21 days in Maui, Molokai & Oahu Itinerary

21 days in Maui, Molokai & Oahu Itinerary

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21 days in Maui, Molokai & Oahu Itinerary

Jackson
taxi + Fly + taxi:  11​h 30​min
Kihei
— 6 nights
taxi + Fly + taxi:  1​h
Hana
— 3 nights
Travel:  4​h 45​min
Kalaupapa
— 2 nights
Fly:  4​h 45​min
Haleiwa
— 4 nights
Drive:  45​min
Honolulu
— 4 nights
Fly + taxi:  12​h 15​min
Jackson

6
days
Kihei

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Visit Ulua Beach and Kapalua Beach for some beach relaxation. Get in touch with nature at Kamaole Beach Park II and Kamaole Beach Park III. Explore Kihei's surroundings by going to Lahaina (Napili Beach & River Rafting & Tubing) and D.T. Fleming Beach Park (in Kapalua). Next up on the itinerary: kick back and relax at Ho'okipa Beach Park, tour the pleasant surroundings at Keawakapu Beach, stop by Sweet Paradise Chocolatier, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

To find traveler tips, reviews, ratings, and tourist information, read Kihei travel itinerary planner

Jackson to Kihei is an approximately 11.5-hour combination of taxi and flight. The time zone difference when traveling from Jackson to Kihei is minus 4 hours. Expect much warmer temperatures when traveling from Jackson in December; daily highs in Kihei reach 82°F and lows reach 66°F. Wrap up your sightseeing on the 27th (Wed) to allow time to travel to Hana.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Kapalua, Lahaina, Helicopter Tours, Ho'okipa Beach Park
Accommodations
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Ho'okipa Beach Park ©
Ho'okipa Beach Park
Wailea Beach ©
Wailea Beach
Napili Beach ©
Napili Beach

2
days
Hana

Hana ©
Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
Kick off your visit on the 28th (Thu): enjoy the sand and surf at Wai'anapanapa State Park and then pause for some photo ops at Fagan's Cross. On your second day here, explore the different monuments and memorials at Charles Lindbergh's Grave, identify plant and animal life at Pools at Ohe'o, and then ride a horse along Pipiwai Trail.

For reviews, traveler tips, maps, and other tourist information, read Hana trip itinerary planning app

You can do a combination of taxi and flight from Kihei to Hana in an hour. Another option is to drive. Traveling from Kihei in December, expect nights in Hana to be a bit warmer, around 74°F, while days are slightly colder, around 77°F. On the 30th (Sat), wrap the sightseeing up by early afternoon so you can travel to Kalaupapa.

Things to do in Hana

Parks Outdoors Beaches

Side Trips

Haleakala National Park, Charles Lindbergh's Grave
Accommodations
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Pipiwai Trail ©
Pipiwai Trail
Red Sand Beach (Kaihalulu Beach) ©
Red Sand Beach (Kaihalulu Beach)
Pools at Ohe'o ©
Pools at Ohe'o

1
day
Kalaupapa

Kalaupapa ©
Kalaupapa is a small unincorporated community on the island of Molokai in the U.S. Start off your visit on the 31st (Sun): stroll through Kapukahehu Beach and then kick back and relax at Kepuhi Beach.

To see where to stay and more tourist information, you can read our Kalaupapa trip planner

Use the Route module to find suitable travel options from Hana to Kalaupapa. Traveling from Hana in December, expect a bit cooler with lows of 66°F in Kalaupapa. Wrap up your sightseeing by early afternoon on the 1st (Mon) to allow time for travel to Haleiwa.

Things to do in Kalaupapa

Parks Outdoors Beaches

Side Trips

Molokai, Kepuhi Beach
Accommodations
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Kapukahehu Beach ©
Kapukahehu Beach

4
days
Haleiwa

Haleiwa ©
Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. Your itinerary includes some good beach time at Sunset Beach Park and Turtle Bay Beach. Get in touch with nature at Shark Diving and Sharks Cove. Step out of Haleiwa with an excursion to Kahuku Farms in Kahuku--about 34 minutes away. The adventure continues: kick back and relax at Waimea Bay, appreciate the views at Waimea Valley, stroll through Laniakea Beach, and don't miss a visit to North Shore.

For reviews, where to stay, other places to visit, and other tourist information, go to the Haleiwa day trip website

The Route module can help you plan travel from Kalaupapa to Haleiwa. In January, daytime highs in Haleiwa are 75°F, while nighttime lows are 62°F. Cap off your sightseeing on the 5th (Fri) early enough to go by car to Honolulu.

Things to do in Haleiwa

Outdoors Parks Beaches

Side Trips

Pupukea, Kahuku, North Shore
Accommodations
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Sunset Beach Park ©
Sunset Beach Park
Shark Diving
Waimea Bay ©
Waimea Bay

4
days
Honolulu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Take a break from the city and head to Swim with Dolphins and Lanikai Beach. You'll enjoy a bit of beach vacationing at Kailua Beach Park and Kapiolani Regional Park. Step out of Honolulu to go to Waianae and see Ka'ena Point State Park, which is approximately 1h 05 min away. There's lots more to do: appreciate the extensive heritage of Makapuu Lighthouse Trail, take an unforgettable tour with a helicopter tour, hike along Koko Crater Trail, and cruise along Makapu'u Point.

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Traveling by car from Haleiwa to Honolulu takes an hour. Alternatively, you can take a bus. In January in Honolulu, expect temperatures between 80°F during the day and 66°F at night. Wrap up your sightseeing on the 9th (Tue) early enough to travel back home.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Kailua, Waianae, Oahu, The Byodo-In Temple
Accommodations
Get expert advice on where to stay in Honolulu.
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Highlights from your plan
Lanikai Beach ©
Lanikai Beach
Kailua Beach Park ©
Kailua Beach Park
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail

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