9 days in Hawaii Itinerary

9 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

This plan was created by another user. Make it your plan

Route & dates

Start: Chicago
Fly:  11 h 30 min
1
Honolulu, Oahu
— 3 nights
Fly:  3 h 45 min
2
Kailua-Kona, Island of Hawaii
— 2 nights
Fly + Bus:  4 h 45 min
3
Kihei, Maui
— 3 nights
Taxi + Fly:  11 h
End: Chicago

3
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Satisfy your inner culture vulture at USS Arizona Memorial and USS Bowfin Submarine Museum & Park. Take a break from the city and head to Diamond Head State Monument and Parasailing & Paragliding. Change things up with these side-trips from Honolulu: Haleiwa (Waimea Valley & Sunset Beach Park) and Sharks Cove (in Pupukea). There's more to do: get a dose of the wild on a nature and wildlife tour and enjoy the sand and surf at Kapiolani Regional Park.

To find traveler tips, reviews, and more tourist information, you can read our Honolulu attractions planner.

Chicago to Honolulu is an approximately 11.5- hour flight. Due to the time zone difference, you'll gain 4 hours traveling from Chicago to Honolulu. Traveling from Chicago in June, Honolulu is somewhat warmer at night with lows of 74°F. Wrap up your sightseeing on the 9th (Tue) to allow time to travel to Kailua-Kona.

Things to do in Honolulu

Outdoors Parks Tours

Side Trips

Haleiwa, Sharks Cove
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
USS Arizona Memorial ©
USS Arizona Memorial
Sunset Beach Park ©
Sunset Beach Park

2
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Start off your visit on the 10th (Wed): stop by Mountain Thunder Coffee Plantation, then enjoy the sand and surf at Manini'owali Beach (Kua Bay), then look for all kinds of wild species at Kanaloa Octopus Farm, and finally see what you can catch with a fishing tour. On the next day, take an in-depth tour of Kona Coffee Living History Farm, then contemplate the long history of Pu'uhonua O Honaunau National Historical Park, then enjoy the sand and surf at Honaunau Bay, and finally surround yourself with nature on a nature and wildlife tour.

To find other places to visit, ratings, and tourist information, read our Kailua-Kona trip planning site.

You can fly from Honolulu to Kailua-Kona in 4 hours. In June, daytime highs in Kailua-Kona are 85°F, while nighttime lows are 74°F. Finish your sightseeing early on the 11th (Thu) to allow enough time to travel to Kihei.

Things to do in Kailua-Kona

Outdoors Parks Wildlife

Side Trips

Honaunau, Kona Coffee Living History Farm
Highlights from your plan
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Pu'uhonua O Honaunau National Historical Park ©
Pu'uhonua O Honaunau National Historical Park
Honaunau Bay ©
Honaunau Bay

3
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Kick off your visit on the 12th (Fri): enjoy the sand and surf at Ulua Beach, kick back and relax at Makena Beach, and then tour the pleasant surroundings at Wailea Beach. Get ready for a full day of sightseeing on the next day: kick back and relax at Kamaole Beach Park II, kick back and relax at Kamaole Beach Park III, then look for gifts at Tutu's Pantry, and finally get interesting insight from Tours.

To find more things to do, where to stay, reviews, and tourist information, read our Kihei day trip planner.

You can do a combination of flight and bus from Kailua-Kona to Kihei in 5 hours. Other options are to do a combination of flight and bus; or do a combination of flight and car. In June, daytime highs in Kihei are 87°F, while nighttime lows are 71°F. Finish up your sightseeing early on the 14th (Sun) so you can travel back home.

Things to do in Kihei

Outdoors Beaches Parks

Side Trips

Wailea, Zipline
Highlights from your plan
Ulua Beach ©
Ulua Beach
Kamaole Beach Park II ©
Kamaole Beach Park II
Wailea Beach ©
Wailea Beach

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