14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock United States holiday planner

Plan created by another user. Make it yours
1
Honolulu, Oahu
— 4 nights
2
Kihei, Maui
— 3 nights
3
Kailua-Kona
— 2 nights
4
Hilo
— 3 nights

S M T W T F S
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4
nights
Honolulu, Oahu

Honolulu ©

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.
Ala Moana Center has been added to your itinerary. Satisfy your inner culture vulture at USS Arizona Memorial and Byodo-In Temple. Explore hidden gems such as Koko Crater Railway Trail and Nu’uanu Pali. When in Honolulu, make a side trip to see Lanikai Beach in Kailua, approximately Kailua away. Next up on the itinerary: appreciate the extensive heritage of Makapuu Lighthouse Trail, hike along Diamond Head State Monument, see the vivid underwater world at Pele's Chair, and explore the different monuments and memorials at National Memorial Cemetery of the Pacific.

To see where to stay, maps, other places to visit, and other tourist information, read our Honolulu trip itinerary builder site.

Chicago to Honolulu is an approximately 12-hour flight. The time zone difference moving from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST) is minus 4 hours. Prepare for much warmer weather when traveling from Chicago in October: high temperatures in Honolulu hover around 87°F and lows are around 74°F. Finish up your sightseeing early on the 14th (Mon) so you can travel to Kihei.

Things to do in Honolulu

Parks · Outdoors · Trails · Historic Sites

Side Trips

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

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. Get outdoors at Parasailing & Paragliding and Ho'okipa Beach Park. Discover out-of-the-way places like Kamaole Beach Park II and Kai Pua Artist Studio. Next up on the itinerary: tour the pleasant surroundings at Ulua Beach and enjoy the sand and surf at Makena Beach.

To see maps, more things to do, where to stay, and other tourist information, refer to the Kihei route maker app.

Traveling by flight from Honolulu to Kihei takes 3 hours. In October, daytime highs in Kihei are 88°F, while nighttime lows are 70°F. Wrap up your sightseeing by early afternoon on the 17th (Thu) to allow time for travel to Kailua-Kona.

Things to do in Kihei

Outdoors · Parks · Beaches · Adventure

Side Trips

Highlights from your plan
Parasailing & Paragliding
Zipline
Kamaole Beach Park II ©
Kamaole Beach Park II

2
nights
Kailua-Kona

Kailua-Kona ©

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.
Kick off your visit on the 17th (Thu): look for gifts at The Original Donkey Ball Store and then take in the spiritual surroundings of Mokuaikaua Church. Keep things going the next day: enjoy the sand and surf at Kahaluu Beach, then admire the majestic nature at Kahalu'u Beach Park, and then kick back and relax at White Sand Beach.

To see other places to visit, where to stay, reviews, and more tourist information, use the Kailua-Kona itinerary site.

You can fly from Kihei to Kailua-Kona in 5.5 hours. 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 · Outdoors · Beaches · Nature

Side Trips

Highlights from your plan
Kahaluu Beach ©
Kahaluu Beach
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Kahalu'u Beach Park ©
Kahalu'u Beach Park

3
nights
Hilo

Hilo ©

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 20th (Sun): look for gifts at Basically Books, admire the natural beauty at Liliuokalani Gardens, then enjoy the sand and surf at Richardson Beach Park, and finally take in the dramatic natural features at Kapoho Tide Pools. Get ready for a full day of sightseeing on the next day: pick up some local products at Hilo Farmers Market, then identify plant and animal life at Wildlife Areas, then look for gifts at Big Island Candies, and finally explore the different monuments and memorials at Alae Cemetery.

To see other places to visit, ratings, maps, and tourist information, you can read our Hilo itinerary app.

You can drive from Kailua-Kona to Hilo in 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 enough time to travel back home.

Things to do in Hilo

Parks · Outdoors · Wildlife · Shopping

Side Trips

Highlights from your plan
Liliuokalani Gardens ©
Liliuokalani Gardens
Richardson Beach Park ©
Richardson Beach Park
Kapoho Tide Pools ©
Kapoho Tide Pools

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