20 days in Hawaii Itinerary

Created using Inspirock Hawaii tour planner
Make it your trip
Fly
1
Honolulu, Oahu
— 9 nights
Fly to Kona, Bus to Naalehu
2
Naalehu, Island of Hawaii
— 2 nights
+2
Drive to Ellison Onizuka Kona International Airport at Keahole, Fly to Kahului Airport, Drive to Haleakala National Park
3
Haleakala National Park, Maui
— 2 nights
Drive
4
Wailea, Maui
— 5 nights
Fly

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Honolulu, Oahu — 9 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Let the collections at Shangri La and Bishop Museum capture your imagination. You'll explore the less-touristy side of things at Koko Crater Railway Trail and Waimanalo Beach. Change things up with these side-trips from Honolulu: Haleiwa (Waimea Bay, Sunset Beach Park, &more), Byodo-In Temple (in Kaneohe) and Ko Olina Lagoons (in Ko Olina). There's lots more to do: enjoy the sand and surf at Kailua Beach Park, tour the pleasant surroundings at Turtle Bay Beach, stroll around Ala Moana Beach Park, and get to know the fascinating history of Makapuu Lighthouse Trail.

You can plan Honolulu trip in no time by asking Inspirock to help create your itinerary.

San Francisco to Honolulu is an approximately 7-hour flight. The time zone changes from Pacific Standard Time (PST) to Hawaii-Aleutian Standard Time (HST), which is usually a -2 hour difference. Expect a bit warmer temperatures when traveling from San Francisco in August; daily highs in Honolulu reach 88°F and lows reach 75°F. On the 5th (Mon), you're off to Naalehu.
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Side Trips
Find places to stay Aug 27 — Sep 5:

Naalehu, Island of Hawaii — 2 nights

Naalehu is a census-designated place in Hawaii County, Hawaii. Kick off your visit on the 5th (Mon): contemplate in the serene atmosphere at Wood Valley Temple. Here are some ideas for day two: explore the fascinating underground world of Kula Kai Caverns, relax in the rural setting at Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz, and then enjoy the sand and surf at Papakōlea Green Sand Beach.

To find ratings, maps, photos, and tourist information, read our Naalehu day trip planning website.

Do a combination of flight and bus from Honolulu to Naalehu in 5.5 hours. When traveling from Honolulu in September, plan for slightly colder days in Naalehu, with highs around 72°F, while nights are much colder with lows around 49°F. Wrap up your sightseeing on the 7th (Wed) to allow time to travel to Haleakala National Park.
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Find places to stay Sep 5 — 7:

Haleakala National Park, Maui — 2 nights

A Rare and Sacred Landscape

Haleakala National Park offers visitors the rare opportunity to walk down into the intact crater of a volcano.
On the 7th (Wed), relax in the rural setting at ONO Organic Farms, then don't miss a visit to Charles Lindbergh's Grave, then look for all kinds of wild species at Pools at Ohe'o, and finally explore by horseback at Pipiwai Trail. Keep things going the next day: take in the exciting artwork at Laura Mango, contemplate in the serene atmosphere at Kahanu Garden, then immerse yourself in nature at Wai'anapanapa State Park, and finally take in the exciting artwork at Hana Coast Gallery.

For ratings, more things to do, other places to visit, and more tourist information, refer to the Haleakala National Park holiday tool.

The Route module can help you plan travel from Naalehu to Haleakala National Park. Traveling from Naalehu in September, you will find days in Haleakala National Park are a bit warmer (90°F), and nights are much warmer (72°F). You'll have a few hours on the 9th (Fri) to wrap things up before traveling to Wailea.
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Find places to stay Sep 7 — 9:

Wailea, Maui — 5 nights

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. You'll explore and learn at Alexander & Baldwin Sugar Museum and Ocean Science Discovery Center. Do some cultural sightseeing at Saint Theresa Roman Catholic Church and Keawala'i Congregational Church. Explore Wailea's surroundings by going to Ho'okipa Beach Park (in Paia) and Kapalua (Kapalua Beach & D.T. Fleming Park). There's much more to do: enjoy the sand and surf at Ulua Beach, stroll through Little Beach, work some fitness into your day at Wailea Beach Path, and add some adventure to your tour with a kayaking and canoeing tour.

To find reviews and more tourist information, read our Wailea day trip tool.

Explore your travel options from Haleakala National Park to Wailea with the Route module. In September, daytime highs in Wailea are 90°F, while nighttime lows are 72°F. Finish your sightseeing early on the 14th (Wed) to allow enough time to fly back home.
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Find places to stay Sep 9 — 14:

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.
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