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 Kamaole Beach Park II. Explore Wailea's surroundings by going to Ho'okipa Beach Park (in Paia), Lahaina (Kayaking & Canoeing & River Rafting & Tubing) and Zipline (in Haiku). The adventure continues: kick back and relax at Kamaole Beach Park III, stroll through Ulua Beach, and work some fitness into your day at Wailea Beach Path.

To find maps, photos, traveler tips, and more tourist information, read Wailea online trip planner.

Chicago to Wailea is an approximately 11-hour flight. You'll gain 4 hours traveling from Chicago to Wailea due to the time zone difference. Traveling from Chicago in May, expect Wailea to be somewhat warmer, temps between 86°F and 68°F. Wrap up your sightseeing on the 21st (Mon) to allow time to fly back home.
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.