Here is a sample itinerary for a 7 day visit to beautiful Wailea in southern Maui:
Day 1 – Wailea Beach & Sunset Stroll
Main attraction: Wailea Beach
Ease into island time with a relaxing day at Wailea Beach, near the Four Seasons and Grand Wailea resorts.
Swim and snorkel near the rocks on either end, or rent sea kayaks or paddleboards from Aqualani Sports.
Evening: Walk the Wailea Beach Path for sunset — it stretches along the coastline with stunning views.
Dinner: Monkeypod Kitchen for fresh fish tacos and mai tais!
Day 2 – Snorkel at Molokini Crater
Main attraction: Molokini Crater Snorkeling Tour
Take an early morning catamaran or rafting tour (Trilogy, Redline Rafting).
Snorkel inside the crescent-shaped volcanic crater, then visit Turtle Town to swim with sea turtles.
Afternoon: Chill at the Ho’olei swimming pool area.
Dinner: Tommy Bahama Restaurant in The Shops at Wailea village — try their pineapple martini!
Day 3 – The Road to Hana
Main attraction: Scenic Road to Hana Drive
Start early (6:30 AM). Drive the lush Hana Highway — waterfalls, jungle, black sand beaches.
Must-stops: Twin Falls, Wai’anapanapa Black Sand Beach, and Wailua Falls.
Lunch: Hana Ranch Restaurant.
Return to Wailea by evening, or stay overnight if you prefer a slower pace.
Day 4 – Wailea Golf or Spa Day
Main attraction: Wailea Golf or Resort Spa
Choose between:
Wailea Gold or Emerald Course for world-class golf with ocean views, or
Spa day at the Willow Stream Spa (Fairmont Kea Lani)
Lunch: Gather on Maui in Makena.
- Evening: Enjoy a relaxed dinner at Lineage in the Shops at Wailea village.
Day 5 – Haleakala National Park Sunrise
Main attraction: Haleakala Crater Sunrise
Pre-dawn drive or tour to the summit (~2 hrs from Wailea). Watch the sunrise above the clouds — truly unforgettable.
Reserve sunrise access in advance on recreation.gov.
Morning: Stop at Kula Bistro for breakfast on the way back.
Spend the rest of the day resting by the Ho’olei pool.
Dinner: Spago Maui for fine dining and a sunset view.
Day 6 – Sunset Sail
Main attraction: Early evening sail with Kai Kanani Sailing
Enjoy a 2 hour excursion departing from Maluaka Beach near Makena.
Lunch: Enjoy Loulu, located in the Grand Wailea Resort for sandwiches and locally brewed coffee.
Evening: Depending on the time of your sunset sail, either dine on the Kai Kanani sailboat or visit Fred’s Mexican Cafe in nearby Kihei.
Day 7 – Makena State Park
Main attraction: Makena State Park -Big Beach
Spend your final day soaking up Maui’s raw beauty at Big Beach, just south of Wailea.
Long, wide, and dramatic — perfect for photos and sunbathing (but watch for shore break).
Optional short hike over the lava hill to clothing optional Little Beach.
Lunch: Manoli’s Pizza in Wailea.
Evening: One last sunset from Wailea Beach Path before heading home.
