14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route planner

Plan created by another user. Make it yours
1
Kailua-Kona, Island of Hawaii
— 1 night
2
Hilo, Island of Hawaii
— 1 night
3
Lahaina, Maui
— 4 nights
4
Lihue, Kauai
— 1 night
5
Honolulu, Oahu
— 6 nights

S M T W T F S
18
19
20
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22
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24
25
26
27
28
29
30
31

1
night
Kailua-Kona, Island of Hawaii

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 18th (Sun), contemplate the long history of Puukohola National Historic Park and then kick back and relax at Mauna Kea Beach. On the next day, browse the exhibits of Kona Coffee Living History Farm, explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, then get engrossed in the history at H.N. Greenwell Store Museum, then get close to the beloved marine mammals with a swim-with-the-dolphins experience, and finally take in the spiritual surroundings of Mokuaikaua Church.

To find other places to visit, maps, traveler tips, and other tourist information, refer to the Kailua-Kona sightseeing planner.

Pittsburgh to Kailua-Kona is an approximately 13.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Pittsburgh to Kailua-Kona. Plan for much hotter temperatures traveling from Pittsburgh in October, with highs in Kailua-Kona at 86°F and lows at 75°F. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Outdoors · Parks · Wildlife · Tours

Side Trips

Highlights from your plan
Swim with Dolphins
Pu'uhonua O Honaunau National Historical Park ©
Mauna Kea Beach ©
Mauna Kea Beach

1
night
Hilo, Island of Hawaii

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.
Kick off your visit on the 20th (Tue): admire the natural beauty at Liliuokalani Gardens, get a new perspective on nature at Mokupapapa Discovery Center, then admire the majestic nature at Akaka Falls State Park, and finally get interesting insight from Umauma Falls Zipline & Rappel Experience.

To find photos, traveler tips, ratings, and more tourist information, use the Hilo online trip itinerary builder.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Expect slightly colder evenings in Hilo when traveling from Kailua-Kona in October, with lows around 70°F. Wrap up your sightseeing on the 20th (Tue) early enough to travel to Lahaina.

Things to do in Hilo

Parks · Outdoors · Adventure · Tours

Side Trip

Highlights from your plan
Umauma Falls Zipline & Rappel Experience ©
Umauma Falls Zipline & Rappel Experience
Liliuokalani Gardens ©
Liliuokalani Gardens
Akaka Falls State Park ©
Akaka Falls State Park

4
nights
Lahaina, Maui

Lahaina ©

Crown Jewel of 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.
Change things up with these side-trips from Lahaina: Kalepolepo Beach Park (in Kihei), Haleakala Crater (in Haleakala National Park) and Maui Pineapple Tours (in Makawao). Spend the 22nd (Thu) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: take a tour by water with Boat Tours & Water Sports, kick back and relax at Ka'anapali Beach, stroll around Lahaina Banyan Court, and test your problem-solving skills at Maui Escape Rooms.

To see where to stay, maps, reviews, and more tourist information, you can read our Lahaina trip itinerary builder.

You can fly from Hilo to Lahaina in 3.5 hours. Expect a daytime high around 84°F in October, and nighttime lows around 73°F. Cap off your sightseeing on the 24th (Sat) early enough to travel to Lihue.

Things to do in Lahaina

Parks · Outdoors · Scenic Drive · Nature

Side Trips

Highlights from your plan
Maui Escape Rooms ©
Maui Escape Rooms
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

1
night
Lihue, Kauai

Lihue ©
Lihue or LÄ«hue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. On the 25th (Sun), see Kipu Ranch Adventures, then kick your exploration up a notch at some of the top local zipline courses and adventure parks, and then take an unforgettable tour with a helicopter tour.

For reviews and tourist information, read our Lihue trip planner.

Traveling by flight from Lahaina to Lihue takes 3.5 hours. Expect a daytime high around 84°F in October, and nighttime lows around 74°F. Wrap up your sightseeing on the 25th (Sun) early enough to travel to Honolulu.

Things to do in Lihue

Tours · Outdoors · Adventure
Highlights from your plan
Kipu Ranch Adventures ©
Kipu Ranch Adventures
Zipline
Helicopter Tours

6
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.
When in Honolulu, make a side trip to see Kailua Beach Park in Kailua, approximately Kailua away. Next up on the itinerary: appreciate the history behind USS Arizona Memorial, see the interesting displays at USS Bowfin Submarine Museum & Park, stroll the grounds of National Memorial Cemetery of the Pacific, and admire the sheer force of Manoa Falls.

To see other places to visit, maps, more things to do, and tourist information, go to the Honolulu attractions planning tool.

You can fly from Lihue to Honolulu in 2.5 hours. In October, plan for daily highs up to 87°F, and evening lows to 74°F. Finish up your sightseeing early on the 31st (Sat) so you can travel back home.

Things to do in Honolulu

Side Trips

Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

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