14 days in Kauai Itinerary

14 days in Kauai Itinerary

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Route & dates

14 days in Kauai Itinerary

Start: Chicago
Fly + Drive:  13​h 45​min
1
Wailua
— 5 nights
Drive:  45​min
2
Hanalei
— 7 nights
Fly:  14​h
End: Chicago

5
nights
Wailua

Wailua ©
Wailua is a census-designated place in Kauai County, Hawaii, United States. Discover out-of-the-way places like Opaekaa Falls and Wailua Beach. Step out of the city life by going to Fern Grotto and Wet and Dry Caves, Kauai. The adventure continues: stroll around Lydgate State Park, immerse yourself in nature at Wailua River State Park, contemplate the long history of Poli'ahu Heiau, and enjoy the sand and surf at Hanamaulu Beach.

To see ratings, traveler tips, maps, and other tourist information, go to the Wailua online tour itinerary planner .

Chicago to Wailua is an approximately 14-hour flight. Traveling from Chicago to Wailua, you'll gain 4 hours due to the time zone difference. Prepare for a bit warmer weather when traveling from Chicago in May: high temperatures in Wailua hover around 82°F and lows are around 71°F. You will leave for Hanalei on the 4th (Tue).

Things to do in Wailua

Parks Nature Outdoors

Side Trip

Kauai
Highlights from your plan
Secret Falls (Uluwehi Falls) ©
Secret Falls (Uluwehi Falls)
Wailua River State Park ©
Wailua River State Park
Keahua Arboretum ©
Keahua Arboretum

7
nights
Hanalei

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Visit Secret Beach and Puu Poa Beach for some beach relaxation. You'll explore the less-touristy side of things at Spas and Fishing Charters & Tours. Change things up with these side-trips from Hanalei: Waimea (Koke'e Mountains & Waimea Canyon State Park) and Kokee Natural History Museum (in Kekaha). There's much more to do: get great views at Hanalei Valley Lookout, look for all kinds of wild species at Hanalei National Wildlife Refuge, pause for some serene contemplation at Wai`oli Hui`ia Church, and trek along Kalalau Trail.

For traveler tips, ratings, other places to visit, and more tourist information, go to the Hanalei tour itinerary planner.

Getting from Wailua to Hanalei by car takes about an hour. In June, plan for daily highs up to 83°F, and evening lows to 73°F. On the 11th (Tue), you'll have the morning to explore before heading back home.

Things to do in Hanalei

Parks Outdoors Wildlife

Side Trips

Kauai, Waimea, Kekaha, Na Pali Coast State Park, Puu Poa Beach
Highlights from your plan
Koke`e State Park ©
Koke`e State Park
Secret Beach ©
Secret Beach
Na Pali Coast State Park ©
Na Pali Coast State Park

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