16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii journey builder

Plan created by another user. Make it yours

Route & dates

1
Honolulu, Oahu
— 3 nights
2
Waikoloa, Island of Hawaii
— 6 nights
3
Wailea, Maui
— 5 nights

3
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.
Honolulu is known for historic sites, wildlife, and beaches. Your plan includes some of its best attractions: go for a walk through Diamond Head State Monument, explore the activities along Hanauma Bay Nature Preserve, take in the dramatic scenery at Manoa Falls, and browse the exhibits of USS Arizona Memorial.

To find other places to visit, photos, more things to do, and tourist information, refer to the Honolulu trip planner.

Chicago to Honolulu is an approximately 12-hour flight. The time zone difference when traveling from Chicago to Honolulu is minus 4 hours. Traveling from Chicago in July, plan for somewhat warmer nights in Honolulu, with lows around °F. On the 25th (Thu), you'll travel to Waikoloa.

Things to do in Honolulu

Parks Outdoors Trails
Find places to stay Jul 22 — 25:
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
USS Arizona Memorial ©
USS Arizona Memorial

6
nights
Waikoloa, Island of Hawaii

Waikoloa ©
Waikoloa Village is a census-designated place (CDP) in Hawaii County, Hawaii, United States. Your day-by-day itinerary now includes Mauna Kea, Manta Ray Dives of Hawaii and Flumin’ Kohala. Venture out of the city with trips to Hilo (Rainbow Falls & Akaka Falls State Park). The adventure continues: admire the majestic nature at Hapuna Beach State Recreation Area, discover the deep blue sea with a scuba or snorkeling tour, identify plant and animal life at Waikoloa Petroglyph Preserve, and contemplate the long history of Puako Petroglyph Archaeological Preserve.

Before you visit Waikoloa, use our trip planner to discover what you can do and see there.

Getting from Honolulu to Waikoloa by flight takes about 4.5 hours. In July in Waikoloa, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 31st (Wed) early enough to travel to Wailea.

Things to do in Waikoloa

Outdoors Parks Wildlife

Side Trips

Kailua-Kona, Island of Hawaii, Hilo, Hapuna Beach State Recreation Area, Flumin’ Kohala
Find places to stay Jul 25 — 31:
Highlights from your plan
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Akaka Falls State Park ©
Akaka Falls State Park
Manta Ray Dives of Hawaii ©
Manta Ray Dives of Hawaii

5
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Your day-by-day itinerary now includes Molokini and Lanai Snorkeling Day Tour as well as Trilogy Excursions. You'll find plenty of places to visit near Wailea: Haleakala National Park (Pools at Ohe'o & Pipiwai Trail). Next up on the itinerary: kick back and relax at Wailea Beach, stroll through Keawakapu Beach, stop by Sweet Paradise Chocolatier, and contemplate the geological forces at Molokini Crater.

To see maps, photos, traveler tips, and more tourist information, go to the Wailea vacation tool.

Traveling by flight from Waikoloa to Wailea takes 4 hours. Alternatively, you can drive. In July, plan for daily highs up to °F, and evening lows to °F. On the 5th (Mon), you'll have the morning to explore before heading back home.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Maui, Haleakala National Park, Trilogy Excursions, Molokini and Lanai Snorkeling Day Tour
Find places to stay Jul 31 — Aug 5:
Highlights from your plan
Wailea Beach ©
Wailea Beach
Trilogy Excursions ©
Trilogy Excursions
Makena Beach ©
Makena Beach

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