14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

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Route & dates

14 days in Hawaii Itinerary

Start: New York City
foot + Fly:  19​h
1
Poipu, Kauai
— 4 nights
Fly:  3​h
2
Honolulu, Oahu
— 4 nights
Fly:  3​h
3
Wailea, Maui
— 4 nights
Fly + bus:  14​h
End: New York City

4
nights
Poipu, Kauai

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 Hanalei Beach, Keoki's Paradise, Poipu Beach Park, and other attractions. Step out of the city life by going to Waimea Canyon State Park and Hanalei Valley Lookout. The adventure continues: enjoy the sand and surf at Shipwreck Beach and explore the striking landscape at Spouting Horn.

For reviews, ratings, maps, and other tourist information, read Poipu trip planner .

New York City to Poipu is an approximately 16-hour combination of flight and taxi. You can also do a combination of bus, flight, and taxi; or do a combination of train, flight, and taxi. The time zone changes from Eastern Standard Time (EST) to Hawaii Standard Time (HST), which is usually a -5 hour difference. In July in Poipu, expect temperatures between 84°F during the day and 74°F at night. Wrap up your sightseeing by early afternoon on the 21st (Sat) to allow time for travel to Honolulu.

Things to do in Poipu

Parks Outdoors Nature

Side Trips

Hanalei, Kauai, Wailua Falls, Na Pali Coast State Park, Waimea Canyon State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Poipu Beach Park ©
Poipu Beach Park

4
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.
Your day-by-day itinerary now includes Lanikai Beach as well as Makapuu Lighthouse Trail. You'll enjoy a bit of beach vacationing at Hanauma Bay Nature Preserve and Waikiki Beach. Iolani Palace and USS Bowfin Submarine Museum & Park will appeal to museum buffs. Step out of Honolulu to go to Kailua and see Kailua Beach Park, which is approximately 32 minutes away. There's still lots to do: steep yourself in history at USS Arizona Memorial and take in the pleasant sights at Diamond Head State Monument.

For traveler tips, more things to do, other places to visit, and more tourist information, read our Honolulu trip planning site .

You can do a combination of taxi and flight from Poipu to Honolulu in 3 hours. In July, daily temperatures in Honolulu can reach 88°F, while at night they dip to 75°F. Wrap up your sightseeing on the 25th (Wed) early enough to travel to Wailea.

Things to do in Honolulu

Parks Outdoors Historic Sites

Side Trip

Kailua
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

4
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 Crater, Old Lahaina Luau, Lahaina Front Street, and other attractions you added. Get in touch with nature at Haleakala Crater and Wailea Beach. Go for a jaunt from Wailea to Hana to see Hasegawa's General Store about 1h 30 min away.

Planning Wailea trip won't be overwheling when you use's Insprock itinerary maker.

You can do a combination of flight and taxi from Honolulu to Wailea in 3 hours. Alternatively, you can do a combination of flight and car. In July, daytime highs in Wailea are 89°F, while nighttime lows are 72°F. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow time for travel back home.

Things to do in Wailea

Parks Nature Outdoors

Side Trips

Lahaina, Hana, Molokini Crater, Haleakala Crater
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Ka'anapali Beach ©
Ka'anapali Beach
Wailea Beach ©
Wailea Beach

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