Your Day-by-Day Island Guide
We’ve put together these island ideas to help you craft your perfect stay.
DAY 1: Begin Your Stay in Island Leisure
- Rise and shine with an easy stretch in one of our morning fitness classes set in our stunning open-air fitness studio. In between deep, breezy inhales and invigorating yoga poses, make sure to sneak peeks of ocean views drenched in the morning sun.
- Relax in style with some Cabana Downtime. Spend a sunlit afternoon sipping cocktails and soaking up the poolside vibes.
- Watch the sun dip below the horizon at The Birdcage. Enjoy culinary delights from the Japanese Grill, sushi and raw bar, perfectly crafted cocktails and mesmerizing island views.
DAY 2: First, Unwind. Then, Adventure
- Start the day with authentic tastes of Maui: Enjoy a light breakfast at The Restaurant at Hotel Wailea where fresh fare and artisanal island flavors are served in an open-air space.
- Leisure lovers, leave some time to indulge today. Unwind with a soothing lomi-lomi massage and other treatments in the comfort of your suite with our Paradise Retreat offering, including natural, Hawaiian-infused products.
- From leisure to adventure, carry out the remainder of the day with a new and unique perspective — from the seat of a traditional Hawaiian outrigger canoe. Local guides provide guests with a truly authentic Hawaiian Outrigger Canoeing experience along the south Maui coast.
DAY 3: Experience Something New on the Island
- Cultivate inner peace and reawaken your body with a bespoke yoga session in our open-air wellness studio. Looking for something new to try? Spice up your fitness routine (and vacation) and unleash your inner acrobat with an invigorating, private Aerial Yoga experience.
- Experience an island classic—in a classic. Nostalgia takes the wheel as you tool around Maui in a replica 1957 Porsche Speedster with our Vintage Cruising experience.
- Dine within a canopy of mango trees and moonlight at The Treehouse. Coveted as Maui’s best kept secret, our ultra-romantic dining experience is further elevated by intimate service, dazzling ocean views and an exquisite, seven-course, private-chef-prepared dinner. Advanced reservations are required.
DAY 4: A Day on the Shore
- Find your fun in the sun! Let our valets escort you to any beach in the Wailea area, where you’ll enjoy full beach services including lounge chairs, umbrellas, bottled water, and towels. When you’re ready to bounce from leisure to adventure, paddleboards, kayaks, and snorkel gear are also available to rent.
- Catch a wave (or ten!) at Maui’s best breaks with your own private surf instructor in our Surf Safari experience.
- At the end of a sun-drenched day, return to your suite for sumptuous in-suite dining. Stay in and soak up the comforts of your lanai as you’re served award-winning cuisine from The Restaurant at Hotel Wailea.