Your Personal Wailea Guide
While we love all the distinct areas of Maui for different reasons, Wailea holds a special place with its perfect gold sand beaches, prime sunset views and gorgeous scenery. Let’s take a closer look at what makes Wailea so special, from the land’s cultural significance, great restaurants, stunning resort properties, popular activities and real estate.
South Maui History
Wailea
According to legend, Lea, the Hawaiian goddess of canoe builders, was transformed into ‘elepaio, or forest bird, and would fly over the shoreline of South Maui. This area became known as Wailea, or “Waters of Lea”. Ancient Hawaiians grew sweet potatoes and lived in modest fishing hales (houses) here until the 1848 Great Mahele Land Redistribution Act by King Kamehameha III led to cattle raising as the dominant use and eventual formation of the Ulupalakua Ranch. During WWII, Wailea became a training area for the Marines in the Pacific Theater and in 1971, Alexander & Baldwin partnered with Northwest Mutual Life Insurance Company of Milwaukee to begin building a residential resort community. Today, Wailea boasts more than 2,000 homes and condos, 5 resorts and 3 world-class golf courses.
Kihei
Legend has it that two clouds once battled along the upper slopes of Haleakala volcano. The battle continued until both sides decided to call a truce, and the resulting space of blue sky was called Alanui o Lani, or the “Highway to Heaven”. Previously called Kama’ole, meaning “barren”, Kihei didn’t become a tourist destination until the mid 1970s and 80s, when condos, shopping centers and strip malls slowly made their way in. Today, Kihei is among one of the top Hawaiian destinations, famous for its laid-back attitude, gorgeous beaches and unforgettable South Maui sunsets.
Makena
Meaning the “Land of Abundance and Plenty”, Makena holds historical significance for its many ancient fishing ponds and sacred Hawaiian temples, or heiau. After Captain James Cook discovered this area of the island, it became a bustling seaport for sweet potatoes and other produce. When severe drought forced closure of the sugar mill and plantation, the Rose Ranch was sold and renamed Ulupalakua Ranch, and Makena became the main port for trading and shipping cattle. In 1855, the Keawala’i Church was built from lava rocks and crushed coral, which is still in use today. During WWII, the trading port at Makena Landing was closed down and the area was used for military training and exercise. Today, Makena is home to one resort, the Makena Beach and Golf Resort, and is a popular place for spectacular beaches, including Big Beach and Little Beach, and a favorite resting place for Hawaiian Spinner Dolphins at the nearby La Perouse Bay.
Wailea Restaurants
Wailea is home to some of the best restaurants (with the best views) on the island, including those in and around some of the most popular resorts. Don’t come to South Maui without trying these Wailea specialties!
Ferraro’s Bar E Ristorante: Located at the stunning Four Seasons Resort in Wailea, Ferraro’s is the only open-air beachside restaurant in the area. Enjoy spectacular sunset views with Italian-inspired menu items like the Ricotta Gnocchi with Red Wine Braised Short Rib Ragout and Tagliatelle with Manilla Clams and Shallots. The kiawe wood-burning oven sets the stage for authentic taste and ambience. Go for dinner and enjoy live Italian music from 6:30 to 9:30pm.
DUO Steak & Seafood: Also located at the Four Seasons Resort, head to this poolside restaurant for award-winning chef creations like the Pork Belly Buns with Lilikoi Chili Sauce, New York Strip with Maui Onion Pineapple Chutney, or Lobster Crusted Salmon with Shishito Peppers, Venus Rice and Miso Vinaigrette. For a less formal affair, try their assortment of Breakfast Buffet items from 6:30am to 11:00am. Call early to reserve the private dining room near the waterfall pool for dinner with a view.
Joe’s Restaurant: Located above the Wailea Tennis Club, Joe’s is the low-key, American comfort food option from local chef favorites Bev and Joe Gannon of the Hali’imaile General Store and Gannon’s Restaurant. Try the Tequila Steamed Clams with Roasted Bell Pepper Sofrito and Spicy Pork Sausage, Chicken & Waffle BLT with Maple Syrup Bacon or Joe’s Favorite Meatloaf with Citrus Barbeque Sauce for a delicious twist on old favorites. Grab a Kona Mud Pie and Chocolate Martini for dessert and thank us later.
