19 days in Hawaii Itinerary

19 days in Hawaii Itinerary

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Route & dates

19 days in Hawaii Itinerary

Start: Toronto
Fly:  15​h 15​min
1
Poipu, Kauai
— 2 nights
Fly:  2​h 45​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
— 7 nights
Fly:  13​h 30​min
End: Toronto

2
nights
Poipu, Kauai

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. On the 17th (Tue), take in breathtaking views at Waimea Canyon State Park, then admire the majestic nature at Wailua River State Park, and then take an unforgettable tour with a helicopter tour. Here are some ideas for day two: identify plant and animal life at Wildlife Areas, then kick back and relax at Poipu Beach Park, and then take in the dramatic natural features at Spouting Horn.

Before you visit Poipu, use our trip planner to discover what you can do and see there.

Toronto, Canada to Poipu is an approximately 15.5-hour flight. You can also do a combination of train, car, and flight. The time zone difference moving from Eastern Standard Time (EST) to Hawaii Standard Time (HST) is minus 5 hours. Prepare for much warmer weather when traveling from Toronto in December: high temperatures in Poipu hover around 30°C and lows are around 22°C. Finish your sightseeing early on the 18th (Wed) so you can travel to Kailua-Kona.

Things to do in Poipu

Parks Nature Tours

Side Trips

Waimea Canyon State Park, Wailua River State Park, Helicopter Tours
Highlights from your plan
Waimea Canyon State Park ©
Waimea Canyon State Park
Poipu Beach Park ©
Poipu Beach Park
Helicopter Tours

4
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
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.
Explore the numerous day-trip ideas around Kailua-Kona: Hilo (Akaka Falls State Park & Liliuokalani Gardens), Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Devastation Trail, & more) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). There's still lots to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, stroll through Hapuna Beach State Recreation Area, take in the exciting artwork at Hawaii Cigar & Ukulele, and admire the verdant scenery at Pololu Valley Lookout.

To find ratings, reviews, other places to visit, and more tourist information, read Kailua-Kona trip maker app .

Fly from Poipu to Kailua-Kona in 3 hours. December in Kailua-Kona sees daily highs of 32°C and lows of 24°C at night. Finish up your sightseeing early on the 22nd (Sun) so you can travel to Lahaina.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Hilo, H.N. Greenwell Store Museum, Pololu Valley Lookout, Pu'uhonua O Honaunau National Historical Park
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Swim with Dolphins
Akaka Falls State Park ©
Akaka Falls State Park

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.
Explore Lahaina's surroundings by going to Haleakala Crater (in Haleakala National Park), Ho'okipa Beach Park (in Paia) and Kalepolepo Beach Park (in Kihei). There's still lots to do: take a memorable drive along Hana Highway - Road to Hana, wander the streets of Lahaina Front Street, admire the majestic nature at Iao Valley, and take a tour by water with Boat Tours & Water Sports.

To see other places to visit, more things to do, reviews, and other tourist information, read our Lahaina trip itinerary tool .

Traveling by flight from Kailua-Kona to Lahaina takes 4 hours. Alternatively, you can do a combination of taxi, flight, and bus; or do a combination of flight and bus. Expect a daytime high around 30°C in December, and nighttime lows around 23°C. Finish up your sightseeing early on the 27th (Fri) so you can travel to Honolulu.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailuku, Kalepolepo Beach Park, Hana Highway - Road to Hana, Wailea Beach, Ho'okipa Beach Park
Highlights from your plan
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater
Maui Ocean Center ©
Maui Ocean Center

7
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.
You'll find plenty of places to visit near Honolulu: Kailua Beach Park (in Kailua), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Haleiwa (Sunset Beach Park & Waimea Bay). The adventure continues: kick back and relax at Waikiki Beach, take a stroll around Polynesian Cultural Center, stroll the grounds of USS Arizona Memorial, and contemplate the long history of Iolani Palace.

For other places to visit, traveler tips, and more tourist information, read our Honolulu trip itinerary builder site .

Traveling by flight from Lahaina to Honolulu takes 3.5 hours. Alternatively, you can do a combination of ferry and flight; or do a combination of bus and flight. In December in Honolulu, expect temperatures between 32°C during the day and 24°C at night. Finish your sightseeing early on the 3rd (Fri) to allow enough time to travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Polynesian Cultural Center, Pu’u O Mahuka Heiau State Monument, Kailua Beach Park
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

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