17 days in Honolulu & Maui Itinerary

17 days in Honolulu & Maui Itinerary

Created using Inspirock Hawaii attractions planner

Make it your trip
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Honolulu
— 7 nights
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Lahaina
— 8 nights
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Honolulu

— 7 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Change things up with these side-trips from Honolulu: Haleiwa (Sunset Beach Park & Waimea Bay), Pupukea (Ehukai Beach Park & Pu’u O Mahuka Heiau State Monument) and Lanikai Beach (in Kailua). Next up on the itinerary: take in the pleasant sights at Diamond Head State Monument, admire the landmark architecture of Shangri La, take in the dramatic scenery at Manoa Falls, and enjoy the sand and surf at Waikiki Beach.

For other places to visit, where to stay, reviews, and other tourist information, refer to the Honolulu sightseeing planning app.

Chicago to Honolulu is an approximately 12-hour flight. You'll gain 4 hours traveling from Chicago to Honolulu due to the time zone difference. Traveling from Chicago in August, expect a bit warmer with lows of 75°F in Honolulu. Finish up your sightseeing early on the 3rd (Fri) so you can travel to Lahaina.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Lahaina

— 8 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.
Explore the numerous day-trip ideas around Lahaina: Helicopter Tours (in Kahului), Paia (Paia Peace Stupa & Ho'okipa Beach Park) and Wailea (Makena Beach, Wailea Beach, &more). There's still lots to do: discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Napili Beach, walk around Lahaina Banyan Court, and get up close and personal with brilliant marine life at Maui Ocean Center.

For where to stay, traveler tips, photos, and tourist information, read our Lahaina holiday maker.

Traveling by flight from Honolulu to Lahaina takes 4 hours. In September, daily temperatures in Lahaina can reach 86°F, while at night they dip to 74°F. Cap off your sightseeing on the 11th (Sat) early enough to travel back home.

Things to do in Lahaina

Parks · Outdoors · Beaches · Tours

Side Trips

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Luaus
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.