8 days in Island of Hawaii Itinerary

8 days in Island of Hawaii Itinerary

Created using Inspirock Island of Hawaii journey 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 the numerous day-trip ideas around Hilo: Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Devastation Trail & Kilauea Iki Trailhead). And it doesn't end there: admire the majestic nature at Akaka Falls State Park, browse the fresh offerings at Hilo Farmers Market, see the world from above with a helicopter tour, and get interesting insight from The Umauma Experience.

For more things to do, traveler tips, where to stay, and other tourist information, go to the Hilo route planner.

Chicago to Hilo is an approximately 15-hour flight. The time zone difference when traveling from Chicago to Hilo is minus 4 hours. While traveling from Chicago, expect somewhat warmer days and warmer nights in Hilo, ranging from highs of 84°F to lows of 70°F. Wrap up your sightseeing on the 29th (Thu) 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.
Explore the numerous day-trip ideas around Kailua-Kona: 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: fulfill a lifelong dream with a swim-with-the-dolphins experience, trek along Maka’ula ‘O’oma Tract, experience rural life at The Vanillerie, and stop by Holualoa Village.

For reviews, more things to do, and tourist information, you can read our Kailua-Kona trip planner.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In October, daytime highs in Kailua-Kona are 86°F, while nighttime lows are 75°F. Cap off your sightseeing on the 3rd (Tue) 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.