7 days in Maui Itinerary

7 days in Maui Itinerary

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Route & dates

7 days in Maui Itinerary

Chicago
Fly + taxi:  11​h 15​min
Wailea
— 5 nights
taxi + Fly:  11​h 15​min
Chicago

5
days
Wailea

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Explore hidden gems such as Stand-Up Paddleboarding and Ulua Beach. Visiting Keawakapu Beach and Kapalua Beach will get you outdoors. Venture out of the city with trips to Lahaina (Kayaking & Canoeing & River Rafting & Tubing), Ho'okipa Beach Park (in Paia) and Zipline (in Haiku). There's lots more to do: identify plant and animal life at Honolua Bay, kick back and relax at Kamaole Beach Park II, get some jogging in at Wailea Beach Path, and stroll through Makena Beach.

To find other places to visit, reviews, traveler tips, and other tourist information, read Wailea day trip app .

Chicago to Wailea is an approximately 11.5-hour combination of flight and taxi. The time zone changes from Central Standard Time to Hawaii Standard Time, which is usually a -4 hour difference. Expect a bit warmer temperatures when traveling from Chicago in May; daily highs in Wailea reach 85°F and lows reach 68°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel back home.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Lahaina, Kihei, Zipline, Honolua Bay, Ho'okipa Beach Park
Accommodations
Get expert advice on where to stay in Wailea.
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Highlights from your plan
Ulua Beach ©
Ulua Beach
Stand-Up Paddleboarding
Honolua Bay ©
Honolua Bay

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