20 days in Hawaii Itinerary

20 days in Hawaii Itinerary

Created using Inspirock Hawaii vacation planner

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Route & dates

20 days in Hawaii Itinerary

Start: Tokyo
Fly:  9​h 45​min
1
Honolulu, Oahu
— 5 nights
Fly:  3​h 15​min
2
Lahaina, Maui
— 5 nights
bus + Fly:  3​h 15​min
3
Hilo, Island of Hawaii
— 3 nights
Drive:  1​h 45​min
4
Kailua-Kona, Island of Hawaii
— 2 nights
Fly:  2​h 30​min
5
Lihue, Kauai
— 3 nights
Fly:  12​h
End: Tokyo

5
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: Haleiwa (Sunset Beach Park & Waimea Bay), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Kailua Beach Park (in Kailua). There's lots more to do: explore the different monuments and memorials at USS Arizona Memorial, browse the different shops at Ala Moana Center, kick back and relax at Waikiki Beach, and explore the activities along Hanauma Bay Nature Preserve.

To find traveler tips, ratings, reviews, and other tourist information, read our Honolulu trip itinerary planning tool .

Tokyo, Japan to Honolulu is an approximately 10-hour flight. You can also do a combination of train and flight. The time zone difference moving from Japan Standard Time to Hawaii Standard Time is minus 19 hours. Plan for somewhat warmer temperatures traveling from Tokyo in October, with highs in Honolulu at 36°C and lows at 27°C. Wrap up your sightseeing on the 16th (Wed) early enough to travel to Lahaina.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Kailua Beach Park, Pu’u O Mahuka Heiau State Monument
Find places to stay Oct 10 — 16:
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

5
nights
Lahaina, Maui

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.
You'll find plenty of places to visit near Lahaina: Haleakala Crater (in Haleakala National Park), Iao Valley (in Wailuku) and Kalepolepo Beach Park (in Kihei). And it doesn't end there: cruise along Hana Highway - Road to Hana, take an in-depth tour of Baldwin Home Museum, discover the deep blue sea with a scuba or snorkeling tour, and stroll through Ka'anapali Beach.

To see ratings, more things to do, reviews, and other tourist information, you can read our Lahaina day trip planner.

Fly from Honolulu to Lahaina in 3.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight and bus. In October, daytime highs in Lahaina are 34°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 21st (Mon) early enough to travel to Hilo.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailuku, Maui, Wailea Beach, Kalepolepo Beach Park, Haleakala Crater
Find places to stay Oct 16 — 21:
Highlights from your plan
Scuba & Snorkeling
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater

3
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.
Get out of town with these interesting Hilo side-trips: Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Kipuka Puaulu (Bird Park) Trail, & more). There's still lots to do: admire the majestic nature at Akaka Falls State Park, admire the natural beauty at Liliuokalani Gardens, and stop by Hilo Coffee Mill.

To see maps, traveler tips, where to stay, and tourist information, refer to the Hilo online holiday planner .

You can do a combination of bus and flight from Lahaina to Hilo in 3.5 hours. Other options are to fly; or do a combination of bus and flight. Expect a daytime high around 34°C in October, and nighttime lows around 24°C. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Hilo Coffee Mill, Jagger Museum
Find places to stay Oct 21 — 24:
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Liliuokalani Gardens ©
Liliuokalani Gardens
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

2
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.
Start off your visit on the 25th (Fri): browse the exhibits of Kona Coffee Living History Farm, explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, then enjoy the sand and surf at Kahaluu Beach, and finally get close to the beloved marine mammals with a swim-with-the-dolphins experience. Get ready for a full day of sightseeing on the 26th (Sat): kick back and relax at Hapuna Beach State Recreation Area and then kick back and relax at Mauna Kea Beach.

For more things to do, where to stay, maps, and more tourist information, use the Kailua-Kona road trip planning website .

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In October in Kailua-Kona, expect temperatures between 35°C during the day and 28°C at night. Cap off your sightseeing on the 26th (Sat) early enough to travel to Lihue.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Hapuna Beach State Recreation Area, Pu'uhonua O Honaunau National Historical Park, Mauna Kea Beach, Kona Coffee Living History Farm, Kahaluu Beach
Find places to stay Oct 24 — 26:
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

3
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Explore the numerous day-trip ideas around Lihue: Waimea Canyon State Park (in Waimea), Hanalei Beach (in Hanalei) and Na Pali Coast State Park (in Wainiha). There's still lots to do: kick back and relax at Poipu Beach Park, take an unforgettable tour with a helicopter tour, take in the dramatic natural features at Spouting Horn, and paddle through the water with a kayaking and canoeing tour.

To find reviews and more tourist information, refer to the Lihue online tour planner .

Traveling by flight from Kailua-Kona to Lihue takes 2.5 hours. In October, daytime highs in Lihue are 34°C, while nighttime lows are 27°C. Cap off your sightseeing on the 29th (Tue) early enough to travel back home.

Things to do in Lihue

Parks Tours Outdoors

Side Trips

Kapaa, Poipu, Hanalei Beach, Na Pali Coast State Park, Waimea Canyon State Park
Find places to stay Oct 26 — 29:
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

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