7 days in Maui Itinerary

7 days in Maui Itinerary

Created using Inspirock Maui trip itinerary maker

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Wailea
— 5 nights
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Wailea

— 5 nights
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Escape the urban bustle at Kapalua Beach and Zipline. Step off the beaten path and head to Keawakapu Beach and Wailea Beach Path. Venture out of the city with trips to Lahaina (Kayaking & Canoeing & River Rafting & Tubing) and Ho'okipa Beach Park (in Paia). There's more to do: kick back and relax at Kamaole Beach Park III and stroll through Kamaole Beach Park II.

For photos, ratings, traveler tips, and tourist information, go to the Wailea trip itinerary builder.

Chicago to Wailea is an approximately 11-hour flight. Traveling from Chicago to Wailea, you'll gain 4 hours due to the time zone difference. In May, Wailea is somewhat warmer than Chicago - with highs of 86°F and lows of 68°F. Wrap up your sightseeing on the 21st (Mon) early enough to fly back home.

Things to do in Wailea

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay May 16 — 21:

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Zipline
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.