Super Hawaii: Maui and Kauai Hiking Tour


(Contact Us to Request Dates)

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Linked Tour

Bonus Tour

Double Booking


Single Booking


Roommate Rebate


Tour cost includes 9 nights lodging, all meals, transportation on tour, entrance fees, guides, maps and narratives. Bonus Activity: Kayaking and snorkeling in Turtle Town

Assembly Point

Kahului, HI

Intra island and Inter Island transportation is included.

Not Included: Airline Service to Kahului Airport and departure from Lihui Airport; Guide Gratuity.

Meeting Time

8:30am hotel

Drop-off Time


“The best way to really see Hawaii is to hike it.”  Maureen H.

Hawaiian Islands Group Hiking Tours

Since 2007 Timberline has been taking hikers to the Hawaiian islands.  We have explored rain forests, waterfalls, deep canyons, wilderness shorelines, crater rims, lava ridges, and of course, sandy beaches.  The islands are truly a hiker’s paradise, made ever more appealing as we leave the crowds on the beach to explore the wonders within.  This year we are combining two of our favorite islands into a SUPER Hawaii tour – Maui and Kauai.

Since accommodations can run quite pricey on the island, we are providing two options for this tour.  Basic accommodations are in basic private rooms or cottages, with two nights having a shared bath.  Premium accommodations provide an upgrade to resort rooms or larger cottages, some with private beaches.  **These two island tours can also be booked separately – call the office for more information**

Hike Through Maui and Kauai

We begin our tour in the gateway city of Kahului on Maui and start right off by driving the famous Hana Highway along the coastline.  We have two nights in Hana where our hikes include cliffs, beaches, high waterfalls and bamboo forests.  We return to the central part of the island where we can reach Haleakala National Park.  We’ll be hiking into the crater and climbing along lush ridges.  On our last morning on Maui we plan to kayak and snorkel in Turtle Town – a truly memorable event.  Then a quick 40 minute* island hopping flight will take us to the Garden Isle – Kauai.  Recovering from the devastating floods of 2018, the government has reopened an improved entry to the famed Napali Coast.  Our hike on the Kalalau trail along this coastline has to be a highlight of our Hawaii tour.  After two nights on the north side, we transfer to the south end of Kauai for its access to Waimea Canyon – the “Grand Canyon of the Pacific”.  Hiking both into the canyon, and out onto the ribs of cliffs that rise 4000 ft* from the Napali Coast will show us the ruggedness of the island that many visitors miss.  Our last day includes a hike on Shipwreck beach, a visit to Makauwahi Cave, and perhaps a last swim at Poipu beach, before returning to Lihui for the end of our Super Hawaii Hiking Tour.

*In Timberline’s 40th anniversary year, we are celebrating all things 40

See Detailed Itinerary Here:

Interested in other biking or hiking tours in the USA or Canada? Contact Timberline Adventures here to schedule your journey today!


Day 1Meet in Kahului, drive the Hana Highway, hike the ancient Kings Highway5
Day 2Hike the Pipiwai Trail to Waimoku Falls8
Day 3Transfer to the north side, hike onto Waihee Ridge, to Kehei for the night6.5
Day 4Hike into and across the Haleakala Crater12
Day 5Early morning kayak and snorkel in Turtle Town, then inter island flight to Kauai, transfer to the north shore
Day 6Kalalau Trail to Hanakapaia Beach and Hanakapaia Falls9.5
Day 7Hike the Kuilau Ridge Trail and transfer to the south side.5
Day 8Nualolo-Awaawapui Trail7
Day 9Kukui Trail into the Grand Canyon of the Pacific6
Day 10Hike on Shipwreck Beach to Makauwahi Cave, back to Lihue Airport4

Total Distance: 63 miles

Super Hawaii: Maui and Kauai Hiking Tour


(Contact Us to Request Dates)