14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii vacation planner

Plan created by another user. Make it yours
Fly
1
Honolulu, Oahu
— 5 nights
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2
Lihue, Kauai
— 3 nights
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3
Lahaina, Maui
— 2 nights
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4
Hilo, Island of Hawaii
— 3 nights
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5
nights
Honolulu, Oahu

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.
Get out of town with these interesting Honolulu side-trips: Pu’u O Mahuka Heiau State Monument (in Pupukea), Haleiwa (Sunset Beach Park, Wys Galleries, &more) and Kailua Beach Park (in Kailua). There's still lots to do: stroll the grounds of USS Arizona Memorial, enjoy the sand and surf at Waikiki Beach, take in the pleasant sights at Diamond Head State Monument, and kick your exploration up a notch at CLIMB Works Keana Farms.

To see reviews, traveler tips, other places to visit, and tourist information, go to the Honolulu trip maker app.

New York City to Honolulu is an approximately 14-hour flight. You'll gain 5 hours traveling from New York City to Honolulu due to the time zone difference. Traveling from New York City in September, expect Honolulu to be a bit warmer, temps between 88°F and 76°F. Finish your sightseeing early on the 2nd (Sat) so you can travel to Lihue.

Things to do in Honolulu

Outdoors · Parks · Beaches · Historic Sites

Side Trips

3
nights
Lihue, Kauai

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Explore Lihue's surroundings by going to Hanalei Beach (in Hanalei), Skydive Kauai (in Hanapepe) and Waimea (Puu Hinahina Lookout & Waimea Canyon State Park). There's much more to do: take a tour by water with Boat Tours & Water Sports, admire the majestic nature at Na Pali Coast State Park, take an unforgettable tour with a helicopter tour, and see Kipu Ranch Adventures.

To find reviews, photos, more things to do, and more tourist information, read our Lihue road trip planner.

You can fly from Honolulu to Lihue in 2.5 hours. In October, daytime highs in Lihue are 84°F, while nighttime lows are 74°F. Cap off your sightseeing on the 5th (Tue) early enough to travel to Lahaina.

Things to do in Lihue

Outdoors · Parks · Tours · Beaches

Side Trips

2
nights
Lahaina, Maui

Crown Jewel of Maui

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.
Start off your visit on the 6th (Wed): appreciate the history behind Lahaina Jodo Mission, then take a memorable tour with Tours, and then kick back and relax at Ka'anapali Beach. On the next day, admire the majestic nature at Iao Valley, observe the fascinating underwater world at Maui Ocean Center, and then walk around Lahaina Banyan Court.

For photos, other places to visit, where to stay, and more tourist information, you can read our Lahaina trip itinerary maker website.

You can fly from Lihue to Lahaina in 3.5 hours. Expect a daytime high around 84°F in October, and nighttime lows around 73°F. Cap off your sightseeing on the 7th (Thu) early enough to travel to Hilo.

Things to do in Lahaina

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trip

3
nights
Hilo, Island of Hawaii

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
On the 8th (Fri), get up close and personal with brilliant marine life at Mokupapapa Discovery Center, stroll through Devastation Trail, then trek along Kilauea Iki Trailhead, and finally hike along Sulphur Banks. Keep things going the next day: admire the natural beauty at Liliuokalani Gardens, then take in the dramatic scenery at Rainbow Falls, then whizz through the canopy at Skyline Hawaii - Big Island Zipline Tours, and finally take in the dramatic scenery at Akaka Falls State Park.

Quickly create a custom-made itinerary for Hilo using our trip planner.

Fly from Lahaina to Hilo in 3.5 hours. Expect a daytime high around 84°F in October, and nighttime lows around 70°F. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel back home.

Things to do in Hilo

Parks · Outdoors · Trails · Nature

Side Trips

Hawaii travel guide

4.3
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.