8 days in Maui Itinerary
Created using Inspirock Maui tour itinerary builder
Start: Chicago
Fly
1
Lahaina
— 4 nights
Drive
2
Haleakala National Park
— 3 nights
Fly
End: Chicago
Thu, Aug 3 - Thu, Aug 10
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Lahaina — 4 nights

Crown Jewel of Maui
Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.Bring the kids along to Ka'anapali Beach and Scuba & Snorkeling. You'll find plenty of places to visit near Lahaina: Helicopter Tours (in Kahului), Wailuku (Maui Tropical Plantation & Iao Valley) and Wailea Beach (in Wailea). And it doesn't end there: walk around Lahaina Banyan Court, take a memorable tour with Tours, enjoy the sand and surf at Kapalua Beach, and stop by Vintage European Posters.
To find other places to visit, reviews, traveler tips, and other tourist information, read Lahaina sightseeing planner.
Chicago to Lahaina is an approximately 11-hour flight. You'll gain 4 hours traveling from Chicago to Lahaina due to the time zone difference. Traveling from Chicago in August, expect somewhat warmer with lows of 74°F in Lahaina. Finish up your sightseeing early on the 7th (Mon) so you can travel to Haleakala National Park.
Side Trips
Find places to stay Aug 3 — 7:
Highlights from your trip
Haleakala National Park — 3 nights

A Rare and Sacred Landscape
Haleakala National Park offers visitors the rare opportunity to walk down into the intact crater of a volcano.Start off your visit on the 8th (Tue): take your sightseeing to a higher altitude at Haleakala Crater, then take in the architecture and atmosphere at Huialoha Church, then ride a horse along Pipiwai Trail, and finally don't miss a visit to Charles Lindbergh's Grave. Get ready for a full day of sightseeing on the 9th (Wed): admire all the interesting features of Hana Highway - Road to Hana.
To find where to stay, more things to do, and more tourist information, refer to the Haleakala National Park trip builder.
Use the Route module to find suitable travel options from Lahaina to Haleakala National Park. In August, daytime highs in Haleakala National Park are 90°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 10th (Thu) to allow time to fly back home.
Side Trips
Find places to stay Aug 7 — 10:
Highlights from your trip
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Maui travel guide
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.