Experience the best of Maui with this itinerary, which covers everything from walking the Koloiki Ridge Trail to catching the sunrise from Wai‘anapanapa State Park to snorkeling at world-famous Ka‘anapali Beach.
Given Hawaii’s time zone, you may wake up before dawn. Take advantage by catching sunrise at Haleakala. Allow two hours of travel from Ka‘anapali or Wailea and plan to arrive 30 minutes before sunrise. Spend an hour hiking into the crater. On your way down, have breakfast at Kula Lodge or La Provence. Spend the rest of the day relaxing poolside. Conversely, spend the day relaxing at poolside, and catch sunset at Haleakala, for a less crowded and similarly beautiful experience, possibly lingering for stargazing.
Tackle another early-morning activity such as a snorkeling tour. Molokini tours depart from Ma‘alaea Harbor, while boats leave Ka‘anapali Beach for Olowalu or Honolua Bay. Finish by 2pm and spend the afternoon relaxing on the beach.
Enjoy Lahaina, ancient capital of the Hawaiian kingdom. Schedule a surf lesson or explore the town’s historic sites. Grab lunch at Aloha Mixed Plate or Cool Cat Café. Then head north to world-famous Ka‘anapali Beach, where you can snorkel, cliff jump, play in the surf, or rent a cabana. Explore the shops in Whalers Village, dine at Hula Grill.
Catch the 6:45am ferry to the island of Lana‘i. Book a Jeep ahead of time and spend the morning exploring. Pick a remote beach such as Polihua, Lopa, or Kaiolohia (Shipwreck Beach). Then head back to Lana‘i City for a plate lunch at Blue Ginger.
If you’d rather be hiking, call Rabaca’s for a taxi up into town and the trailhead for the Koloiki Ridge Trail. Explore Lana‘i City before catching a taxi down to Hulopo‘e Beach. Then make the short walk to Hulopo‘e Beach. Snorkel along the reef or relax in the shade with a book. Hike around the corner to the Pu‘u Pehe Overlook, keeping an eye out for the spinner dolphins. Rinse off at the beach shower, grab a drink at the Four Seasons Resort, and get back to the harbor to catch the 6:45pm ferry back to Maui.
Sleep in before grabbing a late breakfast. Those staying in West Maui should dine at The Gazebo, followed by a stroll along the Kapalua Coastal Trail. Drive to Kahakuloa, stopping on the way at the Nakalele Blowhole or the beach at Mokulei‘a Bay. If the conditions are calm and you can’t get enough snorkeling, head to Honolua Bay. End the day with happy hour at The Sea House restaurant.
If you’re staying in South Maui, brunch at Kihei Caffe before making the drive to Makena. Spend the day at Maluaka Beach, exploring to the end of the road, and walking the length of Big Beach just before sunset.
Drive to Pa‘ia and begin the day with a stroll down Baldwin Beach, followed by breakfast at Café des Amis. Enjoy the Road to Hana at a leisurely pace, taking time to hike to Twin Falls and explore the Ke‘anae Peninsula. Check into your accommodations in Hana and enjoy sunset from Hamoa Beach.
Catch the sunrise from Wai‘anapanapa State Park. Visit the popular Pools of ‘Ohe‘o before day-trippers arrive around 11am. Spend a couple of hours exploring the pools and hiking the Pipiwai Trail. If the weather is nice, wrap around the back side of the island on the narrow and rugged “back road.” Hike to Alelele Falls, grab a cold drink at the Kaupo Store, and experience a coast that feels like the end of the earth.
Downtime: Sleep in as late as you’d like, lounge by the pool, get a massage. Breathe deeply.
Spend the day in rural Upcountry. Enjoy breakfast on the lanai at Grandma’s Coffee House, followed by a stroll down Thompson Road. Drive to Ulupalakua for a midday wine-tasting, and then double back the way you came to the town of Makawao for some shopping and lunch at Polli’s Mexican Restaurant. Spend the afternoon in chic Pa‘ia, although don’t linger too long: You need to make it to the Old Lahaina Luau by 5pm to celebrate your last night on the island.
Gradually make your way toward Kahului Airport. Stop in at the Maui Ocean Center for one last glimpse of marinelife. Continuing on to Wailuku, make the short drive into ‘Iao Valley to see the famous needle. At Kanaha Beach Park, watch the windsurfers. Think about how you’ll miss Maui—and plan your next visit.