18 days in Oahu, Maui & Kauai Itinerary

18 days in Oahu, Maui & Kauai Itinerary

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Route & dates

18 days in Oahu, Maui & Kauai Itinerary

Start: New York City
Bus + Fly:  9​h 30​min
1
Honolulu
— 3 nights
Fly + Drive:  4​h
2
Kipahulu
— 3 nights
Drive:  2​h 30​min
3
Lahaina
— 4 nights
Bus + Fly:  4​h 30​min
4
Waimea
— 2 nights
Drive:  1​h 30​min
5
Princeville
— 4 nights
Fly:  16​h 30​min
End: New York City

3
nights
Honolulu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get outdoors at Waikiki Beach and Kailua Beach Park. We've included these beaches for you: Sunset Beach Park and Kapiolani Regional Park. Go for a jaunt from Honolulu to Haleiwa to see Waimea Bay about 54 minutes away. And it doesn't end there: stroll through Diamond Head State Monument, contemplate the waterfront views at Hanauma Bay Nature Preserve, and admire the sheer force of Manoa Falls.

To see traveler tips, other places to visit, and tourist information, go to the Honolulu tour itinerary planning site .

New York City to Honolulu is an approximately 14-hour combination of bus and flight. You can also fly. The time zone difference moving from Eastern Standard Time to Hawaii Standard Time is minus 5 hours. Plan for somewhat warmer temperatures traveling from New York City in September, with highs in Honolulu at 36°C and lows at 28°C. Wrap up your sightseeing by early afternoon on the 12th (Wed) to allow enough time to travel to Kipahulu.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Kailua Beach Park
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Kailua Beach Park ©
Kailua Beach Park

3
nights
Kipahulu

Kipahulu ©
On the 13th (Thu), explore the striking landscape at Haleakala Crater, then take a memorable drive along Haleakala Highway (Crater Road), and then tour the pleasant surroundings at Pipiwai Trail. Here are some ideas for day two: immerse yourself in nature at Wai'anapanapa State Park.

Plan a trip to Kipahulu easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by combination of flight and car from Honolulu to Kipahulu takes 4 hours. Alternatively, you can do a combination of flight and taxi. September in Kipahulu sees daily highs of 38°C and lows of 26°C at night. You will leave for Lahaina on the 15th (Sat).

Things to do in Kipahulu

Parks Outdoors Nature

Side Trips

Haleakala National Park, Haleakala Highway (Crater Road), Wai'anapanapa State Park
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Wai'anapanapa State Park ©
Wai'anapanapa State Park
Haleakala Highway (Crater Road) ©
Haleakala Highway (Crater Road)

4
nights
Lahaina

Lahaina ©
Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
You'll get in some beach time at Ka'anapali Beach and Napili Beach. Escape the urban bustle at Wailea Beach and Iao Valley. Explore the numerous day-trip ideas around Lahaina: Dolphin & Whale Watching (in Kihei) and Maluaka Beach (in Wailea). There's much more to do: enjoy the sand and surf at Kapalua Beach, don't miss a visit to Lahaina Banyan Court, and admire nature's wide array of creatures at Maui Ocean Center.

For other places to visit, traveler tips, reviews, and more tourist information, read our Lahaina day trip planner .

Explore your travel options from Kipahulu to Lahaina with the Route module. Expect a daytime high around 35°C in September, and nighttime lows around 27°C. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel to Waimea.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailuku, Wailea, Kapalua Beach
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Wailea Beach ©
Wailea Beach
Kapalua Beach ©
Kapalua Beach

2
nights
Waimea

Waimea ©
Kick off your visit on the 20th (Thu): appreciate the extensive heritage of Kalalau Lookout, admire the majestic nature at Na Pali Coast State Park, and then take in breathtaking views at Waimea Canyon State Park. On the 21st (Fri), you'll have a packed day of sightseeing: tour the pleasant surroundings at Kalapaki Beach, take an unforgettable tour with a helicopter tour, and then kick back and relax at Poipu Beach Park.

Plan trip to Waimea with our itinerary maker to find out where to go and what to do.

Traveling by combination of bus, flight, and taxi from Lahaina to Waimea takes 4.5 hours. Expect a daytime high around 35°C in September, and nighttime lows around 27°C. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Princeville.

Things to do in Waimea

Parks Nature Outdoors

Side Trips

Lihue, Na Pali Coast State Park, Poipu Beach Park, Kalalau Lookout
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
Princeville

Princeville ©
Princeville is a 9,000acre, upscale, unincorporated, master-planned community of vacation homes and condos on the north shore of the island of Kauai in Kauai County, Hawaii. Step out of the city life by going to Hanalei Beach and Lumahai Beach. You'll get in some beach time at Tunnels Beach and Anini Beach. Next up on the itinerary: enjoy the sand and surf at Hanalei Bay, explore the striking landscape at Queen's Bath, take in the architecture and atmosphere at Wai`oli Hui`ia Church, and tour the pleasant surroundings at Ke'e Beach.

To find photos, traveler tips, more things to do, and other tourist information, you can read our Princeville attractions planning website .

You can drive from Waimea to Princeville in 1.5 hours. In September in Princeville, expect temperatures between 35°C during the day and 28°C at night. Wrap up your sightseeing on the 25th (Tue) early enough to travel back home.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Kauai, Hanalei, Ke'e Beach, Kilauea Point National Wildlife Refuge
Highlights from your plan
Hanalei Beach ©
Hanalei Beach
Tunnels Beach ©
Tunnels Beach
Anini Beach ©
Anini Beach

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