7 days in Maui Itinerary

7 days in Maui Itinerary

Created using Inspirock Maui trip itinerary maker

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Route & dates

Start: Chicago
Fly:  11 h 15 min
1
Wailea
— 5 nights
Fly:  11 h 15 min
End: Chicago

5
nights
Wailea

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Escape the urban bustle at Kapalua Beach and Ho'okipa Beach Park. Explore Wailea's surroundings by going to Zipline (in Haiku) and Lahaina (Kayaking & Canoeing & River Rafting & Tubing). The adventure continues: look for all kinds of wild species at Honolua Bay, kick back and relax at Kamaole Beach Park III, tour the pleasant surroundings at Ulua Beach, and get some jogging in at Wailea Beach Path.

To find other places to visit, where to stay, ratings, and other tourist information, read our Wailea trip itinerary planner.

Chicago to Wailea is an approximately 11.5-hour flight. 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 86°F and lows reach 68°F. Wrap up your sightseeing on the 21st (Mon) to allow time to travel back home.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Kihei, Lahaina, Zipline, Ho'okipa Beach Park, Kapalua Beach
Find places to stay May 16 — 21:
Highlights from your plan
River Rafting & Tubing
Zipline
Kapalua Beach ©
Kapalua Beach

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