Looking for a luxury semi-tropical island getaway in the United States? Look no further than Maui. While each of the seven main Hawaiian Islands have special qualities, Maui offers the best combination of these qualities – luxurious resorts, excellent restaurants, beautiful scenery, and stunning beaches. Maui also offers an endless array of activities, including helicopter tours, hiking, ziplining, and golf. For watersports lovers, you will find exceptional snorkeling and scuba diving, world class surfing, windsurfing, kite boarding, sailing and deep-sea fishing. Although not known as a food destination, Maui is home to many excellent restaurants serving creative regional and international cuisine using super-fresh local fish and produce.
For this ultimate weekend getaway, we recommend the recently rennovated Four Seasons Resort Maui at Wailea for its luxurious accommodations, stunning setting and top-notch service. To make the most of this weekend, we suggest an ocean-view suite on the resort’s Club Floor. Although the resort is large (over 380 rooms, including 75 suites), the Club Floor offers a much more personalized experience – you have access to a dedicated concierge and there is a private lounge that offers an endless supply of snacks and drinks throughout the day.
The Four Seasons resort, located in the Wailea resort community along the southern coast of Maui, overlooks one of the most beautiful beaches on Maui. With three pools, including an adults-only infinity pool overlooking the ocean, a fabulous spa, a well-equipped fitness facility and a water sport center located on the beach, there is no shortage of activities. The Four Seasons also has three excellent restaurants, including Wolfgang Puck’s Spago, a steakhouse and an Italian restaurant.
The Four Season’s brand is known for top-quality service and here you will find the staff to be very friendly and helpful – smiles abound. To make the most of your visit, take advantage of the excellent concierge desk, overseen by Maui-native Sam Wilhelm. Not only will they take care of your weekend’s dining reservations and activities, they offer curated once-in-a-lifetime experiences called “Unforgettable Experiences”. These include luxury helicopter trips to Hana Ranch, a helicopter trip to a coffee plantation on the Big Island, and a whale watching tour with top underwater photographers (see Final Thoughts for more details of these extraordinary experiences).
Four Seasons Resort Maui at Wailea // 3900 Wailea Alanui Drive, Wailea // website
To get a sense for Maui’s geological diversity and truly appreciate the island’s beauty, start your luxury weekend with a helicopter tour of the entire island with Sunshine Helicopters. The full island tour will take you to the top of Haleakala’s magnificent crater, across the triple-canopy forests on Maui’s south side and over Maui's most remote southern coast with views of the town of Hana, the Seven Pools and fabulous coastline waterfalls. Heading north, you will fly over West Maui, which is home to one of the wettest places on earth. You will fly into verdant green valleys and pass streaming waterfalls, including the Wall of Tears with over 17 waterfalls flowing at once and the 1,100-foot Honokohau Falls, Maui’s tallest waterfall. Finally, you pass over the resorts of Kaanapali, Kapalua and the old whaling village of Lahaina on the way back to the airport.
Sunshine Helicopters // Kahului Heliport - Hangar #107 // website
Not far from the heliport is Pa’ia, an eclectic Hawaiian town with a hippy/hipster/surfer vibe. Here you will find good restaurants, lots of surf shops, cute boutiques and art galleries. Be sure to visit the Cesere Brothers’ gallery to see their dramatic underwater photos.
Cesere Brothers // 83 Hana Hwy, Pa’ia // website
Just down the Hana Highway from Pa’ia is the world famous Hookipa Beach, the best windsurfing and kiteboarding spot in Maui. Make sure you visit this beach to see some of the world’s best windsurfers and kiteboarders leaping high in the air and riding the large waves at this dramatic spot.
For lunch, we suggest Mama’s Fish House, a very popular beach-front restaurant with spectacular ocean views located just outside of Pa’ia. Mama’s has been around for years and the Polynesian tiki décor is somewhat reminiscent of Trader Vic's. While the restaurant is very expensive, the quality of the fish is excellent -- the restaurant prides itself on the provenance of its ingredients and even lists on the menu the fisherman who caught the fish. Although a little kitschy and catering to the tourist trade, it is one of the best fish restaurants on Maui.