Capische?: Nestled in the beautiful Hotel Wailea, Capische? takes on Italian fine dining with classical French techniques. With a strong belief in sustainability and local ingredients, don’t miss the Quail Saltimbocca with Apple-Smoked, Bacon-Wrapped Quail, Mushroom Truffle Risotto with White Truffles, Summer Truffles and Oyster Mushrooms or the Porcini Crusted Ahi with Pumpkin Seed Vanilla Vinaigrette. Grab a table on the lanai, romantic garden or experience Il Teatro with your own personal chef and specialized menu.
Gannon’s: From the same creators of Joe’s comes Gannon’s, offering some of the best food and views on the island with floor to ceiling glass doors and culinary treats like the Raw Bar, Makai (“Towards the Sea”) specials like Lobster Shellfish Paella, Mauka (“Towards the Land”) specials like the Hawaiian Salt Crusted Ribeye, and Desserts like the Creme Brulee Trio of Brown Sugar Ginger, Lilikoi and Butterscotch. Check out the Red Bar for delicious specialty cocktails and daily Happy Hour from 3:00 to 8:30pm.
Morimoto Maui: Best known for Iron Chef and Iron Chef America, celebrity chef Masaharu Morimoto is the Executive Chef at Morimoto, the beautiful new restaurant at the Andaz Maui at Wailea. Blending Western and Japanese traditions, Morimoto offers the best and freshest hand-rolled sushi and sashimi, including specialties like the Oh-Toro, or Fatty Tuna, Kani, or King Crab, and Eel Avocado Roll with Barbeque Eel and Avocado. Grab a table on the terrace during sunset for a truly spectacular Maui meal with a view.
Humuhumunukunukuapua’a: Located at the Grand Wailea Resort in a beautiful ocean-side setting under a Polynesian thatched-roof, Humu serves up a mouthwatering assortment of dishes, including the Ma Ke Kai I Ke Kula, a Surf and Turf dish with Grilled Lobster Tail and Filet Mignon, Seared Ahi Loin with Foie Gras Dumpling, Stir Fry Mushrooms and Snow Peas, and Raw Bar Specialties like the Kampachi Poke with Cilantro, Avocado Puree and Smoked Ponzu. Enjoy one of the most romantic dining settings on the island and call ahead for reservations.
Pita Paradise: With two locations in South Maui, Pita Paradise has become the go-to for Greek and Italian cuisine, open daily for Lunch and Dinner. Try the Traditional Greek Salad, Australian Range Lamb with Grilled Pita, Fresh Fish Kabob with Sautéed Veggies, Grilled Pita and Rice Pilaf or Greek God’s Platter with Mousaka, Gyro, Spinach Tiropitas and Tatziki for the best authentic Greek food on Maui. Enjoy their special daily Happy Hour menu from 3:00 to 6:00pm with discounted Pupus, Souvlaki, and Pita Pitza’s.
Monkeypod Kitchen Restaurant: Located conveniently in Wailea with magnificent views of the ocean, head to Monkeypod for delicious cocktails, craft beer, hand tossed pizzas from a kiawe wood-burning oven and cream pies made from scratch. Enjoy the best in locally-sourced ingredients with the Pumpkin Patch Ravioli, Bourgeois Pizza with Big Island Lobster and Hamakua Wild Mushrooms, Organic Macadamia Nut Crusted Mahi Mahi and Bulgogi Pork Tacos with handcrafted Kim Chee. Daily happy hour specials are available from 3:00 to 5:30pm and 9:00 to 11:00pm.
Tommy Bahama Restaurant & Bar: Located in the Shops at Wailea, Tommy Bahama is a well known staple for design, clothing and now cuisine. The large lanai at this Wailea location makes this a wonderful stop for Happy Hour or Dinner, where you can try great local specialties like the Ahi Poke Napoleon with Capers, Sesame, Guacamole and Flatbread, Kona Coffee Crusted Ribeye with Potato Salad and Herb Marrow Butter or Crab Stuffed Shrimp with Sautéed Spinach, Almond Rice and Thai Chili Sauce. Try the Leap of Faith, a specialty cocktail with Tanteo Jalapeño Tequila, Grapefruit, Agave Nectar and Lime.
Longhi’s: Also located in the Shops at Wailea, Longhi’s has been a long-time go-to for the best breakfast dishes on Maui, including Longhi’s French Toast with Grand Marnier-Dipped, Brioche-Style Country Sliced Bread with Mixed Berries, Caramelized Macadamia Nuts and Whipped Cream, Italian Baked Frittata, Fresh Baked Cinnamon Roll and Eggs Benedict with Crab Cakes, Lobster or Smoked Salmon. Start your morning off right with a Mimosa and favorite breakfast item before heading to a beautiful nearby beach!
