14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii route planner

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

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4
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.
Get out of town with these interesting Kihei side-trips: Ho'okipa Beach Park (in Paia), Lahaina (Lahaina Banyan Court & Ka'anapali Beach) and Haleakala Crater (in Haleakala National Park). There's lots more to do: take a memorable drive along Hana Highway - Road to Hana, relax in the rural setting at Maui Tropical Plantation, admire the majestic nature at Iao Valley, and tour the pleasant surroundings at Kalepolepo Beach Park.

To see more things to do, where to stay, ratings, and more tourist information, use the Kihei trip itinerary planning tool.

Newark to Kihei is an approximately 14-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Newark to Kihei. Prepare for a bit warmer weather when traveling from Newark in October: high temperatures in Kihei hover around 88°F and lows are around 70°F. Wrap up your sightseeing on the 12th (Sat) early enough to travel to Hilo.

Things to do in Kihei

Parks · Outdoors · Beaches · Nature

Side Trips

2
nights
Hilo, Island of Hawaii

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 13th (Sun): admire the sheer force of Akaka Falls State Park, then admire the natural beauty at Liliuokalani Gardens, then tour the pleasant surroundings at Kilauea Iki Trailhead, and finally trek along Kipuka Puaulu (Bird Park) Trail. On the 14th (Mon), you'll have a packed day of sightseeing: admire the sheer force of Rainbow Falls, get outside with Keanakakoi Crater Overlook, and then contemplate the geological forces at Kīlauea.

For more things to do, maps, ratings, and more tourist information, you can read our Hilo trip planner.

Getting from Kihei to Hilo by flight takes about 3 hours. In October, plan for daily highs up to 84°F, and evening lows to 70°F. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Nature · Trails

Side Trip

2
nights
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.
Start off your visit on the 15th (Tue): examine the collection at Kona Historical Society, explore the striking landscape of Pu'uhonua O Honaunau National Historical Park, then get engrossed in the history at Kona Coffee Living History Farm, and finally get interesting insight from Tours. On the 16th (Wed), you'll have a packed day of sightseeing: kick back and relax at Mauna Kea Beach and then kick back and relax at Hapuna Beach State Recreation Area.

For maps, other places to visit, where to stay, and other tourist information, go to the Kailua-Kona trip planning app.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In October, daily temperatures in Kailua-Kona can reach 86°F, while at night they dip to 75°F. Finish your sightseeing early on the 16th (Wed) so you can travel to Honolulu.

Things to do in Kailua-Kona

Outdoors · Parks · Beaches · Nature

Side Trips

5
nights
Honolulu, Oahu

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.
Explore the numerous day-trip ideas around Honolulu: Kailua Beach Park (in Kailua), Haleiwa (Sunset Beach Park & Waimea Bay) and Pu’u O Mahuka Heiau State Monument (in Pupukea). There's still lots to do: get engrossed in the history at USS Arizona Memorial, examine the collection at USS Bowfin Submarine Museum & Park, steep yourself in history at Battleship Missouri Memorial, and explore the activities along Hanauma Bay Nature Preserve.

To see more things to do, where to stay, photos, and other tourist information, you can read our Honolulu itinerary tool.

Getting from Kailua-Kona to Honolulu by flight takes about 4 hours. Expect a daytime high around 87°F in October, and nighttime lows around 74°F. Wrap up your sightseeing on the 21st (Mon) early enough to travel back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Nature

Side Trips

Hawaii travel guide

4.3
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.