14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary maker

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Route & dates

14 days in Hawaii Itinerary

Start: Auckland
Fly:  12​h 15​min
1
Poipu, Kauai
— 2 nights
Fly + bus:  3​h 15​min
2
Haleiwa, Oahu
— 3 nights
bus + Fly:  4​h 30​min
3
Kailua-Kona, Island of Hawaii
— 5 nights
Fly + bus:  4​h 45​min
4
Kihei, Maui
— 3 nights
Fly:  13​h 30​min
End: Auckland

2
nights
Poipu, Kauai

Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Start off your visit on the 5th (Thu): see some colorful creatures with a scuba or snorkeling tour and then enjoy the sand and surf at Polihale State Park. Here are some ideas for day two: take in the dramatic scenery at Opaekaa Falls, stroll through Tunnels Beach, and then kick back and relax at Shipwreck Beach.

For ratings, where to stay, photos, and more tourist information, use the Poipu sightseeing planner .

Auckland, New Zealand to Poipu is an approximately 12.5-hour flight. The time zone difference moving from New Zealand Standard Time (NZST) to Hawaii Standard Time (HST) is minus 22 hours. Prepare for much hotter weather when traveling from Auckland in September: high temperatures in Poipu hover around 35°C and lows are around 28°C. Cap off your sightseeing on the 6th (Fri) early enough to travel to Haleiwa.

Things to do in Poipu

Outdoors Parks Beaches

Side Trips

Kauai, Scuba & Snorkeling, Polihale State Park
Find places to stay Sep 4 — 6:
Highlights from your plan
Scuba & Snorkeling
Polihale State Park ©
Polihale State Park
Shipwreck Beach ©
Shipwreck Beach

3
nights
Haleiwa, Oahu

Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. You'll discover tucked-away gems like Ko Olina Lagoons and Turtle Bay Beach. Get in touch with nature at Sunset Beach Park and Waimea Valley. Step out of Haleiwa with an excursion to Dolphin & Whale Watching in Kapolei--about 46 minutes away. The adventure continues: stroll through Sharks Cove and discover the deep blue sea with a scuba or snorkeling tour.

To see maps, traveler tips, reviews, and other tourist information, read our Haleiwa trip itinerary maker website .

Do a combination of flight and bus from Poipu to Haleiwa in 3.5 hours. Expect little chillier evenings in Haleiwa when traveling from Poipu in September, with lows around 24°C. Wrap up your sightseeing on the 9th (Mon) to allow time to travel to Kailua-Kona.

Things to do in Haleiwa

Parks Outdoors Beaches

Side Trips

Ko Olina Lagoons, Turtle Bay Beach, Sharks Cove
Find places to stay Sep 6 — 9:
Highlights from your plan
Scuba & Snorkeling
Ko Olina Lagoons ©
Ko Olina Lagoons
Sunset Beach Park ©
Sunset Beach Park

5
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
We've included these beaches for you: Punalu‘U Beach and Papakōlea Green Sand Beach. Get in touch with nature at Pu'uhonua O Honaunau National Historical Park and Thurston Lava Tube (Nahuku). You'll find plenty of places to visit near Kailua-Kona: Swim with Dolphins (in Waikoloa), Jagger Museum (in Volcano) and Hapuna Beach State Recreation Area (in Puako). Next up on the itinerary: trek along Kilauea Iki Trailhead, see what you can catch with a fishing tour, relax in the rural setting at Greenwell Farms, and steep yourself in history at Puako Petroglyph Archaeological Preserve.

To find ratings, photos, other places to visit, and tourist information, read our Kailua-Kona trip planner.

You can do a combination of bus and flight from Haleiwa to Kailua-Kona in 4.5 hours. Traveling from Haleiwa in September, Kailua-Kona is somewhat warmer at night with lows of 28°C. Cap off your sightseeing on the 14th (Sat) early enough to travel to Kihei.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Hawaii Volcanoes National Park, Greenwell Farms, Hapuna Beach State Recreation Area, Scuba & Snorkeling, Punalu‘U Beach
Find places to stay Sep 9 — 14:
Highlights from your plan
Punalu‘U Beach ©
Punalu‘U Beach
Hapuna Beach State Recreation Area ©
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead

3
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Kick off your visit on the 15th (Sun): stroll through Ulua Beach, stroll through Maluaka Beach, and then enjoy the sand and surf at Makena Beach. On the 16th (Mon), you'll have a packed day of sightseeing: enjoy the sand and surf at Ho'okipa Beach Park, then brush up on your knowledge of spirits at Ocean Vodka Organic Farm and Distillery, then enjoy the sand and surf at Kamaole Beach Park III, and finally enjoy the sand and surf at Kamaole Beach Park II.

Plan my Kihei trip by asking Inpirock to come up with tips and suggestions.

Traveling by combination of flight and bus from Kailua-Kona to Kihei takes 5 hours. Alternatively, you can do a combination of flight and car. In September, daily temperatures in Kihei can reach 38°C, while at night they dip to 26°C. On the 17th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Kihei

Outdoors Beaches Parks

Side Trips

Wailea, Ocean Vodka Organic Farm and Distillery, Ho'okipa Beach Park
Find places to stay Sep 14 — 17:
Highlights from your plan
Ulua Beach ©
Ulua Beach
Wailea Beach Path ©
Wailea Beach Path
Ho'okipa Beach Park ©
Ho'okipa Beach Park

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