Route & dates
12 days in Hawaii Itinerary
Start: Santiago
Fly:
9h 30min
1
Honolulu, Oahu
— 4 nights
Fly:
2h 30min
2
Hilo, Island of Hawaii
— 1 night
Drive:
1h 45min
3
Kailua-Kona, Island of Hawaii
— 2 nights
Fly + bus:
5h 30min
4
Wailea, Maui
— 2 nights
Drive:
15min
5
Kihei, Maui
— 1 night
Fly:
22h 30min
End: Santiago
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4
nights
Honolulu, Oahu
4
nights

Big Pineapple
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.Venture out of the city with trips to Kailua Beach Park (in Kailua), Ehukai Beach Park (in Pupukea) and Haleiwa (Waimea Bay & Sunset Beach Park). There's still lots to do: stroll through Diamond Head State Monument, appreciate the history behind King Kamehameha Statue, admire the sheer force of Manoa Falls, and get great views at Puu Ualakaa State Park.
For ratings, more things to do, reviews, and tourist information, use the Honolulu day trip planner .
Santiago, Chile to Honolulu is an approximately 22-hour flight. Traveling from Santiago to Honolulu, you'll gain 6 hours due to the time zone difference. In December, daytime highs in Honolulu are 32°C, while nighttime lows are 24°C. Finish your sightseeing early on the 25th (Fri) so you can travel to Hilo.
Things to do in Honolulu
Side Trips
Haleiwa, Kailua Beach Park, Ehukai Beach Park
Highlights from your plan

Diamond Head State Monument
12:00pm, Tue Dec 22

Waikiki Beach
11:00am, Fri Dec 25

Hanauma Bay Nature Preserve
10:00am, Tue Dec 22
1
night
Hilo, Island of Hawaii
1
night

America's Wettest City
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.Start off your visit on the 26th (Sat): browse the fresh offerings at Hilo Farmers Market, stop by Big Island Candies, then get to know the resident critters at Panaewa Rainforest Zoo and Gardens, then admire the sheer force of Rainbow Falls, and finally take in the architecture and atmosphere at St. Joseph Catholic Church,.
Plan a trip to Hilo easily and quickly by telling Inspirock to suggest an itinerary.
Getting from Honolulu to Hilo by flight takes about 2.5 hours. In December, plan for daily highs up to 31°C, and evening lows to 21°C. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Kailua-Kona.
Things to do in Hilo
Side Trip
Big Island Candies
Highlights from your plan

Hilo Farmers Market
10:00am, Sat Dec 26

Rainbow Falls
3:00pm, Sat Dec 26

Big Island Candies
11:30am, Sat Dec 26
2
nights
Kailua-Kona, Island of Hawaii
2
nights

Heart of the Kona Coast
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.On the 27th (Sun), kick back and relax at Hapuna Beach State Recreation Area and then enjoy the sand and surf at Manini'owali Beach (Kua Bay). Keep things going the next day: experience rural life at Hula Daddy Kona Coffee, then relax in the rural setting at Greenwell Farms, and then steep yourself in history at Pu'uhonua O Honaunau National Historical Park.
For where to stay, traveler tips, reviews, and more tourist information, you can read our Kailua-Kona online trip itinerary builder .
Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In December, daytime highs in Kailua-Kona are 32°C, while nighttime lows are 24°C. Finish your sightseeing early on the 28th (Mon) to allow enough time to travel to Wailea.
Things to do in Kailua-Kona
Side Trips
Pu'uhonua O Honaunau National Historical Park, Hula Daddy Kona Coffee, Greenwell Farms, Hapuna Beach State Recreation Area
Highlights from your plan

Pu'uhonua O Honaunau National Historical Park
2:00pm, Mon Dec 28

Hapuna Beach State Recreation Area
10:30am, Sun Dec 27

Manini'owali Beach (Kua Bay)
2:00pm, Sun Dec 27
2
nights
Wailea, Maui
2
nights

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. On the 29th (Tue), take in the architecture and atmosphere at Keawala'i Congregational Church, identify plant and animal life at Ahihi-Kinau Natural Area Reserve, and then get impressive views of Molokini Crater. On your second day here, kick back and relax at Wailea Beach, then tee off at Wailea Blue Golf Course, and then stop by Sweet Paradise Chocolatier.
To see reviews, where to stay, maps, and tourist information, read Wailea sightseeing planner .
Traveling by combination of flight and bus from Kailua-Kona to Wailea takes 5.5 hours. Alternatively, you can do a combination of flight and car. In December, daytime highs in Wailea are 32°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 30th (Wed) early enough to drive to Kihei.
To see reviews, where to stay, maps, and tourist information, read Wailea sightseeing planner .
Traveling by combination of flight and bus from Kailua-Kona to Wailea takes 5.5 hours. Alternatively, you can do a combination of flight and car. In December, daytime highs in Wailea are 32°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 30th (Wed) early enough to drive to Kihei.
Things to do in Wailea
Side Trip
Maui
Highlights from your plan

Ahihi-Kinau Natural Area Reserve
11:30am, Tue Dec 29

Wailea Beach
10:00am, Wed Dec 30

Molokini Crater
2:30pm, Tue Dec 29
1
night
Kihei, Maui
1
night

Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.On the 31st (Thu), immerse yourself in nature at Iao Valley, observe the fascinating underwater world at Maui Ocean Center, and then relax in the rural setting at Surfing Goat Dairy.
To see maps, reviews, traveler tips, and tourist information, read our Kihei trip itinerary builder tool .
Kihei is just a stone's throw from Wailea. In December in Kihei, expect temperatures between 32°C during the day and 22°C at night. Wrap up your sightseeing on the 31st (Thu) early enough to travel back home.
Things to do in Kihei
Side Trips
Wailuku, Surfing Goat Dairy
Highlights from your plan

Maui Ocean Center
1:00pm, Thu Dec 31

Iao Valley
10:00am, Thu Dec 31

Surfing Goat Dairy
4:00pm, Thu Dec 31
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