Wailea Resorts
Whether you’re looking for a romantic pool bungalow in front of an infinity pool or a family-friendly resort with lots of water activities and events, Wailea has it all.
Four Seasons Maui at Wailea: Overlooking the gorgeous Wailea Beach, the Four Seasons is a truly stunning resort, day and night. Featuring the largest rooms and bathrooms on Maui, an attentive staff and luxury amenities that consistently go above and beyond, the resort includes 3 onsite restaurants, an award-winning spa, 3 shopping boutiques, 3 saltwater pools, 4 bars, 3 golf courses, 2 tennis courts and an array of activities that are perfect for families, couples and large groups. Choose from one of the 380 available Guest Rooms and Suites, including 26 Club Rooms and Suites on a special Club Floor. Featuring some of the best restaurants and sunset-views on Maui, the Four Seasons is definitely a beautiful experience for your next trip to paradise.
Andaz Maui at Wailea: Andaz Maui is the newest resort on Maui, and its high expectations were certainly met and exceeded. Designed with a modern interpretation of Hawaiiana, including Hawaiian artifacts alongside modern decor and function, the Andaz offers guests an assortment of 297 Guest Rooms and Suites, including Villas with multiple bedrooms. Three-tiered infinity pools offer sweeping views of the South Maui shoreline at this 15-acre beachfront resort, which also features a full Salon & Spa, 4 full service restaurants and a 24-hour onsite market. Featuring work from local artist Shane Robinson, the Andaz continues to support Maui professionals and commits to adhering to the latest standards in green technology and design.
Grand Wailea: While you may think you’ve arrived in the Las Vegas of Hawaii, we assure you that this magnificently large resort is free of slot machines and full of luxury. Located on 40 acres in front of the beautiful Wailea Beach, the Grand Wailea boasts an impressive 780 Guest Rooms, 52 Suites, the 50,000 square ft. Spa Grande, 4 bars, 5 restaurants, and, perhaps everyone’s favorite part, the Wailea Canyon Activity Pool that consists of 9 pools on 6 different levels. Guests and residents of the nearby Ho’olei Properties also enjoy exclusive access to the best amenities at the Grand Wailea Resort, including the pool, spa and charging privileges at all restaurants. Enjoy the Grand in Grand Wailea at Maui’s most elaborate resort.
Wailea Beach Marriott Resort & Spa: Located between two South Maui beaches, the Wailea Beach Marriott features an impressive infinity pool with overwater cabanas, 3 delicious onsite dining options, including a nightly dinner luau show and local favorites Mala Wailea and MiGRANT, full spa services at the Mandara Spa and shopping at the Shops at Wailea, located only footsteps away. Guests can enjoy lush scenery and gorgeous views, perfect for sipping a cocktail during sunset and relaxing on the beautiful Ulua Beach.
Fairmont Kea Lani: Hawaii’s only all Suite and Villa luxury oceanfront resort, the Fairmont Kea Lani sits on 22-acres of pristine beachfront location in Wailea. Luxurious amenities such as the full service Willow Stream Spa, 3 pools, including an adults-only pool, 4 restaurants, boutique shopping, kid’s club, and water sports on Polo Beach add to the beautiful scenery and decor that have made the Fairmont a favorite for years. Whether you’re looking for a relaxing getaway with a significant other or a family vacation away from the cold weather, the Fairmont offers seclusion and amenities that make it all possible.
Hotel Wailea: While Hotel Wailea doesn’t get the crowds and attention that the other resorts do, that’s exactly what draws most of the guests here. Situated on the hill above most of the other South Maui resorts, Hotel Wailea is a beautiful, no-fuss, well-designed boutique hotel with your relaxation and rejuvenation in mind. From the Japanese-inspired architecture of the lobby to the delicious onsite dining options at Capische? to the amazing scenic views, Hotel Wailea is a perfect choice for those of you who come to paradise to relax while still being pampered. Complimentary transportation to and from the nearest beaches and live music and cocktails are offered weekly in the lobby.
Wailea Activities
No matter what your level of comfortability in the ocean, there’s plenty of activities that will suit your interests in Wailea, South Maui. Get out an explore what makes Maui’s underwater world so unforgettable!
