An island-hopping itinerary for Maui, Molokai and Hawaii Island

Visit a handful of islands with this custom adventure.
Hamoa Beach near the town on Hana on the east side of Maui, Hawaii

Start on Maui …

Start your island hopping on Maui for five days, and stay at the dreamy Paia Inn fronting a quiet, white-sand beach. Located centrally in the hip north shore town of Paia, there’s plenty of shopping, food and activities to keep you busy. It’s also a convenient starting point for two trips you’ll want to make on the east side of Maui. On day one, drive to the summit of Haleakala to watch the sunrise (get your permit in advance), then visit Maui Wine, Alii Kula Lavender Farm or Kula Lodge while you’re Upcountry. The next day, meet Blue Hawaiian Helicopters at Kahului Airport for a spectacular tour of the West Maui mountains and valleys with streaming waterfalls, before it takes you over the Pailolo Channel to see the world’s highest sea cliffs on the island of Molokai, and the Kalaupapa Peninsula. On days three through five, check out of your hotel and drive to the beautiful, remote town of Hana for two nights at the all-inclusive boutique hotel, Travaasa Hana, which you can use as a home base to hike the Pipiwai Trail at the Kipahulu District of Haleakala National Park, explore Hana Lava Tube, see Kahanu Garden and lounge on the black-sand beach at Waianapanapa State Park.


Fly to Molokai …

Anakala Pilipo Solaotorio at Halawa Valley, Molokai.
Photo: PF Bentley

Fly to the Friendly Isle of Molokai on Mokulele Airlines—an experience likened to a helicopter—and stay a couple of nights at the only hotel on the island, Hotel Molokai. Visit Kaunakakai Town, book the Halawa Valley Falls Cultural Hike with Native Hawaiians Anakala Pilipo Solatorio (the last living descendant to be born and raised in Halawa) and his son Gregory, who will lead you on foot to Mooula Falls and teach you traditional Hawaiian protocol, or spend the day at the island’s largest beach, Papohaku. On your second day, take a Kalaupapa Mule Tour down the 1,700-foot-high sea cliff to the Kalaupapa National Historical Park. You’ll learn about the history of Hansen’s disease patients in Hawaii, who were banished to this isolated peninsula, and of the selfless caregivers, Father Damien and Mother Marianne, who helped take care of the population. 


Finish on Hawaii Island

big island
Hawaii Island’s stunning Halemaumau Crater. 
Photo: Thinkstock

Book a flight from Molokai to Hilo, through Maui, and choose to stay at one of three jaw-dropping destinations: The Inn at Kulaniapia, where views of its own private 120-foot waterfall are matched by the ability of guests to swim and kayak at its base; Waipio Inn B&B, where you can wake up to the sight of Waipio Valley’s stunning black-sand beach from its rim and hike by foot to the valley floor in the day; or Volcano House, because waking up to views of Halemaumau’s Crater are unlike anything else in the world. If that’s not the ultimate dream in and of itself, also visit the beauty of Akaka Falls’ 422-foot-high drop, walk Hilo’s historic town, taste a unique pinot noir from Volcano Winery and spend an entire day at Hawaii Volcanoes National Park. Then end your island-hopping adventure by booking a tour to the summit of Mauna Kea to see the stars like you’ve never seen them before.

Categories: Hawai‘i Island, Maui, Molokaʻi