14 days in Hawaii Itinerary

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Kailua-Kona, Island of Hawaii
— 2 nights
Kihei, Maui
— 3 nights
Hanalei, Kauai
— 3 nights
Honolulu, Oahu
— 5 nights


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.
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 Magic Sands. Get out of town with these interesting Kailua-Kona side-trips: Kealakekua Bay (in Captain Cook) and Waikoloa (49 Black Sand Beach & Dolphin Quest). Next up on the itinerary: stroll through Manini'owali Beach (Kua Bay), enjoy the sand and surf at White Sand Beach, get a dose of the wild on a nature and wildlife tour, and experience rural life at Hula Daddy Kona Coffee.

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.
Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Aug 21 — 23:

Kihei, Maui — 3 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.
Do some cultural sightseeing at Maria Lanakila Catholic Church and Maui Hands. You'll get in some beach time at Ahihi Bay and Baby Beach. Step out of Kihei to go to Lahaina and see Lahaina Printsellers, which is approximately 42 minutes away. The adventure continues: kick back and relax at Palauea Beach, tour the pleasant surroundings at Pa'ako Beach (Secret Cove), stroll around Kamaole Beach Park I, and explore the striking landscape at Lava Fields.

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Traveling by flight from Kailua-Kona to Kihei takes 2.5 hours. In August, daily temperatures in Kihei can reach 38°C, while at night they dip to 26°C. Wrap up your sightseeing on the 26th (Sat) early enough to fly to Hanalei.
Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay Aug 23 — 26:

Hanalei, Kauai — 3 nights

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Relax by the water at Secret Beach and Lumahai Beach. You'll explore the less-touristy side of things at Koke'e Mountains and Koke`e State Park. Explore the numerous day-trip ideas around Hanalei: Kekaha (Kokee Natural History Museum & Awa'awapuhi Trail Parking). And it doesn't end there: take a tour by water with Boat Tours & Water Sports, look for gifts at Hanalei Farmer’s Market, tour the pleasant surroundings at Kalihiwai Beach, and look for all kinds of wild species at Hanalei National Wildlife Refuge.

For reviews, other places to visit, photos, and other tourist information, you can read our Hanalei trip itinerary maker app.

You can fly from Kihei to Hanalei in 2.5 hours. In August, daily temperatures in Hanalei can reach 35°C, while at night they dip to 28°C. Finish your sightseeing early on the 29th (Tue) to allow enough time to fly to Honolulu.
Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Aug 26 — 29:

Honolulu, Oahu — 5 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.
Epic Aloha and Queen Emma Summer Palace will appeal to museum buffs. Your itinerary includes some good beach time at Kuhio Beach and Kualoa Regional Park. 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.
Outdoors · Parks · Beaches · Tours
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Find places to stay Aug 29 — Sep 3:

Hawaii travel guide

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.