Maui 8-Day Winter Getaway

Let this trip inspire you, so together we can design your own Remarkable Journey.

Trip Itinerary

Day 1

Arrival Day, Maui

Arrive at Kahului Airport where you’ll be picked up by your private driver and escorted to your accommodations in Wailea, one of the sunniest and driest places on the island. Wailea known for its five beautiful, crescent-shaped beaches and stellar golf courses, is a luxurious resort community in South Maui that spans 1,500 acres of land with staggering ocean views. A stay in Wailea is paradise.

Day 2

Maui’s Lush Rainforests

Awake bright and early and take in your ocean view with room service delivered to your door. Head to the lobby and meet your private driver for the day who will take you to the lush rainforest in eastern Maui for a guided hike, kayaking and a marine life tour. Bring along your swimsuit to take a refreshing dip in the secluded waterfalls and swimming holes after breaking a sweat during your hike. Finish the day back at your resort lounging by the pool and a gourmet dinner from one of the many available restaurant choices in Wailea

Day 3

Beach Day & Helicopter Ride

After yesterday’s activities, you’ve earned yourself some R&R. Rent a cabana and spend the day lounging by the pool or beach. Mix it up with some snorkeling or a yoga class. This afternoon, enjoy a spectacular helicopter flight over southern Maui. Keep your camera out as you fly across beaches, cliffs, and thick swaths of jungle. As you fly over, look straight down into the crater of the dormant Haleakala Volcano, part of Haleakala National Park. Land at a private site near the edge of black volcanic cliffs, with time to snap photos and enjoy the peaceful atmosphere in the gorgeous location. On the trip back to the heliport, fly over canyons, waterfalls, and the lush Hana rainforest before returning to earth.

Day 4

Snorkel Molokini Crater

Today, prepare for an exploration of Maui’s magnificent marine life during a snorkeling experience unlike any other! Head by boat to this long-extinct volcanic crater just off Maui. During the winter and the beginnings of spring, humpback whales are playing in these waters. Once you arrive at the crater, prepare for spectacularly clear waters and diverse marine life as you snorkel in Hawaii’s only island marine sanctuary. After your Molokini snorkeling experience, your boat will cruise along the remote volcanic coastline, where you will see a number of enchanting caves, lava arches and grottos.

Day 5

Maui’s Upcountry Tour

Take in some of Maui’s small-town charm today as your private driver takes you on a tour of Upcountry on the other side of the Island. You’ll be immersed in the food and culture of Upcountry as you visit local eateries, lavender farms, sugar cane mills, botanical gardens and more during this day trip. Enjoy meeting the locals and taking in the less-visited side of Maui.

Day 6

Horseback Riding

Get your cowboy boots ready for today’s adventure. After a nourishing breakfast, your private driver will take you to a secluded hilltop ranch for a private horseback ride. Your cowboy guide will take you along a rugged path that opens to a scenic valley looking out over the Pacific Ocean. Take in the view and the fresh ocean air before heading back to your hotel.

Day 7

Wai’anapanapa State Park

No trip to Hawaii is complete without properly experiencing its volcanic topography. Today your private driver will take you to Wai’anapanapa state park for a truly unique experience. As you arrive, you’ll be greeted by the volcanic black sand beach. You’ll also see striking volcanic features like blowholes and lava tube ponds. Take a dip in the water and enjoy a picnic as you take in the stunning sights.

Day 8

Departure Day

Your driver will meet you at the lobby to take you back to the Kahului Airport. For now it’s time to say a fond “a hui hou”… until we meet again.

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