Wailea, located in South Maui, is known for its luxurious resorts and golf courses. Its golden beaches and gorgeous water boast spectacular sunsets and have been drawing visitors for decades. Relaxation and adventure await you at this island destination. Carve out your slice of paradise with this three-day itinerary the entire family will love.

Day 1

9:00 a.m. | It’s island time. Fuel your day at 5 Palms, located right on the water and boasting a stunning ocean view. You can’t go wrong with any of their specialty benedicts—and satisfy the sweet tooth with their 5 Palms Baked Pancake, topped with caramelized bananas, macadamia nuts, and coconut butter. 

11 a.m. | Soak up the sun! Kids—and kids at heart—will enjoy the Grand Wailea’s famous Canyon Activity Pool, nine pools linked together by a lazy river outfitted with waterslides, rapids, and even a rope swing. When you’re ready for relaxation, the elegant adults-only Hibiscus Pool is your romantic, quiet escape.

2 p.m. | Take a break from the sun while wandering The Shops at Wailea. From fine art and jewelry to designer and clothing shops galore, you’ll find something for everyone—including souvenirs to take back home.

5 p.m. | Live the island life enjoying live music during happy hour at Mokeypod Kitchen. Featuring drink specials and half-off appetizers, you can’t go wrong. For a true taste of Maui, order the Monkeypod Mai Tai, topped with lilikoi foam.

7 p.m. | Make it a date night with dinner at Mama’s Fish House. Take in the sunset with impeccable ocean views and dine on the catch-of-the-day amongst the Polynesian décor and tropical breezes.

Day 2

6:30 a.m. | Rise and shine—you’re in for a day of excitement with the Trilogy Discover Lanai sailing excursion. Sail to the Hulopo’e Marine Preserve off the coast of Lana’i where you’ll swim with tropical fish and sea turtles, cruise alongside dolphins, and watch for humpback whales. Enjoy home cooked meals served on board, including Mom Coon’s famous cinnamon rolls, fresh tropical fruits, and a BBQ lunch. Sip on a mai tai on the ride back and soak in the sight of the island from the water.

3 p.m. | Return to your residence sun kissed and satisfied after your long day of boating. Rinse off with a dip in the Grand Wailea pools just a short jaunt away.

6 p.m. | Leave the cooking to the professionals as Chef Hiram Peri prepares dinner for the family in your residence. Dine al fresco on your spacious lanai and take in the sunset as it dips below the horizon, signaling another day well spent.

Day 3

9 a.m. | Start your day with breakfast at Nalu’s South Shore Grill. For a classic Hawaiian favorite, order the Loco Moco—a local ground beef patty over brown rice topped with homemade gravy and two eggs any style.

11 a.m. | Take in a different view of the island with a drive to Iao Valley. Paved and unpaved nature trails beckon you to meander through the valley, taking in the sights of jagged peaks, lush rainforest, and a rainbow of tropical plants.

3 p.m. | Wind down from your adventure of the day with a treatment at the Spa Grande at the Grand Wailea, voted one of the top 10 spas in the U.S. Indulge in their famed hydrotherapy circuit through various pools and emerge refreshed and relaxed.

6 p.m. | Close out your perfect weekend with dinner at renowned Merriman’s Restaurant, featuring farm-to-table delicacies served with ocean views. Enjoy an extensive wine list and locally sourced menu items showcasing the bounty of the islands.

Stay

Located in the gated community of Ho’olei, The Club's stunning three-bedroom residences are the quintessential Hawaiian retreat. The homes are just a short walk to the Beach Club featuring a fitness center and pool, and across the street from the Grand Wailea and Wailea Beach, where you can enjoy snorkeling, swimming, and beach lounging.

In the residences, luxurious contemporary décor and comfortable open floor plans embrace families in style. A gourmet kitchen leads to dining for six and a large living room surrounded by pocket glass doors. Open them wide to take advantage of the enormous outdoor lanai that provides additional dining, seating, and a grill. The ocean view expands out beyond the resort and is ideal at sunset. Here, the amenities of the world-class Grand Wailea are right next-door, including upscale boutiques and trendy restaurants, three championship golf courses, and the world-class Spa Grande and fitness center.