14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock United States holiday planner

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Route & dates

14 days in Hawaii Itinerary

Start: Chicago
Fly:  11​h 30​min
1
Honolulu, Oahu
— 4 nights
Fly:  2​h 30​min
2
Kihei, Maui
— 3 nights
bus + Fly:  2​h 15​min
3
Kailua-Kona
— 2 nights
Drive:  2​h
4
Hilo
— 3 nights
Fly:  13​h
End: Chicago


Learn more about your trip

4
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.
Your day-by-day itinerary now includes Ala Moana Center. Step out of the city life by going to Lanikai Beach and Nuuanu Pali Lookout. Discover out-of-the-way places like National Memorial Cemetery of the Pacific and Byodo-In Temple. The adventure continues: pause for some photo ops at USS Arizona Memorial, see the vivid underwater world at Pele's Chair, and explore and take pictures at Diamond Head State Monument.

To see more things to do, reviews, ratings, and more tourist information, go to the Honolulu trip planner.

Chicago to Honolulu is an approximately 11.5-hour flight. You'll gain 4 hours traveling from Chicago to Honolulu due to the time zone difference. Traveling from Chicago in October, things will get much hotter in Honolulu: highs are around 87°F and lows about 74°F. Wrap up your sightseeing on the 14th (Mon) early enough to travel to Volcano.

Things to do in Honolulu

Parks Outdoors Trails

Side Trips

Oahu, Lanikai Beach, Byodo-In Temple
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Koko Crater Railway Trail ©
Koko Crater Railway Trail

3
nights
Kihei, Maui

Kihei ©
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.
Your day-by-day itinerary now includes Zipline as well as Maui Brewing Company. Explore hidden gems such as Parasailing & Paragliding and Ulua Beach. Escape the urban bustle at Kamaole Beach Park II and Ho'okipa Beach Park. Step out of Kihei to go to Lahaina and see Kai Pua Artist Studio, which is approximately 48 minutes away. There's still lots to do: enjoy the sand and surf at Kamaole Beach Park III and tour the pleasant surroundings at Makena Beach.

Plan a trip to Kihei easily and quickly by telling Inspirock to suggest an itinerary.

You can fly from Volcano to Kihei in 4.5 hours. Alternatively, you can do a combination of bus and flight. In October, daily temperatures in Kihei can reach 88°F, while at night they dip to 70°F. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow enough time to travel back home.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Ho'okipa Beach Park, Kai Pua Artist Studio, Zipline, Parasailing & Paragliding
Highlights from your plan
Kamaole Beach Park II ©
Kamaole Beach Park II
Zipline
Parasailing & Paragliding

2
nights
Kailua-Kona

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.
On the 17th (Thu), look for gifts at The Original Donkey Ball Store and then contemplate in the serene atmosphere at Mokuaikaua Church. Get ready for a full day of sightseeing on the 18th (Fri): enjoy the sand and surf at Kahaluu Beach, immerse yourself in nature at Kahalu'u Beach Park, and then enjoy the sand and surf at White Sand Beach.

To find photos, more things to do, maps, and other tourist information, use the Kailua-Kona trip planner .

You can fly from Kihei to Kailua-Kona in 2.5 hours. Other options are to do a combination of taxi and flight; or do a combination of flight and bus. Expect a daytime high around 86°F in October, and nighttime lows around 75°F. Wrap up your sightseeing on the 19th (Sat) early enough to drive to Hilo.

Things to do in Kailua-Kona

Parks Beaches Outdoors

Side Trips

Keauhou, Hapuna Beach State Recreation Area, The Original Donkey Ball Store
Highlights from your plan
Hapuna Beach State Recreation Area ©
Mokuaikaua Church ©
Mokuaikaua Church
Kahalu'u Beach Park ©
Kahalu'u Beach Park

3
nights
Hilo

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.
Start off your visit on the 20th (Sun): get to know the fascinating history of Basically Books, admire the natural beauty at Liliuokalani Gardens, then kick back and relax at Richardson Beach Park, and finally explore the striking landscape at Kapoho Tide Pools. Keep things going the next day: browse the fresh offerings at Hilo Farmers Market, then see some colorful creatures with a scuba or snorkeling tour, then stop by Big Island Candies, and finally stroll the grounds of Alae Cemetery.

To see reviews, photos, traveler tips, and more tourist information, read our Hilo route maker .

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in October, plan for little chillier nights in Hilo, with lows around 70°F. Wrap up your sightseeing by early afternoon on the 22nd (Tue) to allow time for travel back home.

Things to do in Hilo

Parks Outdoors Wildlife

Side Trips

Big Island Candies, Kapoho Tide Pools
Highlights from your plan
Liliuokalani Gardens ©
Liliuokalani Gardens
Richardson Beach Park ©
Richardson Beach Park
Kapoho Tide Pools ©
Kapoho Tide Pools

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