Search Tours

Gallery Image
1 / 19

Super Hawaii: Maui and Kauai Hiking Tour

This two-in-one tour starts on the Valley Isle of Maui and continues to the Garden Isle of Kauai. Beaches, volcanoes, jungle, snorkeling – so much to explore.

Average Climate

No upcoming dates are currently available for this trip.

legend

Double Booking TBD

Single Booking TBD

Roommate Rebate TBD

Trip Type

Hiking

Difficulty Level

3

Trip Length

10 Days, 9 Nights

Distance

63 Miles
101.4 Kilometers

Meeting Time

8:30am hotel

Drop-off Time

5pm

Assembly Point

Kahului, HI

Inclusions

Intra island and Inter Island transportation is included. Not Included: Airline Service to Kahului Airport and departure from Lihui Airport; Guide Gratuity.

Lodging Highlights

  • Hana Kai Maui – Premium option
  • Waimea Plantation Cottages – Premium option
  • Hanalei Colony Inn – Premium option
  • The Hana Inn – Basic option
  • The West Inn – Basic option

Have questions? We’re here to help! Call us at 303-664-8388 or reach out online.

Contact For Details

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.

ITINERARY

Day 1: Meet in Kahului, drive the Hana Highway, hike the ancient Kings Highway

+

Distance: 5 miles

We’ll begin our tour on Day 1 in the gateway city of Kahului on Maui and start right off by driving the famous Hana Highway along the coastline. The higway is an indespensible ingredient in every Maui adventure, covering 50 miles, over 600 switchbacks, and 50 bridges. We stop along the way to trace a portion of the ancient Kings Highway from Pailoa Bay in Waianapanapa State Park to Kainalimu Bay. This coastal trail traverses wind swept cliffs overlooking blowholes, sea arches and tidal pools to an ancent Hawaiin Temple site. We continue to beautiful Hana, where we’ll spend our first two overnights.

Day 2: Hike the Pipiwai Trail to Waimoku Falls

+

Distance: 8 miles

Day 2 we continue a little farther west to the Pipiwai Trail and an arm of the Haleakalā National Park. After a stop at the visitor center, we’ll climb through open grasslands and bamboo forests past stunning Makahiku Falls to Waimoku Falls, our turn-around point. Our return to Hana should be early enough to explore this fascinating village.

Day 3: Transfer to the north side, hike onto Waihee Ridge, to Kehei for the night

+

Distance: 6.5 miles

Day 3 we’re off to the north on the flanks of Puʻu Kukui to hike Waihee Ridge and the rain forest of Kanoa Ridge overlooking Waihee Canyon. There are spectacular views in every direction, of lush rainforest valley, Makamakaole Falls in the distance, and many views of the ocean, isthmus and Haleakala side of Maui. This evening we head to Kihei and the beach for our next two nights.

Day 4: Hike into and across the Haleakala Crater

+

Distance: 12 miles

Day 4 is devoted to Haleakalia for what is consiered to be Maui’s signature hike. We’ll hike from the Visitors Center at Haleakala’s summit and descend into the volcano’s crater along the Sliding Sand Trail to the Holua Cabin, across the vallley floor, only to climb 1,500″ on the Hulemauu Trail to exit the crater.

Day 5: Early morning kayak and snorkel in Turtle Town, then inter island flight to Kauai, transfer to the north shore

+

We have a relaxing morning on Day 5 as we enjoy the beach and snorkle among the turtles in the bay. After lunch we head back to the airport in Kahului to catch the short flight to Kauai. We immediately head to Princeville township, a north shore community that started off as a sugar plantation. Our resort is nestled high into the cliff terrain of the area, offering views of both the inland mountains and the Pacific to the north.

Day 6: Kalalau Trail to Hanakapaia Beach and Hanakapaia Falls

+

Distance: 9.5 miles

The magnificent Kalalau Trail is our destination on Day 6. The trail leads from Ke’e Beach to Kalalau Beach along the famed Nāpali Coast. Originally built in the late 1800s, the trail serves as one of the only ways to access the beautiful Napali Coast via land. It crosses above towering sea cliffs and through lush tropical valleys then drops to sea level at Hanakapi’ai beach. We return to Princeville for the evening.

Day 7: Hike the Kuilau Ridge Trail and transfer to the south side.

+

Distance: 5 miles

Day 7, we make our way back around to the east side of the island for an exploration of the Kuilau Ridge, hiding behind the Sleeping Giant. The variety of plant life deep in the forest is astounding, and the trail leads you to amazing panoramas of Makaleha Mountains. After our hike, we continue around the island to the south side for our final three nights.

Day 8: Nualolo-Awaawapui Trail

+

Distance: 7 miles

Day 8 is a spectacular hike to the cliff’s edge on the southern NaPali Coast. From the ridge that forms Koke’e State Park, we take the Awa’awapuhi Trail west to the edge of the world. The incredibly steep ribs that fan out to the ocean look like flying buttresses, and in the deep blue waters below you can spot sail boats and sometimes whales.

Day 9: Kukui Trail into the Grand Canyon of the Pacific

+

Distance: 6 miles

Impressive Waimea Canyon, dubbed the Grand Canyon of the Pacific, is our plan for Day 9, along the Kukui Trail. The route drops 2,000 feet to the canyon floor for a lunch spot like no other. The hike back up gives us a new perspective on the unique flora of the area.

Day 10: Hike on Shipwreck Beach to Makauwahi Cave, back to Lihue Airport

+

Distance: 4 miles

Our last Day 10 of the tour brings us to Poipu Beach, where we’ll walk the coastline of Poipu along the Shiprock Beach Trail and climb a promontory for an incredible panoramic view of the cinder cones and lava tubes that extend into the ocean as evidence of Kauai’s most recent volcanic activity. Late that afternoon, we return to Lihue for the conclusion of our Super Hawaii Tour.

No related trips found.

Download Your Trip Itinerary

Fill out the form below to receive your complete itinerary, including daily schedules, accommodations, and more.