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72 Hours: Grand Wailea, Maui

Relaxation or adventure? We combine both in one unforgettable three-day weekend itinerary in Maui, Hawaii.

Given the recent devastation on West Maui and Lahaina — the original capital of the Hawaiian Kingdom — the Club has been closely monitoring travel to Maui. Sadly, many areas and experiences in Lahaina were affected. Yet the Hawaiian tourism board has sent a clear message that one of the best ways travelers can support recovery on Maui is by still visiting and supporting local tourism. South Maui, home to Club residences at Ho'olei Villas at Grand Wailea, is fully operational, and now is an ideal time for a beach escape to its famous grounds. Whether desiring relaxation or adventure, here we combine both in one unforgettable three-day weekend itinerary on Maui.

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

Additionally, please refer to information below for vetted resources to best support Maui. Our Hawaiian ohana (family) is grateful for any assistance sent their way.

What To Do

Day 1

9:00 a.m. | It’s island time. Fuel your day at Akamai Coffee Wailea Village, just a short walk from the Grand Wailea. You can’t go wrong with any of their special brews — and 100% of their coffee is grown on Maui. Satisfy your sweet tooth with their breakfast pastries or go the savory route with avocado toast.

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 memorable souvenirs to take back home.

4 p.m. | Live the island life enjoying live music during happy hour at Monkeypod 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.

Iao Valley
Trilogy Discover Lanai Sailing Excursions

Day 2

6:30 a.m. | Rise and shine — you’re in for a day of adventure 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 Exclusive Resorts home. 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. | Experience 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 luxury wellness 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.


The Club is so thankful our team members on Maui are safe. The Club is offering support by donating to the Maui Fund and encouraging our community to do the same. While Kapalua will remain closed through September, Wailea remains open and encourages visitors to keep their travel plans intact for much-needed tourism revenue to the island.

Interested in making a positive impact?

Please consider donating to the Maui United Way and its Maui Fire Disaster Relief. Immediate needs via fast-tracked grant approvals are sent to existing grassroots organizations that are local and focused on basic needs.  


6 Residences
Maui, Hawaii

Ho'olei Villas at Grand Wailea

6 Residences

Ho'olei Villas at Grand Wailea