8 days in Island of Hawaii Itinerary

8 days in Island of Hawaii Itinerary

Created using Inspirock Island of Hawaii tour planner

Make it your trip
Fly
1
Hilo
— 2 nights
Drive
2
Kailua-Kona
— 5 nights
Fly

S M T W T F S
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Hilo

— 2 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Explore Hilo's surroundings by going to Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Devastation Trail & Kilauea Iki Trailhead). The adventure continues: immerse yourself in nature at Akaka Falls State Park, take an unforgettable tour with a helicopter tour, browse the fresh offerings at Hilo Farmers Market, and admire the natural beauty at Hawaii Tropical Botanical Garden.

To find other places to visit, where to stay, and tourist information, refer to the Hilo trip builder site.

Chicago to Hilo is an approximately 15-hour flight. Traveling from Chicago to Hilo, you'll gain 4 hours due to the time zone difference. Traveling from Chicago in May, expect Hilo to be a bit warmer, temps between 82°F and 67°F. Wrap up your sightseeing on the 10th (Mon) to allow time to drive to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Tours · Nature

Side Trips

Kailua-Kona

— 5 nights

Heart of the Kona Coast

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.
Get out of town with these interesting Kailua-Kona side-trips: Pu'uhonua O Honaunau National Historical Park (in Honaunau), Kealakekua Bay (in Captain Cook) and Hapuna Beach State Recreation Area (in Puako). The adventure continues: take your sightseeing to a higher altitude at Mauna Kea, take a stroll through Holualoa Village, take an in-depth tour of Kona Coffee Living History Farm, and sample the tasty concoctions at Ola Brew.

To find traveler tips, photos, reviews, and more tourist information, use the Kailua-Kona day trip website.

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. Plan for a bit warmer nights when traveling from Hilo in May since evenings lows in Kailua-Kona dip to 73°F. Wrap up your sightseeing on the 15th (Sat) early enough to travel back home.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Wildlife

Side Trips

Island of Hawaii travel guide

4.5
Swim with Dolphins · Scuba & Snorkeling · Beaches
The Big Island
Aptly nicknamed the "Big Island," the Island of Hawaii features sunny, black-sand beaches on the western side by Kona and a tropical rain forest on the eastern by Hilo. In between, the massive mountain Maunaloa covers half the island, and Kilauea, one of the world's most active volcanoes, erupts continuously. Twice as large as all the other Hawaiian Islands combined, this big chunk of land in the Pacific manages to retain a laid-back atmosphere despite its immense popularity with tourists. Instead of spending your entire vacation at one of the island's luxurious tourist resorts, go on tours of this Pacific haven's coffee and macadamia nut plantations and working ranches, or explore its nature reserves and rugged trails.