14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

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1
Kihei, Maui
— 4 nights
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2
Hanalei, Kauai
— 2 nights
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3
Honolulu, Oahu
— 7 nights
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Kihei, Maui

— 4 nights
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.
Your itinerary includes some good beach time at Ho'okipa Beach Park and Makena Beach. Discover out-of-the-way places like Wailea Beach and Ocean Vodka Organic Farm and Distillery. You'll find plenty of places to visit near Kihei: Napili Beach (in Lahaina) and Kapalua Beach (in Kapalua). There's lots more to do: enjoy the sand and surf at Kamaole Beach Park II, tour the pleasant surroundings at Little Beach, let your taste buds guide you at Maui Pineapple Tours, and see majestic marine mammals with Maui Kayaks.

For reviews, traveler tips, where to stay, and more tourist information, use the Kihei sightseeing site.

New York City to Kihei is an approximately 12.5-hour flight. The time zone difference moving from Eastern Standard Time to Hawaii-Aleutian Standard Time is minus 5 hours. Expect somewhat warmer temperatures when traveling from New York City in September; daily highs in Kihei reach 90°F and lows reach 72°F. Finish your sightseeing early on the 5th (Mon) so you can fly to Hanalei.

Things to do in Kihei

Outdoors · Beaches · Parks · Tours

Side Trips

Hanalei, Kauai

— 2 nights
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Kick off your visit on the 6th (Tue): enjoy the sand and surf at Ke'e Beach, take in the architecture and atmosphere at Wai`oli Hui`ia Church, then take a memorable drive along Hanalei Valley Lookout, and finally kick back and relax at Hanalei Beach. On the 7th (Wed), you'll have a packed day of sightseeing: shop like a local with Michal - Art Studio & Boutique of Hanalei, immerse yourself in nature at Na Pali Coast State Park, and then see some colorful creatures with a scuba or snorkeling tour.

For traveler tips, ratings, where to stay, and tourist information, read our Hanalei trip maker app.

You can fly from Kihei to Hanalei in 2.5 hours. Expect a daytime high around 86°F in September, and nighttime lows around 76°F. Finish up your sightseeing early on the 7th (Wed) so you can catch the flight to Honolulu.

Things to do in Hanalei

Outdoors · Parks · Wildlife · Beaches

Side Trips

Honolulu, Oahu

— 7 nights

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.
You'll explore the less-touristy side of things at Swim with Dolphins and Ala Moana Center. Shop till you drop at Ko Hana Distillers and Haleiwa Town Center. You'll find plenty of places to visit near Honolulu: Lanikai Beach (in Kailua), Byodo-In Temple (in Kaneohe) and Ko Olina Lagoons (in Kapolei). Next up on the itinerary: stroll through Waikiki Beach, kick back and relax at Sharks Cove, stroll the grounds of National Memorial Cemetery of the Pacific, and appreciate the history behind USS Arizona Memorial.

To see where to stay, maps, traveler tips, and other tourist information, use the Honolulu day trip site.

You can fly from Hanalei to Honolulu in 2.5 hours. In September, daily temperatures in Honolulu can reach 88°F, while at night they dip to 76°F. Wrap up your sightseeing on the 14th (Wed) to allow time to fly back home.

Things to do in Honolulu

Outdoors · Beaches · Parks · Shopping

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.