8 days in Hawaii Itinerary

8 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

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Route & dates

8 days in Hawaii Itinerary

Start: Chicago
Fly:  11​h 30​min
1
Honolulu, Oahu
— 2 nights
Fly:  4​h 15​min
2
Volcano, Island of Hawaii
— 2 nights
Fly:  3​h
3
Wailea, Maui
— 2 nights
Fly:  11​h 15​min
End: Chicago

2
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.
Kick off your visit on the 29th (Mon): go for a walk through Diamond Head State Monument. Here are some ideas for day two: examine the collection at Bishop Museum, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, and then surround yourself with nature on a nature and wildlife tour.

To find traveler tips, where to stay, more things to do, and tourist information, go to the Honolulu trip planner .

Chicago to Honolulu is an approximately 11.5-hour flight. The time zone difference when traveling from Chicago to Honolulu is minus 4 hours. Traveling from Chicago in July, expect somewhat warmer with lows of 75°F in Honolulu. Finish up your sightseeing early on the 31st (Wed) so you can travel to Volcano.

Things to do in Honolulu

Outdoors Parks Beaches
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Nature & Wildlife Tours

2
nights
Volcano, Island of Hawaii

Volcano ©
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Start off your visit on the 1st (Thu): take in the dramatic natural features at Thurston Lava Tube (Nahuku), then trek along Kilauea Iki Trailhead, then see the interesting displays at Jagger Museum, and finally immerse yourself in nature at Punalu‘U Beach. Get ready for a full day of sightseeing on the next day: get a taste of the local shopping with Volcano Garden Arts, get a taste of the local shopping with 2400 Fahrenheit Art Glass, then stop by Hilo Coffee Mill, then get a taste of the local shopping with Volcano Art Center, and finally contemplate the geological forces at Kīlauea.

To find where to stay, more things to do, and other tourist information, go to the Volcano trip itinerary planner .

Traveling by flight from Honolulu to Volcano takes 4.5 hours. In July, daily temperatures in Volcano can reach 85°F, while at night they dip to 71°F. Finish your sightseeing early on the 2nd (Fri) to allow enough time to travel to Wailea.

Things to do in Volcano

Parks Nature Museums

Side Trips

Hawaii Volcanoes National Park, Hilo Coffee Mill, Punalu‘U Beach
Highlights from your plan
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)
Punalu‘U Beach ©
Punalu‘U Beach
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead

2
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Kick off your visit on the 3rd (Sat): enjoy the sand and surf at Wailea Beach Path, tour the pleasant surroundings at Makena Beach, and then enjoy the sand and surf at Wailea Beach. Here are some ideas for day two: enjoy the sand and surf at Ulua Beach, enjoy the sand and surf at Keawakapu Beach, and then look for gifts at Sweet Paradise Chocolatier.

To see ratings, where to stay, maps, and other tourist information, go to the Wailea tour itinerary planning tool .

Getting from Volcano to Wailea by flight takes about 3 hours. In August in Wailea, expect temperatures between 90°F during the day and 73°F at night. Finish up your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Wailea

Outdoors Beaches Parks
Highlights from your plan
Wailea Beach ©
Wailea Beach
Ulua Beach ©
Ulua Beach
Wailea Beach Path ©
Wailea Beach Path

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