12 days in Maui Itinerary

12 days in Maui Itinerary

Created using Inspirock Maui visit planner

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Route & dates

12 days in Maui Itinerary

Start: Chicago
Fly + Drive:  12​h 45​min
1
Hana
— 3 nights
Drive:  2​h 15​min
2
Kihei
— 8 nights
Fly:  11​h
End: Chicago

3
nights
Hana

Hana ©
Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
Museum-lovers will appreciate Hana Coast Gallery and Hana Cultural Center. Get in touch with nature at Wai'anapanapa State Park and Haleakala Crater. There's much more to do: take a memorable drive along Hana Highway - Road to Hana, take in the dramatic natural features at Ke‘anae Point, and kick back and relax at Hamoa Beach.

For other places to visit, traveler tips, reviews, and tourist information, refer to the Hana road trip planner .

Chicago to Hana is an approximately 13-hour combination of flight and car. You can also fly; or do a combination of subway, bus, flight, and car. The time zone changes from Central Standard Time (CST) to Hawaii Standard Time (HST), which is usually a -4 hour difference. Plan for warmer temperatures traveling from Chicago in November, with highs in Hana at 84°F and lows at 68°F. Wrap up your sightseeing on the 30th (Sat) early enough to drive to Kihei.

Things to do in Hana

Outdoors Parks Nature

Side Trips

Maui, Haleakala Crater
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Hamoa Beach ©
Hamoa Beach

8
nights
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.
Visiting Ka'anapali Beach and Stand-Up Paddleboarding will get you outdoors. Your itinerary includes some good beach time at Wailea Beach and Kamaole Beach Park III. Venture out of the city with trips to Kapalua (D.T. Fleming Beach Park & Kapalua Beach), Lahaina (Zipline, Baldwin Home Museum, & more) and Maui Hands (in Ka'anapali). And it doesn't end there: examine the collection at Hale Ho'ike'ike at the Bailey House, kick back and relax at Makena Beach, admire the majestic nature at Iao Valley, and tour the pleasant surroundings at Maluaka Beach.

To find traveler tips, reviews, maps, and more tourist information, read our Kihei trip maker .

You can drive from Hana to Kihei in 2.5 hours. Another option is to do a combination of flight and bus. In November, plan for daily highs up to 84°F, and evening lows to 68°F. Cap off your sightseeing on the 8th (Sun) early enough to travel back home.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Lahaina, Wailuku, Kapalua, Maui Hands
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Wailea Beach ©
Wailea Beach
Napili Beach ©
Napili Beach

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