14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
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1
Kailua-Kona, Island of Hawaii
— 2 nights
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2
Kihei, Maui
— 3 nights
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3
Hanalei, Kauai
— 3 nights
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4
Honolulu, Oahu
— 5 nights
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Kailua-Kona, Island of Hawaii — 2 nights

Heart of the Kona Coast

Let the collections at Kona Coffee Living History Farm and H.N. Greenwell Store Museum capture your imagination. Get in touch with nature at Pu'uhonua O Honaunau National Historical Park and 49 Black Sand Beach. Get out of town with these interesting Kailua-Kona side-trips: Dolphin Quest (in Waikoloa) and Kealakekua Bay (in Captain Cook). Next up on the itinerary: stroll through Magic Sands, experience rural life at Hula Daddy Kona Coffee, get a dose of the wild on a nature and wildlife tour, and enjoy the sand and surf at Manini'owali Beach (Kua Bay).

To find other places to visit, more things to do, traveler tips, and other tourist information, use the Kailua-Kona travel planning tool.

Toronto, Canada to Kailua-Kona is an approximately 16-hour flight. The time zone difference when traveling from Toronto to Kailua-Kona is minus 5 hours. Expect somewhat warmer temperatures when traveling from Toronto in August; daily highs in Kailua-Kona reach 36°C and lows reach 29°C. Finish your sightseeing early on the 23rd (Wed) so you can fly to Kihei.
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Outdoors · Parks · Beaches · Wildlife
Side Trips

Kihei, Maui — 3 nights

Do some cultural sightseeing at Maria Lanakila Catholic Church and Saint Theresa Roman Catholic Church. You'll get in some beach time at Ahihi Bay and Palauea Beach. Explore Kihei's surroundings by going to Lahaina (Baby Beach, Lahaina Printsellers, &more). There's lots more to do: enjoy the sand and surf at Pa'ako Beach (Secret Cove), explore the striking landscape at Lava Fields, soothe aching muscles at some of the top local wellness centers, and stroll through Kamaole Beach Park I.

For reviews, more things to do, photos, and more tourist information, use the Kihei online trip itinerary planner.

Traveling by flight from Kailua-Kona to Kihei takes 2.5 hours. August in Kihei sees daily highs of 38°C and lows of 26°C at night. Wrap up your sightseeing on the 26th (Sat) to allow time to fly to Hanalei.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips

Hanalei, Kauai — 3 nights

Relax by the water at Secret Beach and Lumahai Beach. You'll explore the less-touristy side of things at Koke'e Mountains and Boat Tours & Water Sports. Explore the numerous day-trip ideas around Hanalei: Kekaha (Kokee Natural History Museum & Awa'awapuhi Trail Parking).

Take the guesswork out of planning a Hanalei vacation by using our trip itinerary maker.

Traveling by flight from Kihei to Hanalei takes 2.5 hours. In August in Hanalei, expect temperatures between 35°C during the day and 28°C at night. Wrap up your sightseeing on the 29th (Tue) to allow time to fly to Honolulu.
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Parks · Outdoors · Nature · Beaches
Side Trips

Honolulu, Oahu — 5 nights

Big Pineapple

Epic Aloha and Queen Emma Summer Palace will appeal to museum buffs. Your itinerary includes some good beach time at Kuhio Beach and White Plains Beach. Get out of town with these interesting Honolulu side-trips: Haleiwa (Kayaking & Canoeing & Shark's Cove), Horseback Riding Tours (in Kahuku) and Banzai Pipeline (in Pupukea). The adventure continues: take in the spiritual surroundings of Saint Augustine by-the-Sea, kick back and relax at Paradise Cove Beach, tour the pleasant surroundings at Sans Souci Beach Park, and savor a delicious cup with a coffee and tea tour.

To find where to stay, ratings, other places to visit, and other tourist information, read Honolulu trip website.

Traveling by flight from Hanalei to Honolulu takes 2.5 hours. In August, daily temperatures in Honolulu can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 3rd (Sun) so you can fly back home.
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Outdoors · Parks · Beaches · Tours
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.
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