. Here you can find, among other things, a Chinese bakery, Italian bistro, Mexican food, dim sum, and HRC favorite 3660 on the Rise. Other Honolulu culinary highlight’s include HRC pioneer Alan Wong’s eponymous restaurant, and Vintage Cave, where chef Jonathan Mizukami delights diners with a combination of local ingredients and high-end French fare – it’s here Barack and Michelle Obama chose to dine on New Year’s Day 2015, during their visit to Hawaii.

Oahu is home to around 955,000 people, with approximately 81% of those living on the "city" side of the island. As a result, the Honolulu housing market is booming, with homes priced at roughly three times more than the average home in the United States. Photograph Hawaii Tourism Authority/Tor Johnson
Oahu is home to around 955,000 people, with approximately 81% of those living on the "city" side of the island. As a result, the Honolulu housing market is booming, with homes priced at roughly three times more than the average home in the United States. Photograph Hawaii Tourism Authority/Tor Johnson

ON THE MARKET IN OAHU
Choi Realty, an affiliate of Christie’s International Real Estate, is currently marketing spectacular homes on Oahu. Below is a selection of three.

1. Hokua, 1288 Ala Moana Boulevard, Honolulu
This move-in-ready, two-story penthouse offers unobstructed 180° views, and interiors that span more than 7,000 square feet. Stand-out features include a 2,800-square-foot private recreation/entertaining area and rooftop deck. The Honolulu home offers resort-style amenities in the ultimate location – across the street from the beach and just one block from Ala Moana Shopping Center, the world’s largest open-air mall.
$28,888,000

2. 828 Moaniala Street, Honolulu
Designed and built by Entertainment Tonight creator and TV producer Al Masini, this two-story hillside home offers sweeping mountain and ocean views – the neighboring islands of Molokai, Maui, and Lanai are visible on most days. With five bedrooms and seven baths, the property also features a media room/home theater, gym, spa, and staff quarters. There is also a large master suite with ocean and mountain views.
$13,800,000

3. 4432 Kahala Avenue, Honolulu
This custom-built, two-story home, completed in 2015, is located on Honolulu’s most expensive street, with beach access right across the road. The property boasts four bedrooms, a gourmet kitchen with a large island and custom breakfast booth, a guest suite with a separate entrance, and a gym (or fifth bedroom) with a sizeable steam room/shower. There is also an outdoor pool with a pavilion and a three-car garage with a gated driveway.
$10,800,000

LANAI
The smallest publicly accessible inhabited island of the chain is Lanai, which is also known as “Pineapple Island,” thanks to the many plantations that covered it in the past. Lanai is very popular with walkers and hikers, but it is golf enthusiasts who will find most to love about the island, as it boasts two world-class courses. The Koele Golf Course is an 18-hole championship course designed by legends Greg Norman and Ted Robinson, surrounded by soaring pines and eucalyptus trees. Jack Nicklaus’s Manele Golf Course, meanwhile, spans several hundred acres of natural lava outcroppings. Manele is considered one of the most difficult courses in the world, with three holes that are actually located on ocean cliffs. Visitors should note that much of Lanai is accessible only by four-wheel drive, and that there are no traffic lights on the island.

Jack Nicklaus's Manele Golf Course is a challenging open oceanside course that is dictated as much by the prevailing winds as it is by a golfer's skill. Photograph: Lanai/Manele Hawaii Tourism Japan
Jack Nicklaus's Manele Golf Course is a challenging open oceanside course that is dictated as much by the prevailing winds as it is by a golfer's skill. Photograph: Lanai/Manele Hawaii Tourism Japan

MAUI
Maui, known as the “Valley Isle,” is considered the most bohemian of the islands. Dotted with artistic communities and quaint towns, it was, for many years, voted “Best Island” by Condé Nast Traveler. Explore the wooden shopfronts around Market Street in the center of Wailuku, the island’s main town, or learn about Maui’s history at the Bailey House Museum, which showcases Hawaii artifacts alongside 19th-century missionary objects, koa furniture, and paintings of Hawaii by Edward Bailey. Also worth a visit is historical whaling town Lahaina – Moby Dick author Herman Melville once took ship leave here. Lahaina today boasts galleries and boutiques, as well as historical tourist sites such as US Seamen’s Hospital and Hale Paaho (Lahaina Prison).

Opened in 1928 and renovated in 1995/6, Wailuku's Spanish mission-style Iao Theater is home to the Maui Onstage live theater group. Photograph: Hawaii Tourism Authority/Tor Johnson Photography
Opened in 1928 and renovated in 1995/6, Wailuku's Spanish mission-style Iao Theater is home to the Maui Onstage live theater group. Photograph: Hawaii Tourism Authority/Tor Johnson Photography

ON THE MARKET IN MAUI

KAUAI
Small but simply perfect as an island escape, Kauai is a dream for lovers of outdoor pursuits – kayaking on the Wailua River, hiking the trails of Kokee State Park, and ziplining above the many lush valleys are just some of the activities you can enjoy here. The island is also home to the beautiful National Tropical Botanical Garden. The three gardens here (there are five in total – the others are in Maui and Florida) showcase unique collections of plants gathered from around the tropical world. One garden is located in the north of the island, the other two in Kalaheo, on the southwest edge of the island.

“I love Kauai, in particular, because you can explore nine different climate zones inside of two hours,” says Hawaii Life’s Rod Easterly. “Kauai is 650 square miles and I can go from rainforest (where I live) to desert within one and a half hours. Kauai has the only navigable river in the state of Hawaii. Kayaking, SUPing (stand-up paddle surfing), boating, and exploring the waterfalls along the rivers and streams are highly recommended. The soul of Kauai, in my opinion, is Kalalau Valley, which can be accessed only by boat or by hiking an 11-mile coastal trail that passes 1,000-foot waterfalls and green mountain spires that take your breath away.”

Hanalei town, on Kauai's north shore, is home to interesting historical sites and art galleries, while Hanalei Bay is considered to be one of the best beaches in all of Hawaii. Photograph: Hawaii Tourism Authority/Dana Edmunds
Hanalei town, on Kauai's north shore, is home to interesting historical sites and art galleries, while Hanalei Bay is considered to be one of the best beaches in all of Hawaii. Photograph: Hawaii Tourism Authority/Dana Edmunds

ON THE MARKET IN KAUAI  

Brydeswood Ranch
In Kalaheo, a CDP (census-dedicated place) of just three square miles, Hawaii Life is marketing the unique Brydeswood Ranch – 23 subdivided lots ranging from four to 17 acres, offering a total density of 84 home sites, all being sold together. Among the lots on offer is the Manager’s Stone House, one of the oldest homes on the island. With five bedrooms and four baths, the home is the perfect place from which to enjoy the sunset. The property is within easy reach of local beaches as well as Olu Pua Gardens and the National Tropical Botanical Garden.
$13,000,000

If you enjoy a diverse mix of cultures, year-round warm weather, beautiful scenery, and high-end shopping and eating, then Hawaii is the destination for you – whether it be for a relaxing vacation or to buy a property.