31 days in Hawaii Itinerary

31 days in Hawaii Itinerary

Created using Inspirock Hawaii planner

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Route & dates

Start: Kingston
+2
Drive + Bus + Fly:  16 h
1
Honolulu, Oahu
— 8 nights
Fly:  2 h 15 min
2
Lihue, Kauai
— 3 nights
Fly:  2 h 15 min
3
Kailua-Kona, Island of Hawaii
— 6 nights
Drive:  2 h
4
Hilo, Island of Hawaii
— 4 nights
Fly + Bus:  3 h 15 min
5
Lahaina, Maui
— 8 nights
Bus + Fly:  16 h 45 min
End: Kingston

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 out of town with these interesting Honolulu side-trips: Kailua Beach Park (in Kailua), Laie (Malaekahana State Recreation Area & Polynesian Cultural Center) and Haleiwa (Sunset Beach Park & Waimea Bay). There's still lots to do: go for a walk through Diamond Head State Monument, buy something for everyone on your list at Ala Moana Center, steep yourself in history at Battleship Missouri Memorial, and explore the activities along Hanauma Bay Nature Preserve.

For where to stay, other places to visit, photos, and other tourist information, refer to the Honolulu sightseeing planning website.

Kingston, Canada to Honolulu is an approximately 16.5- hour flight. You can also do a combination of bus, car, and flight; or do a combination of train and flight. The time zone changes from Eastern Standard Time (EST) to Hawaii Standard Time (HST), which is usually a -5 hour difference. Traveling from Kingston in January, expect Honolulu to be much warmer, temps between 32°C and 22°C. Wrap up your sightseeing on the 9th (Thu) early enough to travel to Lihue.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Laie, Haleiwa, Kailua Beach Park, Kawaiahao Church
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

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), Na Pali Coast State Park (in Wainiha) and Hanalei (Hanalei Valley Lookout & Hanalei Beach). The adventure continues: see the world from above with a helicopter tour, explore the striking landscape at Spouting Horn, admire the sheer force of Opaekaa Falls, and enjoy the sand and surf at Poipu Beach Park.

For maps, reviews, ratings, and other tourist information, use the Lihue planning tool.

Traveling by flight from Honolulu to Lihue takes 2.5 hours. Expect a daytime high around 30°C in January, and nighttime lows around 21°C. Wrap up your sightseeing on the 12th (Sun) early enough to travel to Kailua-Kona.

Things to do in Lihue

Parks Nature Outdoors

Side Trips

Poipu, Hanalei, Wailua River State Park, Waimea Canyon State Park, Na Pali Coast State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Helicopter Tours

6
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.
Change things up with these side-trips from Kailua-Kona: Captain Cook (Kealakekua Bay & Big Island Bees), Papakōlea Green Sand Beach (in Naalehu) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). The adventure continues: fulfill a lifelong dream with a swim-with-the-dolphins experience, play a few rounds at Mauna Lani Resort , enjoy the sand and surf at Mauna Kea Beach, and explore the wealth of natural beauty at Puukohola National Historic Park.

To find maps, other places to visit, where to stay, and more tourist information, use the Kailua-Kona online holiday planner.

Getting from Lihue to Kailua-Kona by flight takes about 2.5 hours. In January, daytime highs in Kailua-Kona are 31°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 18th (Sat) early enough to drive to Hilo.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Island of Hawaii, Captain Cook, Hapuna Beach State Recreation Area, Mauna Lani Resort , Kahaluu Beach
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Mauna Kea Beach ©
Mauna Kea Beach

4
nights
Hilo, Island of Hawaii

Hilo ©
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.
Change things up with these side-trips from Hilo: Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Sulphur Banks, &more) and Jagger Museum (in Volcano). There's much more to do: immerse yourself in nature at Akaka Falls State Park, take in nature's colorful creations at Liliuokalani Gardens, and admire the sheer force of Rainbow Falls.

To find traveler tips, maps, other places to visit, and more tourist information, refer to the Hilo trip planning website.

You can drive from Kailua-Kona to Hilo in 2 hours. Another option is to take a bus. January in Hilo sees daily highs of 32°C and lows of 20°C at night. Finish up your sightseeing early on the 22nd (Wed) so you can travel to Lahaina.

Things to do in Hilo

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Jagger Museum
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

8
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.
Venture out of the city with trips to Haleakala Crater (in Haleakala National Park), Wailuku (Iao Valley & Hale Ho'ike'ike at the Bailey House) and Kamaole Beach Park III (in Kihei). Spend the 23rd (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: walk around Lahaina Banyan Court, take in the architecture and atmosphere at Maria Lanakila Catholic Church, observe the fascinating underwater world at Maui Ocean Center, and enjoy the sand and surf at Ka'anapali Beach.

To find where to stay, photos, other places to visit, and more tourist information, go to the Lahaina route maker app.

Traveling by combination of flight and bus from Hilo to Lahaina takes 3.5 hours. Alternatively, you can fly; or do a combination of bus, taxi, and flight. In January, daily temperatures in Lahaina can reach 30°C, while at night they dip to 22°C. Finish your sightseeing early on the 30th (Thu) to allow enough time to travel back home.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailuku, Kapalua, Haleakala Crater, Wailea Beach, Hana Highway - Road to Hana
Highlights from your plan
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater
Lahaina Banyan Court ©
Lahaina Banyan Court

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