16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock United States route planner

Plan created by another user. Make it yours
1
Honolulu, Oahu
— 5 nights
2
Poipu
— 4 nights
3
Ka'anapali, Maui
— 5 nights

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Learn more about your trip

5
nights
Honolulu, Oahu

Honolulu ©

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day by day itinerary now includes Sunset Beach Park, Polynesian Cultural Center, Honolulu Zoo, and other attractions you added. Go for a jaunt from Honolulu to Kailua to see Kailua Beach Park about 32 minutes away. The adventure continues: take in the pleasant sights at Diamond Head State Monument.

For where to stay, maps, more things to do, and other tourist information, use the Honolulu trip website.

Chicago to Honolulu is an approximately 12-hour flight. You can also fly. You'll gain 4 hours traveling from Chicago to Honolulu due to the time zone difference. Expect somewhat warmer evenings in Honolulu when traveling from Chicago in August, with lows around 75°F. You'll have a few hours on the 6th (Fri) to wrap things up before traveling to Poipu.

Things to do in Honolulu

Outdoors · Parks · Beaches · Adventure

Side Trips

Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Kailua Beach Park ©
Kailua Beach Park
Sunset Beach Park ©
Sunset Beach Park

4
nights
Poipu

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Your list of things to see and do now includes Best of Kauai Tour, Kauai Hiking Tours, Kipu Ranch Adventures, and other attractions.

Make your Poipu itinerary with Inspirock to find out what to see and where to go.

Traveling by flight from Honolulu to Poipu takes 3 hours. In August, daytime highs in Poipu are 86°F, while nighttime lows are 76°F. On the 10th (Tue), you'll have the morning to explore before heading off to Ka'anapali.

Things to do in Poipu

Outdoors · Tours · Wildlife · Nightlife

Side Trips

Highlights from your plan
Kipu Ranch Adventures ©
Kipu Ranch Adventures
Kauai Backcountry Adventures ©
Kauai Backcountry Adventures
Kauai Hiking Tours ©
Kauai Hiking Tours

5
nights
Ka'anapali, Maui

Ka'anapali ©
Perched at the western tip of Maui, the tourist hub of Ka'anapali offers a range of resorts and activities revolving around the beach.
Your day by day itinerary now includes Hana Highway - Road to Hana, Whalers Village and Lahaina Front Street. Next up on the itinerary: whizz through the canopy at some of the top local zipline courses and adventure parks, get outside with Honokohau Bay, explore the striking landscape at Nakalele Blowhole, and look for all kinds of wild species at Honolua Bay.

To find out how to plan a trip to Ka'anapali, use our trip itinerary maker.

Traveling by flight from Poipu to Ka'anapali takes 6 hours. Expect a daytime high around 86°F in August, and nighttime lows around 74°F. Finish your sightseeing early on the 15th (Sun) so you can travel back home.

Things to do in Ka'anapali

Outdoors · Scenic Drive · Parks · Adventure

Side Trips

Highlights from your plan
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Lahaina Front Street ©
Lahaina Front Street
Honokohau Bay ©
Honokohau Bay

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