14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii holiday maker

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

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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.
Venture out of the city with trips to Haleakala Crater (in Haleakala National Park), Lahaina (Lahaina Banyan Court, Scuba & Snorkeling, &more) and Zipline (in Kula). Spend the 22nd (Tue) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: admire the majestic nature at Iao Valley, stroll through Kalepolepo Beach Park, and observe the fascinating underwater world at Maui Ocean Center.

Plan trip to Kihei with our itinerary maker to find out where to go and what to do.

Chicago to Kihei is an approximately 13.5-hour flight. You'll gain 4 hours traveling from Chicago to Kihei due to the time zone difference. Expect much warmer temperatures when traveling from Chicago in December; daily highs in Kihei reach 82°F and lows reach 66°F. Wrap up your sightseeing on the 24th (Thu) early enough to travel to Hilo.

Things to do in Kihei

Outdoors · Parks · Scenic Drive

Side Trips

Lahaina, Wailuku, Hana Highway - Road to Hana, Haleakala Crater, Zipline
Highlights from your plan
Maui Escape Rooms ©
Maui Escape Rooms
Haleakala Crater ©
Haleakala Crater
Scuba & Snorkeling

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.
Explore Hilo's surroundings by going to Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Nature & Wildlife Tours, Kilauea Iki Trailhead, &more). There's lots more to do: take in the dramatic scenery at Akaka Falls State Park, kick your exploration up a notch at Umauma Falls Zipline & Rappel Experience, explore and take pictures at Banyan Drive, and take in nature's colorful creations at Liliuokalani Gardens.

To see where to stay, photos, and more tourist information, you can read our Hilo holiday planner.

Traveling by flight from Kihei to Hilo takes 3 hours. In December, daytime highs in Hilo are 80°F, while nighttime lows are 65°F. Cap off your sightseeing on the 27th (Sun) early enough to go by car to Kailua-Kona.

Things to do in Hilo

Outdoors · Parks · Tours

Side Trips

Hawaii Volcanoes National Park, Jagger Museum, Banyan Drive, Umauma Falls Zipline & Rappel Experience
Highlights from your plan
Umauma Falls Zipline & Rappel Experience ©
Umauma Falls Zipline & Rappel Experience
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Akaka Falls State Park ©
Akaka Falls State Park

1
night
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.
On the 28th (Mon), enjoy the sand and surf at Kahaluu Beach, get close to the beloved marine mammals with a swim-with-the-dolphins experience, and then kick your exploration up a notch at Hawaii Forest and Trail.

To see other places to visit, reviews, maps, and more tourist information, go to the Kailua-Kona itinerary planning website.

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In December, daily temperatures in Kailua-Kona can reach 82°F, while at night they dip to 70°F. Finish up your sightseeing early on the 28th (Mon) so you can travel to Honolulu.

Things to do in Kailua-Kona

Outdoors · Tours · Wildlife

Side Trip

Kahaluu Beach
Highlights from your plan
Swim with Dolphins
Hawaii Forest and Trail ©
Hawaii Forest and Trail
Kahaluu Beach ©
Kahaluu Beach

6
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), Pupukea (Ehukai Beach Park & Pu’u O Mahuka Heiau State Monument) and Kailua Beach Park (in Kailua). The adventure continues: stroll the grounds of USS Arizona Memorial, make a trip to Battleship Missouri Memorial, take in the pleasant sights at Diamond Head State Monument, and take in the dramatic scenery at Manoa Falls.

Plan my day in Honolulu using traveler tips and tourist information provided by Inspirock.

Traveling by flight from Kailua-Kona to Honolulu takes 4 hours. In December, daytime highs in Honolulu are 82°F, while nighttime lows are 69°F. Wrap up your sightseeing on the 3rd (Sun) early enough to travel back home.

Things to do in Honolulu

Parks · Outdoors · Beaches

Side Trips

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

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