21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

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Route & dates

21 days in Hawaii Itinerary

Start: Toronto
Fly:  14​h 45​min
1
Lihue, Kauai
— 3 nights
Fly:  2​h 30​min
2
Kailua-Kona, Island of Hawaii
— 4 nights
Fly:  4​h
3
Lahaina, Maui
— 5 nights
Fly:  3​h 15​min
4
Honolulu, Oahu
— 8 nights
Fly:  13​h 30​min
End: Toronto

3
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Escape the urban bustle at Waimea Canyon State Park and Dolphin & Whale Watching. You'll enjoy a bit of beach vacationing at Poipu Beach Park and Hanalei Beach. Explore Lihue's surroundings by going to Hanalei Valley Lookout (in Hanalei) and Na Pali Coast State Park (in Wainiha). There's lots more to do: kick back and relax at Shipwreck Beach, contemplate the waterfront views at Menehune Fishpond, explore the striking landscape at Spouting Horn, and take in the dramatic scenery at Opaekaa Falls.

To find reviews, photos, maps, and tourist information, refer to the Lihue route tool .

Toronto, Canada to Lihue is an approximately 15-hour flight. You can also do a combination of train, car, and flight. The time zone difference when traveling from Toronto to Lihue is minus 5 hours. Traveling from Toronto in December, things will get warmer in Lihue: highs are around 30°C and lows about 22°C. Wrap up your sightseeing on the 31st (Thu) early enough to travel to Kailua-Kona.

Things to do in Lihue

Parks Outdoors Beaches

Side Trips

Poipu, Hanalei, Kauai, Na Pali Coast State Park, Waimea Canyon State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Poipu Beach Park ©
Poipu Beach Park

4
nights
Kailua-Kona, Island of Hawaii

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.
You'll get in some beach time at Hapuna Beach State Recreation Area and Papakōlea Green Sand Beach. Kids will enjoy Pu'uhonua O Honaunau National Historical Park and Puukohola National Historic Park. Venture out of the city with trips to Hilo (Liliuokalani Gardens, Rainbow Falls, & more), Laupahoehoe Beach Park (in Laupahoehoe) and Kula Kai Caverns (in Ocean View). Next up on the itinerary: fulfill a lifelong dream with a swim-with-the-dolphins experience, stroll through Mauna Kea Beach, relax in the rural setting at Kona Coffee Living History Farm, and get engrossed in the history at H.N. Greenwell Store Museum.

To find traveler tips, ratings, more things to do, and more tourist information, read our Kailua-Kona trip builder app .

Traveling by flight from Lihue to Kailua-Kona takes 2.5 hours. In December in Kailua-Kona, expect temperatures between 32°C during the day and 24°C at night. Wrap up your sightseeing on the 4th (Mon) to allow time to travel to Lahaina.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Hilo, H.N. Greenwell Store Museum, Kona Coffee Living History Farm, Hapuna Beach State Recreation Area, Mauna Kea Beach
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©

5
nights
Lahaina, Maui

Lahaina ©
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.
Family-friendly places like Ka'anapali Beach and Maui Ocean Center will thrill your kids. Your itinerary includes some good beach time at Wailea Beach and Kalepolepo Beach Park. Explore the numerous day-trip ideas around Lahaina: Wailea Beach Path (in Wailea), Haleakala Crater (in Haleakala National Park) and Ho'okipa Beach Park (in Paia). The adventure continues: cruise along Hana Highway - Road to Hana, make a trip to Lahaina Banyan Court, enjoy the sand and surf at Kapalua Beach, and see majestic marine mammals with a dolphin and whale watching tour.

To see maps, photos, ratings, and more tourist information, refer to the Lahaina trip planner .

You can fly from Kailua-Kona to Lahaina in 4 hours. Other options are to do a combination of taxi, flight, and bus; or do a combination of flight and bus. In January, daily temperatures in Lahaina can reach 30°C, while at night they dip to 22°C. Finish your sightseeing early on the 9th (Sat) so you can travel to Honolulu.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailuku, Wailea, Kapalua Beach, Hana Highway - Road to Hana, Haleakala Crater
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Haleakala Crater ©
Haleakala Crater
Wailea Beach ©
Wailea Beach

8
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get some historical perspective at USS Arizona Memorial and Makapuu Lighthouse Trail. Kids will enjoy Diamond Head State Monument and Sunset Beach Park. Get out of town with these interesting Honolulu side-trips: Swim with Dolphins (in Waianae), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Kailua (Kailua Beach Park & Lanikai Beach). The adventure continues: kick back and relax at Waikiki Beach, take in the dramatic scenery at Manoa Falls, contemplate the long history of Iolani Palace, and contemplate the waterfront views at Hanauma Bay Nature Preserve.

To see maps, photos, more things to do, and more tourist information, refer to the Honolulu trip maker tool .

You can fly from Lahaina to Honolulu in 3.5 hours. Other options are to do a combination of ferry and flight; or do a combination of bus and flight. In January, plan for daily highs up to 32°C, and evening lows to 22°C. Finish up your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Kailua, Haleiwa, Turtle Bay Beach, Pu’u O Mahuka Heiau State Monument, Swim with Dolphins
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Kailua Beach Park ©
Kailua Beach Park

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