Mama’s Fish House Restaurant and Inn // 799 Poho Place, Pa’ia // website
For a casual alternative, we love Leoda’s Kitchen and Pie Shop, a small casual restaurant located along road to Lahaina and West Maui that offers simple sandwiches, burgers and salads using locally sourced ingredients. The real draw, however, are their amazing single-serving pies – especially the key lime, pineapple macadamia nut, coconut cream and banana cream pies. Make sure you try one of their pies while on Maui!
Leoda’s Kitchen and Pie Shop // 820 Olowalu Village Rd., Lahaina // website
We suggest spending the afternoon exploring West Maui’s stunning beaches. Our favorite West Maui beaches include Kaanapali Beach, with its three miles of white sand and crystal clear water, Kapalua Bay Beach, a smaller beach that is excellent for snorkeling, swimming and sunbathing, and Napili Beach, a beautiful small crescent of white sand and good for swimming, sunbathing and body surfing.
After an afternoon at the beach, head down the highway to the historic whaling town of Lahaina. Here you will find an active harbor and well-preserved historic buildings (also, for what it’s worth, the largest banyan tree in the U.S.). While worth a short visit, be aware that much of Lahaina’s original charm has been replaced by galleries selling kitschy art and tourist shops selling t-shirts and souvenirs.
For dinner in West Maui, we love Merriman’s Kapalua. The restaurant is located on a spit of land overlooking the beautiful Kapalua Bay and is one of the best places in Maui for sunset cocktails or dinner (make sure you time your reservation to coincide with the sunset). The menu focuses on local fish and produce grown by Maui’s best farmers. Standouts include a “pupu” taster plate of bite-size portions of their signature appetizers and their Macadamia Nut Crusted Mahi Mahi. Save room for their decadent desserts, especially their Maui Golden Pineapple and Macadamia Nut Bread Pudding with butter rum sauce. Delicious!
Merriman’s Kapalua // One Bay Club Drive, Lahaina // website
Maui is known for its extraordinary aquatic adventures. For this morning, we suggest either a whale watching excursion (during whale season) or a scuba diving/snorkeling trip to a spectacular coral reef off the coast of Maui.
If you are visiting Maui between December and March, we recommend booking a whale watching excursion. Each winter, humpback whales make their annual migration from Alaska to the Hawaiian Islands for mating and giving birth to calves. Of all the Hawaiian Islands, you will find some of the best whale watching in Maui since the whales congregate in the channel just off the coast. Although the whales can be spotted from shore, the best way to see these massive mammals is on the water. We recommend arranging an excursion with one of the tour companies that use small pontoon boats since they can travel quickly to areas where the whales are spotted and they afford great viewing (though, by law, the boats cannot get closer than 100 feet from the whales).
In addition to spotting whales, if you are lucky, you might be joined by a pod of dolphins that will follow right next to the boat and often give a show with flips and leaps into the air.
The Hawaiian Islands are a diver’s and snorkeler’s paradise with warm waters, excellent visibility, and large coral reefs teeming with vibrant tropical fish and giant turtles. One of the best snorkeling and dive spots in Hawaii is Molokini Crater. This crescent-moon shaped crater is located off the coast of Maui and offers a shallow aquarium-like underwater amphitheater filled with schools of beautiful tropical fish. It is a perfect spot for snorkelers and beginning divers. For advanced divers, the back wall of Molokini Crater offers an amazing drift dive, with the wall dropping off to more than 360 feet and the opportunity to spot bigger fish, like manta rays, sharks and schools of jacks. Other excellent dive sites include Lanai’s Cathedrals and Sharkfin Rock.
For lunch, Ferraro’s Bar e Restorante, a casual al fresco restaurant at the Four Seasons Resort, is a good option. The restaurant overlooks Wailea Bay and offer salads, sandwiches, pasta and stone cooked pizza.
Another casual option not far from the resort is Peter Merriman’s Monkeypod Restaurant. Here you will find tasty sandwiches, fish tacos, salads and pizzas from wood-fired pizza oven in a casual atmosphere.
Monkeypod Restaurant // 10 Wailea Gateway Place, Kihei // website
For those looking for an active afternoon, there are many options. For golfers, there are three excellent golf courses in Wailea – including two Robert Trent Jones II courses. For water lovers, the hotel’s beach activity desk can set you up with sailboats, kayaks or stand-up paddle boards. If you are lucky, you may encounter a playful pod of dolphins or get a close-up of a humpback whale.