Snorkeling: You can’t make it all the way to Maui without sticking your head in the water. Rent or purchase inexpensive snorkel gear and head to some of Maui’s best snorkeling spots to witness beautiful Hawaiian marine life, from sea turtles to tropical fish and more. We recommend the following areas for South Maui Snorkeling: Ulua and Mokapu Beaches, Polo Beach, Five Caves, the Ahihi Keanau Reserve and La Perouse Bay. For a more memorable and unique snorkeling experience, take a boat charter to Molokini Crater, an ancient volcanic cinder cone atoll, which offers upwards of 180 feet of visibility on good days.
Water Sports: No matter what kind of water sport you’re into (or want to try), Maui has it all. From Outrigger Canoeing to Kayaking, Stand Up Paddle Boarding, Surfing and Scuba Diving, there is no shortage of ocean activities on the Valley Isle. We recommend private canoeing, kayaking, SUP and surf lessons with Hawaiian Paddle Sports. Getting out in the water is a great way to experience the majestic beauty of the island while getting up close and personal to our vast underwater life. From kayaking alongside our local honu at Turtle Town to diving the back side of Molokini Crater, make sure you set time aside to take a dip in the Pacific!
Golf: With 3 world-renowned golf courses, including the Wailea Gold Course, Emerald Course and Blue Course, Wailea attracts thousands of golf aficionados from around the world each year. From the Gold Course, regarded as one of the best-designed courses in the world, to the Emerald Course, which offers incredible ocean views and has won many awards for it’s friendly course and club, to the Blue Course, a typical Hawaiian course with perfectly kept fairways and fantastic views, get ready to step up your golf game in South Maui.
Spas: Above all else, don’t forget to relax! Treat yourself to one of the many luxurious spa treatments at some of the best spas in the country, including the pineapple chardonnay bath, lavender body cocoon and rain massage at Spa Grande at the Grand Wailea, bamboo massage, thai herbal poultice massage and hot stone therapy at the Mandara Spa at Wailea Beach Marriott or the Hawaiian healing wrap with pineapple-papaya polish, rain shower exfoliation treatment and in-ocean, aquacranial massage at Four Seasons Resort Spa at Wailea.
Shopping: For great shopping, head to the Shops at Wailea where you’ll find an assortment of over 70 art galleries, boutiques, shops and restaurants for the whole family. Join Wailea on Wednesdays every 3rd Wednesday of the month for live music and entertainment from 6:30 to 8:00pm. Wailea Gateway Center also offers an assortment of shops, specialty food boutiques and great restaurants.
Wailea Real Estate
Part of what makes Maui so appealing is the wide range of gorgeous real estate. From luxury condos to sprawling estates, check out the latest and best in South Maui real estate.
Ho’olei Condos
With 120 elegant condominium townhomes sitting on 30 acres of flourishing tropical land, Ho’olei is one of the newest additions to the Wailea Resort. This gated Wailea condo community is made up of twenty 2-story buildings, offering 3 different floor plans known as the Plumeria, Hibiscus, and Maile that range from 2,554 to 3,293 square feet in size.
The condos at Ho’olei come with a Grand Wailea Kulana Club membership rolled into the purchase price, which grants it’s members access to the Grand Wailea Resort’s 9 pools, the Spa Grande and the hotel’s fitness center. Kulana Club members are also granted preferred pricing on the Grand Wailea hotel rooms, spa treatments, and food and beverage charged to the member account.
Ho’olei homeowners also enjoy special golf memberships at all three Wailea golf courses, including significantly reduced green fees. The pool at Ho’olei is very impressive. There is a tropical sandy entrance with an amazing 19-foot waterfall. There are also two whirlpool spas, a children’s pool, an outdoor pavilion, a fitness center, private locker rooms, saunas, and shuttle service offered to residents.
Kai Malu
Kai Malu is one of Wailea’s newest and most highly sought after gated communities. The neighborhood consists of 75 duplexes, with 150 residential style homes in total. The entire property sits on approximately 25 acres, located right in the heart of the Old Wailea Blue Golf Course. On-site amenities at Kai Malu include one of the most impressive pool facilities on the entire island, a jaw-dropping 75 foot infinity edge oasis pool with unbelievable views of the 1,500 acre Wailea Resort.
See current listings in South Maui or call Dano Sayles at (808) 870-4899 for more information.
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