17 days in Hawaii Itinerary

17 days in Hawaii Itinerary

Created using Inspirock Hawaii holiday planner
Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 2 nights
Fly
2
Lahaina, Maui
— 3 nights
Fly
3
Hanalei, Kauai
— 3 nights
Drive
4
Koloa, Kauai
— 2 nights
Fly
5
Honolulu, Oahu
— 6 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.
Get some historical perspective at Pu'uhonua O Honaunau National Historical Park and Kealakekua Bay. Relax by the water at Hapuna Beach State Recreation Area and Manini'owali Beach (Kua Bay). Step out of Kailua-Kona to go to Captain Cook and see The Painted Church, which is approximately 40 minutes away. The adventure continues: cast your line with a fishing tour, get engrossed in the history at H.N. Greenwell Store Museum, and stop by Mountain Thunder Coffee Plantation.

To find more things to do, where to stay, reviews, and more tourist information, you can read our Kailua-Kona holiday maker app.

Washington DC to Kailua-Kona is an approximately 14-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Washington DC to Kailua-Kona. Expect somewhat warmer weather when traveling from Washington DC in October: highs in Kailua-Kona hover around 86°F, while lows dip to 75°F. Wrap up your sightseeing on the 13th (Thu) to allow time to fly to Lahaina.
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Find places to stay Oct 11 — 13:

Lahaina, Maui — 3 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.
Take a break from the city and head to Zipline and Kapalua Coastal Trail. Eschew the tourist crowds and head to Ho'okipa Beach Park and Kamaole Beach Park II. When in Lahaina, make a side trip to see Makena Beach in Wailea, approximately Wailea away. Next up on the itinerary: kick back and relax at D.T. Fleming Park, tour the pleasant surroundings at Kapalua Beach, stop by Maui Pineapple Store, and fly like a bird with a parasailing or paragliding tour.

For traveler tips, reviews, more things to do, and other tourist information, use the Lahaina travel itinerary planner.

Fly from Kailua-Kona to Lahaina in 2.5 hours. In October, daily temperatures in Lahaina can reach 84°F, while at night they dip to 73°F. Wrap up your sightseeing on the 16th (Sun) early enough to fly to Hanalei.
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Find places to stay Oct 13 — 16:

Hanalei, Kauai — 3 nights

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. We've included these beaches for you: Ke'e Beach and Hanalei Beach. Get in touch with nature at Na Pali Coast State Park and Kalalau Trail. Next up on the itinerary: discover the deep blue sea with a scuba or snorkeling tour, take in nature's colorful creations at Princeville Botanical Gardens, kick back and relax at Tunnels Beach, and stroll through Anini Beach.

To see more things to do, reviews, photos, and tourist information, refer to the Hanalei road trip planning website.

Getting from Lahaina to Hanalei by flight takes about 2.5 hours. In October, daily temperatures in Hanalei can reach 84°F, while at night they dip to 74°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to drive to Koloa.
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Find places to stay Oct 16 — 19:

Koloa, Kauai — 2 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. On the 20th (Thu), take in the views from Swinging Bridge, experience rural life at Kauai Coffee Company, then identify plant and animal life at Wildlife Areas, and finally enjoy the sand and surf at Poipu Beach Park. On the 21st (Fri), you'll have a packed day of sightseeing: take an in-depth tour of Kauai Museum, then tour the pleasant surroundings at Kalapaki Beach, then admire the sheer force of Wailua Falls, and finally stop by Kauai Nut Roasters.

To see traveler tips, reviews, maps, and other tourist information, you can read our Koloa online driving holiday planner.

You can drive from Hanalei to Koloa in 1.5 hours. Another option is to take a bus. In October, daily temperatures in Koloa can reach 84°F, while at night they dip to 74°F. Finish your sightseeing early on the 21st (Fri) so you can fly to Honolulu.
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Find places to stay Oct 19 — 21:

Honolulu, Oahu — 6 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 get in some beach time at Lanikai Beach and Kailua Beach Park. Discover out-of-the-way places like USS Bowfin Submarine Museum & Park and National Memorial Cemetery of the Pacific. When in Honolulu, make a side trip to see Ko Olina Lagoons in Ko Olina, approximately Ko Olina away. And it doesn't end there: hike along Makapuu Lighthouse Trail, surround yourself with nature on a nature and wildlife tour, tour the pleasant surroundings at Koko Crater Railway Trail, and explore the striking landscape at Halona Blowhole.

To find other places to visit, maps, photos, and other tourist information, read our Honolulu trip planner.

Fly from Koloa to Honolulu in 2.5 hours. In October, plan for daily highs up to 87°F, and evening lows to 74°F. Finish your sightseeing early on the 27th (Thu) so you can fly back home.
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Find places to stay Oct 21 — 27:

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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