If you are looking for relaxation, spend the afternoon at a poolside cabana or under an umbrella at the beach. For the ultimate relaxation, book a signature lomilomi massage, which is the traditional Hawaiian massage involving long strokes, at the resort’s serene spa.
For tonight’s dinner, we recommend Ka’ana Kitchen, which is the signature restaurant at the Andaz Maui at Wailea. The cheery restaurant, known for its regional Hawaiian dishes served family style, has an open kitchen in center of the main dining room, though we prefer the outdoor deck overlooking the pools and the ocean (especially at sunset). The farm-to-table menu is thematic and features top-quality ingredients from local fisherman, farmers and ranchers. Some of the highlights from a recent dinner included XO Kauai Shrimp with tomato jam, anchovy aioli and Japanese eggplant, Bigeye Ahi with kabocha squash and pickled ogo (a type of seaweed) and just-caught local fish with corn and sweet pea purée.
Ka’ana Kitchen // 3550 Wailea Alanui Drive // website
One of the most memorable experiences of any Maui visit is the 64-mile Road to Hana. This full-day trip takes you along some of the most beautiful scenery in the world. You will pass lush green rain forests, towering waterfalls, a dramatic coastline and beautiful beaches, including the unique black sand beach at Waianapanapa State Park. The road eventually leads to the town of Hana, a small town that seems far removed from the bustle of modern life.
Given that the restaurants in Hana are mediocre at best, before you leave, arrange to have your hotel pack a picnic lunch to enjoy at one of the spectacular beaches along the way. You can also stop at one of the many roadside stands along the Hana Highway to purchase banana bread, fruit and grilled food. With over 600 turns, many one-lane bridges and amazing vistas, be prepared for a slow drive (note that it helps to start early so you are not stuck behind a train of cars). The scenery on the Road to Hana is truly spectacular – an experience not to be missed.
For your last night’s dinner, we recommend the Restaurant at Hotel Wailea, Maui’s first Relais & Chateau restaurant. The romantic restaurant offers an Italian-influenced menu featuring locally grown organic produce and locally caught fish. The restaurant offers an excellent wine list and is a recipient of 2016 Wine Spectator’s Award of Excellence. Some of our favorite dishes included Maui-grown tomatoes with burrata, Kampachi crudo with avocado purée and green papaya, and local red snapper with sauce vierge. For dessert, don’t miss their decadent molten lava cake with toasted s’mores. For a very special experience, book the “Treehouse” where you will enjoy a 5-course dinner prepared by a private chef in private treehouse-like setting with stunning ocean views.
Restaurant at Hotel Wailea // 555 Kaukahi Street // website
There is so much to see in Maui that you will need to rent a car to fully explore the island. To take advantage of the semi-tropical weather and make the most of your explorations (especially the Road to Hana), we highly recommend renting a convertible.
When booking a helicopter tour, although more expensive, we recommend booking the front seats on a EchoSTAR helicopter (sometimes called WhisperSTAR). These helicopters offer better viewing than the less-expensive Astar helicopters. Note that while there are numerous excellent helicopter services, for an extra fee, Sunshine Helicopters will allow you to reserve the front seats (subject to weight and balance requirements).
Four Season’s "Unforgettable Experiences"
The Four Seasons Resort has curated a handful of once-in-a-lifetime experiences. For an incomparable day, you can arrange for their “Taste of Island Life” adventure, where you will be taken by helicopter from the resort to Hana Ranch, where you will met by the ranch staff and offered to take a behind-the scenes tour of the ranch and garden, bike through the town of Hana, or take a guided hike to secret beaches. You will then return to the ranch for a multi-course lunch prepared by Four Seasons Executive Chef and Hana Ranch Chef served in the ranch’s picturesque farmhouse and accompanied by a bottle of wine hand-selected by a Four Seasons sommelier.
Other Unforgettable Experiences include trekking across off-the-grid terrain to capture images of Maui’s legendary King’s Highway with a professional photographer; a bean-to-cup Kona coffee tour at a stunning private estate that included an aerial tour of the fiery display of Kilauea Volcano on the way home to Maui; and a whale-watching adventure with underwater fine-art photography duo, the Cesere Brothers.
Four Seasons Resort’s Unforgettable Experiences // website