11 days in Hawaii Itinerary

11 days in Hawaii Itinerary

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Route & dates

11 days in Hawaii Itinerary

Start: Chicago
Fly:  11​h 30​min
1
Honolulu, Oahu
— 2 nights
Fly + taxi:  3​h
2
Hanalei, Kauai
— 3 nights
Fly:  5​h
3
Volcano, Island of Hawaii
— 1 night
Fly + bus:  3​h
4
Wailea, Maui
— 3 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 11th (Thu): hike along Diamond Head State Monument. Get ready for a full day of sightseeing on the next day: admire the verdant scenery at Nuuanu Pali Lookout, stroll through Lanikai Beach, then take in the spiritual surroundings of Byodo-In Temple, and finally stroll the grounds of USS Arizona Memorial.

To find ratings, more things to do, other places to visit, and tourist information, use the Honolulu trip itinerary 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. Expect warmer temperatures when traveling from Chicago in April; daily highs in Honolulu reach 83°F and lows reach 71°F. Finish up your sightseeing early on the 13th (Sat) so you can travel to Hanalei.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Lanikai Beach, Byodo-In Temple, Nu’uanu Pali
Highlights from your plan
Lanikai Beach ©
Lanikai Beach
Waikiki Beach ©
Waikiki Beach
USS Arizona Memorial ©
USS Arizona Memorial

3
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Take a break from the city and head to Kilauea Point National Wildlife Refuge and Kalalau Trail. Eschew the tourist crowds and head to Hanalei Beach and Dolphin & Whale Watching. There's lots more to do: admire the majestic nature at Na Pali Coast State Park, pause for some serene contemplation at Wai`oli Hui`ia Church, enjoy the sand and surf at Tunnels Beach, and get great views at Hanalei Valley Lookout.

For reviews, traveler tips, more things to do, and tourist information, read our Hanalei trip builder website .

Traveling by combination of flight and taxi from Honolulu to Hanalei takes 3 hours. April in Hanalei sees daily highs of 80°F and lows of 70°F at night. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel to Volcano.

Things to do in Hanalei

Parks Wildlife Outdoors

Side Trips

Kauai, Queen's Bath, Kilauea Point National Wildlife Refuge, Na Pali Coast State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Hanalei Beach ©
Hanalei Beach
Kilauea Point National Wildlife Refuge ©

1
night
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.
Kick off your visit on the 17th (Wed): shop like a local with Volcano Garden Arts, explore the striking landscape at Thurston Lava Tube (Nahuku), then tour the pleasant surroundings at Kilauea Iki Trailhead, then take in the exciting artwork at Volcano Art Center, and finally examine the collection at Jagger Museum.

To see maps, more things to do, other places to visit, and tourist information, read Volcano holiday planner.

Traveling by flight from Hanalei to Volcano takes 5 hours. Alternatively, you can do a combination of flight and bus. In April, daily temperatures in Volcano can reach 81°F, while at night they dip to 67°F. Finish your sightseeing early on the 17th (Wed) so you can travel to Wailea.

Things to do in Volcano

Parks Museums Shopping

Side Trip

Hawaii Volcanoes National Park
Highlights from your plan
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Jagger Museum ©
Jagger Museum

3
nights
Wailea, Maui

Wailea
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. We've included these beaches for you: Wailea Beach Path and Makena Beach. Get outdoors at Ulua Beach and Keawakapu Beach. Get out of town with these interesting Wailea side-trips: Pipiwai Trail (in Haleakala National Park), Charles Lindbergh's Grave (in Kipahulu) and Red Sand Beach (Kaihalulu Beach) (in Hana). There's more to do: enjoy the sand and surf at Wailea Beach and tour the pleasant surroundings at Pa'ako Beach (Secret Cove).

For traveler tips, ratings, maps, and more tourist information, refer to the Wailea road trip website .

You can fly from Volcano to Wailea in 3 hours. In April, plan for daily highs up to 85°F, and evening lows to 68°F. Wrap up your sightseeing on the 20th (Sat) early enough to travel back home.

Things to do in Wailea

Parks Outdoors Beaches

Side Trips

Red Sand Beach (Kaihalulu Beach), Charles Lindbergh's Grave, Pipiwai Trail
Highlights from your plan
Red Sand Beach (Kaihalulu Beach)
Red Sand Beach (Kaihalulu Beach)
Keawakapu Beach ©
Keawakapu Beach
Wailea Beach Path ©
Wailea Beach Path

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