20 days in Hawaii Itinerary

20 days in Hawaii Itinerary

Created using Inspirock United States trip planner
Make it your trip
Fly
1
Kahului
— 2 nights
Drive
2
Kihei
— 2 nights
Fly
3
Honolulu, Oahu
— 4 nights
Fly
4
Hanalei, Kauai
— 4 nights
Drive
5
Koloa, Kauai
— 2 nights
Fly
6
Captain Cook, Island of Hawaii
— 3 nights
Fly
7
Lahaina
— 1 night
Drive
8
Kahului
— 1 night
Fly

S M T W T F S
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Kahului — 2 nights

Kahului is a census-designated place (CDP) in Maui County, on the island of Maui, in the U.S. state of Hawaii. Start off your visit on the 13th (Thu): take some stellar pictures from Epic Experience Maui, then take in the exciting artwork at Maui Crafts Guild, then make a trip to Maui Dharma Center, and finally make a trip to Paia Peace Stupa.

For where to stay, other places to visit, photos, and other tourist information, read our Kahului trip itinerary builder.

Tulsa to Kahului is an approximately 11-hour flight. Traveling from Tulsa to Kahului, you'll gain 4 hours due to the time zone difference. Traveling from Tulsa in October, expect Kahului to be somewhat warmer, temps between 88°F and 70°F. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Kihei.
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Find places to stay Oct 12 — 14:

Kihei — 2 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.
On the 14th (Fri), stroll through Keawakapu Beach, then tour the pleasant surroundings at Kamaole Beach Park II, and then kick back and relax at Kamaole Beach Park III. Keep things going the next day: discover the deep blue sea with a scuba or snorkeling tour, then tour the pleasant surroundings at Wailea Beach Path, and then tour the pleasant surroundings at Polo Beach.

To find reviews, other places to visit, maps, and tourist information, refer to the Kihei trip itinerary builder tool.

Kihei is very close to Kahului. In October in Kihei, expect temperatures between 88°F during the day and 70°F at night. You will leave for Honolulu on the 16th (Sun).
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Outdoors · Parks · Beaches · Tours
Side Trip
Find places to stay Oct 14 — 16:

Honolulu, Oahu — 4 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.
Do some cultural sightseeing at USS Arizona Memorial and National Memorial Cemetery of the Pacific. You'll explore the less-touristy side of things at Lanikai Beach and Scuba & Snorkeling. Explore the numerous day-trip ideas around Honolulu: Pupukea (Shark's Cove & Banzai Pipeline). Next up on the itinerary: see the interesting displays at Pearl Harbor Aviation Museum, take some stellar pictures from Nu’uanu Pali, enjoy the sand and surf at Ala Moana Beach Park, and learn about all things military at US Army Museum of Hawaii.

To find ratings, reviews, where to stay, and other tourist information, use the Honolulu route website.

Traveling by flight from Kihei to Honolulu takes 2.5 hours. In October in Honolulu, expect temperatures between 87°F during the day and 74°F at night. Finish your sightseeing early on the 20th (Thu) to allow enough time to fly to Hanalei.
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Find places to stay Oct 16 — 20:

Hanalei, Kauai — 4 nights

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Relax by the water at Hanalei Beach and Puu Poa Beach. Get in touch with nature at Hanalei Valley Lookout and Hāʻena State Park. And it doesn't end there: kick back and relax at Secret Beach, tour the pleasant surroundings at Kalihiwai Beach, look for gifts at Hanalei Farmer’s Market, and pause for some serene contemplation at Wai`oli Hui`ia Church.

For more things to do, reviews, traveler tips, and tourist information, you can read our Hanalei trip builder app.

Getting from Honolulu to Hanalei by flight takes about 2.5 hours. October in Hanalei sees daily highs of 84°F and lows of 74°F at night. Wrap up your sightseeing on the 24th (Mon) early enough to drive to Koloa.
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Parks · Outdoors · Beaches · Nature
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Find places to stay Oct 20 — 24:

Koloa, Kauai — 2 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Kick off your visit on the 24th (Mon): appreciate the extensive heritage of Old Koloa Town, get a dose of the wild on Kauai Safaris, and then take in the dramatic natural features at Makawehi Bluff. On the next day, view the masterpieces at Art House Hawaii, then kick back and relax at Baby Beach, and then kick back and relax at Lawa'i Beach.

To find where to stay, more things to do, and more tourist information, use the Koloa trip planning website.

Traveling by car from Hanalei to Koloa takes 1.5 hours. Alternatively, you can take a bus. October in Koloa sees daily highs of 84°F and lows of 74°F at night. Finish up your sightseeing early on the 26th (Wed) so you can catch the flight to Captain Cook.
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Outdoors · Parks · Beaches · Neighborhoods
Side Trip
Find places to stay Oct 24 — 26:

Captain Cook, Island of Hawaii — 3 nights

A small town with big ocean views, Captain Cook lies on top of an ancient fault line that was responsible for creating the nearby Kealakekua Bay thousands of years ago.
Pu'uhonua O Honaunau National Historical Park and Kealakekua Bay will appeal to history buffs. Get in touch with nature at Two Step and Kahaluu Beach. Next up on the itinerary: take an in-depth tour of Kona Coffee Living History Farm, relax in the rural setting at Royal Kona Coffee Center, and admire the natural beauty at Paleaku Gardens Peace Sanctuary.

To find maps, ratings, other places to visit, and more tourist information, you can read our Captain Cook trip itinerary maker website.

Fly from Koloa to Captain Cook in 2.5 hours. In October, daytime highs in Captain Cook are 86°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 29th (Sat) to allow time to fly to Lahaina.
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Find places to stay Oct 26 — 29:

Lahaina — 1 night

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.
On the 29th (Sat), take in the exciting artwork at Maui Hands, contemplate the long history of Old Lahaina Courthouse, and then contemplate the waterfront views at Lahaina Harbor. On the 30th (Sun), you'll have a packed day of sightseeing: walk around Lahaina Banyan Court, then take an in-depth tour of Baldwin Home Museum, then look for gifts at Honolulu Cookie Company, and finally tour the pleasant surroundings at Baby Beach.

For ratings, photos, more things to do, and other tourist information, read our Lahaina travel route planner.

You can fly from Captain Cook to Lahaina in 2.5 hours. In October, daytime highs in Lahaina are 84°F, while nighttime lows are 73°F. Cap off your sightseeing on the 30th (Sun) early enough to go by car to Kahului.
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Parks · Shopping · Nature · Outdoors
Find places to stay Oct 29 — 30:

Kahului — 1 night

To find reviews, photos, more things to do, and more tourist information, read Kahului journey planner.

Traveling by car from Lahaina to Kahului takes an hour. Alternatively, you can take a bus. On the 31st (Mon), you'll travel back home.
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Tours · Outdoors · Wildlife · Parks
Find places to stay Oct 30 — 31:

Hawaii travel guide

4.4
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.
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