14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Honolulu, Oahu
— 5 nights
Kailua-Kona, Island of Hawaii
— 2 nights
Hilo, Island of Hawaii
— 2 nights
Kihei, Maui
— 3 nights


Honolulu, Oahu

— 5 nights

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.
Visit Waikiki Beach and Sunset Beach Park for some beach relaxation. USS Arizona Memorial and Iolani Palace will appeal to museum buffs. Venture out of the city with trips to Haleiwa (Waimea Bay & Scuba & Snorkeling), Polynesian Cultural Center (in Laie) and Pu’u O Mahuka Heiau State Monument (in Pupukea). There's lots more to do: browse the different shops at Ala Moana Center, take in the pleasant sights at Diamond Head State Monument, take in the dramatic scenery at Manoa Falls, and identify plant and animal life at Hanauma Bay Nature Preserve.

To see other places to visit, maps, traveler tips, and tourist information, read our Honolulu driving holiday planner.

Sydney, Australia to Honolulu is an approximately 13.5-hour flight. The time zone difference when traveling from Sydney to Honolulu is minus 20 hours. Traveling from Sydney in July, expect Honolulu to be much warmer, temps between 36°C and 28°C. Finish your sightseeing early on the 11th (Sat) so you can travel to Kailua-Kona.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Kailua-Kona, Island of Hawaii

— 2 nights

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 12th (Sun): explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, then stop by Captain Cook Trading Co., and then get close to the beloved marine mammals with a swim-with-the-dolphins experience. Here are some ideas for day two: kick back and relax at Mauna Kea Beach and then admire the majestic nature at Hapuna Beach State Recreation Area.

To find ratings, where to stay, other places to visit, and tourist information, go to the Kailua-Kona trip itinerary site.

You can fly from Honolulu to Kailua-Kona in 4 hours. Expect a daytime high around 35°C in July, and nighttime lows around 28°C. Cap off your sightseeing on the 13th (Mon) early enough to go by car to Hilo.

Things to do in Kailua-Kona

Outdoors · Parks · Beaches · Nature

Side Trips

Hilo, Island of Hawaii

— 2 nights

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.
On the 14th (Tue), tour the pleasant surroundings at Kilauea Iki Trailhead, view the masterpieces at Volcano Art Center Gallery, then tour the pleasant surroundings at Devastation Trail, then take in nature's colorful creations at Liliuokalani Gardens, and finally admire the sheer force of Akaka Falls State Park. On the next day, browse the fresh offerings at Hilo Farmers Market.

To find other places to visit, traveler tips, maps, and tourist information, use the Hilo online trip itinerary planner.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. Expect a bit cooler evenings in Hilo when traveling from Kailua-Kona in July, with lows around 25°C. Wrap up your sightseeing by early afternoon on the 15th (Wed) to allow time for travel to Kihei.

Things to do in Hilo

Parks · Shopping · Outdoors · Trails

Side Trip

Kihei, Maui

— 3 nights
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.
You'll visit kid-friendly attractions like Wailea Beach and Maui Ocean Center. Escape the urban bustle at Haleakala Crater and Kalepolepo Beach Park. It doesn't end there: admire all the interesting features of Hana Highway - Road to Hana and admire the masterpieces at Art On Market.

For where to stay, photos, other places to visit, and tourist information, refer to the Kihei online trip maker.

You can fly from Hilo to Kihei in 3 hours. July in Kihei sees daily highs of 37°C and lows of 26°C at night. On the 18th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Kihei

Parks · Outdoors · Scenic Drive · Beaches

Side Trips

Hawaii travel guide

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.