21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

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Route & dates

21 days in Hawaii Itinerary

Start: Calgary
Fly:  9​h 15​min
1
Lihue, Kauai
— 3 nights
Fly:  2​h 15​min
2
Honolulu, Oahu
— 7 nights
Fly:  3​h 15​min
3
Lahaina, Maui
— 6 nights
Bus + Fly:  3​h 15​min
4
Hilo, Island of Hawaii
— 4 nights
Fly:  9​h 30​min
End: Calgary

3
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Venture out of the city with trips to Waimea Canyon State Park (in Waimea), Hanalei (Hanalei Beach & Hanalei Valley Lookout) and Na Pali Coast State Park (in Wainiha). And it doesn't end there: kick back and relax at Poipu Beach Park, capture your vacation like a pro with an inspiring photography tour, take an unforgettable tour with a helicopter tour, and look for gifts at Kapaia Stitchery.

To find ratings, more things to do, maps, and other tourist information, read Lihue trip maker site .

Calgary, Canada to Lihue is an approximately 9.5-hour flight. Traveling from Calgary to Lihue, you'll gain 3 hours due to the time zone difference. Prepare for much hotter weather when traveling from Calgary in January: high temperatures in Lihue hover around 30°C and lows are around 21°C. Finish up your sightseeing early on the 9th (Thu) so you can travel to Honolulu.

Things to do in Lihue

Parks Nature Tours

Side Trips

Hanalei, Poipu, Waimea Canyon State Park, Photography Tours, Opaekaa Falls
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Poipu Beach Park ©
Poipu Beach Park
Helicopter Tours

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), Haleiwa (Sunset Beach Park & Waimea Bay) and Pu’u O Mahuka Heiau State Monument (in Pupukea). Next up on the itinerary: stroll the grounds of USS Arizona Memorial, buy something for everyone on your list at Ala Moana Center, take a stroll around Polynesian Cultural Center, and examine the collection at Bishop Museum.

To find photos, traveler tips, ratings, and other tourist information, you can read our Honolulu attractions planner.

Traveling by flight from Lihue to Honolulu takes 2.5 hours. January in Honolulu sees daily highs of 32°C and lows of 22°C at night. Finish up your sightseeing early on the 16th (Thu) so you can travel to Lahaina.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

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

6
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 Kihei (Kalepolepo Beach Park & Stand-Up Paddleboarding), Wailea Beach (in Wailea) and Haleakala Crater (in Haleakala National Park). There's lots more to do: take a memorable drive along Hana Highway - Road to Hana, don't miss a visit to Lahaina Banyan Court, get up close to creatures of the deep with a dolphin and whale watching tour, and get up close and personal with brilliant marine life at Maui Ocean Center.

To see photos, reviews, maps, and more tourist information, go to the Lahaina trip planner .

Getting from Honolulu to Lahaina by flight takes about 3.5 hours. Other options: do a combination of flight and ferry; or do a combination of flight and bus. In January, daytime highs in Lahaina are 30°C, while nighttime lows are 22°C. Cap off your sightseeing on the 22nd (Wed) early enough to travel to Hilo.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailuku, Kalepolepo Beach Park, Haleakala Crater, Kapalua Resort, Hana Highway - Road to Hana
Highlights from your plan
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater
Maui Ocean Center ©
Maui Ocean Center

4
nights
Hilo, Island of Hawaii

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
You'll find plenty of places to visit near Hilo: Kona Coffee Living History Farm (in Captain Cook), Swim with Dolphins (in Kailua-Kona) and Hawaii Volcanoes National Park (Kilauea Iki Trailhead & Kipuka Puaulu (Bird Park) Trail). The adventure continues: admire the sheer force of Akaka Falls State Park, take in nature's colorful creations at Liliuokalani Gardens, admire the majestic nature at Hapuna Beach State Recreation Area, and steep yourself in history at Puukohola National Historic Park.

To see ratings, photos, reviews, and tourist information, refer to the Hilo trip planner.

Traveling by combination of bus and flight from Lahaina to Hilo takes 3.5 hours. Alternatively, you can fly; or do a combination of bus and flight. In January, plan for daily highs up to 32°C, and evening lows to 20°C. You'll have a few hours on the 26th (Sun) to wrap things up before traveling home.

Things to do in Hilo

Outdoors Parks Nature

Side Trips

Hawaii Volcanoes National Park, Kona Coffee Living History Farm, Swim with Dolphins, Puukohola National Historic Park, Hapuna Beach State Recreation Area
Highlights from your plan
Swim with Dolphins
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Akaka Falls State Park ©
Akaka Falls State Park

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