22 days in Hawaii Itinerary

22 days in Hawaii Itinerary

Created using Inspirock Hawaii journey builder

Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 2 nights
Drive
2
Hilo, Island of Hawaii
— 1 night
Fly
3
Lahaina, Maui
— 6 nights
Drive
4
Kihei, Maui
— 2 nights
Fly
5
Honolulu, Oahu
— 3 nights
Fly
6
Lihue, Kauai
— 7 nights
Fly

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Kailua-Kona, Island of Hawaii

— 2 nights

Heart of the Kona Coast

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.
On the 9th (Mon), steep yourself in history at The Painted Church, then admire the sheer force of Rainbow Falls, and then admire all the interesting features of Mauna Loa Scenic Drive.

To find photos, ratings, other places to visit, and tourist information, you can read our Kailua-Kona trip itinerary planning tool.

Oklahoma City to Kailua-Kona is an approximately 12.5-hour flight. The time zone changes from Central Standard Time to Hawaii-Aleutian Standard Time, which is usually a -4 hour difference. When traveling from Oklahoma City in October, plan for a bit warmer days in Kailua-Kona, with highs around 86°F, while nights are warmer with lows around 75°F. You'll have a few hours on the 11th (Wed) to wrap things up before traveling to Hilo.

Things to do in Kailua-Kona

Outdoors · Parks · Scenic Drive · Historic Sites

Side Trips

Hilo, Island of Hawaii

— 1 night

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.
Here are some ideas for day two: admire the natural beauty at Hawaii Tropical Botanical Garden, then take in the dramatic scenery at Akaka Falls State Park, and then take in nature's colorful creations at Liliuokalani Gardens.

For reviews, other places to visit, and more tourist information, read our Hilo trip planner.

You can drive from Kailua-Kona to Hilo in 2 hours. Another option is to take a bus. Traveling from Kailua-Kona in October, plan for a bit cooler nights in Hilo, with lows around 70°F. Finish your sightseeing early on the 12th (Thu) so you can travel to Lahaina.

Things to do in Hilo

Parks · Nature · Wildlife

Side Trip

Lahaina, Maui

— 6 nights

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.
Explore the numerous day-trip ideas around Lahaina: Maui Veterans Cemetery (in Makawao), Haleakala Crater (in Haleakala National Park) and Kalepolepo Beach Park (in Kihei). Spend the 15th (Sun) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: get interesting insight from Tours, enjoy the sand and surf at Kapalua Beach, stroll through Ka'anapali Beach, and admire the majestic nature at Iao Valley.

To find traveler tips, more things to do, ratings, and other tourist information, refer to the Lahaina holiday maker site.

Traveling by flight from Hilo to Lahaina takes 3.5 hours. Alternatively, you can fly. Expect a daytime high around 84°F in October, and nighttime lows around 73°F. Wrap up your sightseeing on the 18th (Wed) early enough to drive to Kihei.

Things to do in Lahaina

Parks · Outdoors · Beaches · Scenic Drive

Side Trips

Kihei, Maui

— 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.
Start off your visit on the 19th (Thu): see the world from above with a helicopter tour, don't miss a visit to Maui Dharma Center, make a trip to Paia Peace Stupa, then contemplate the long history of Haiku Mill, then kick back and relax at Ho'okipa Beach Park, and finally whizz through the canopy at some of the top local zipline courses and adventure parks. Keep things going the next day: enjoy the sand and surf at Kamaole Beach Park II, enjoy the sand and surf at Kamaole Beach Park III, and then tour the pleasant surroundings at Wailea Beach.

Find out how to plan Kihei trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Lahaina to Kihei takes an hour. Alternatively, you can take a bus. In October in Kihei, expect temperatures between 88°F during the day and 70°F at night. Finish your sightseeing early on the 20th (Fri) so you can travel to Honolulu.

Things to do in Kihei

Outdoors · Beaches · Parks · Tours

Side Trips

Honolulu, Oahu

— 3 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.
Go for a jaunt from Honolulu to Kailua to see Kailua Beach Park about 32 minutes away. And it doesn't end there: appreciate the history behind USS Arizona Memorial, take a tour of Battleship Missouri Memorial, see the interesting displays at USS Bowfin Submarine Museum & Park, and meet the residents at Honolulu Zoo.

To find more things to do, other places to visit, traveler tips, and tourist information, read Honolulu trip itinerary maker tool.

Traveling by flight from Kihei to Honolulu takes 3 hours. Alternatively, you can fly. October in Honolulu sees daily highs of 87°F and lows of 74°F at night. Finish your sightseeing early on the 23rd (Mon) so you can travel to Lihue.

Things to do in Honolulu

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Lihue, Kauai

— 7 nights
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 Na Pali Coast State Park (in Wainiha) and Waimea (Waimea Canyon State Park & Aunty Liliko'i). There's still lots to do: kick back and relax at Poipu Beach Park, tour the pleasant surroundings at Tunnels Beach, and take in the dramatic scenery at Opaekaa Falls.

To find photos, traveler tips, ratings, and more tourist information, read our Lihue online route planner.

You can fly from Honolulu to Lihue in 2.5 hours. Alternatively, you can fly. In October, daytime highs in Lihue are 84°F, while nighttime lows are 74°F. You will leave for home on the 30th (Mon).

Things to do in Lihue

Parks · Beaches · Outdoors · Nature

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.