37 days in Hawaii Itinerary

37 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner

Make it your trip
Fly
1
Kihei, Maui
— 8 nights
Fly
2
Hilo, Island of Hawaii
— 5 nights
Drive
3
Kailua-Kona, Island of Hawaii
— 6 nights
Fly
4
Lihue, Kauai
— 6 nights
Fly
5
Honolulu, Oahu
— 11 nights
Fly

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Kihei, Maui

— 8 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.
Venture out of the city with trips to Lahaina (Lahaina Banyan Court, Scuba & Snorkeling, &more), Zipline (in Ka'anapali) and Haleakala National Park (Sliding Sands Trail & Haleakala Crater). Spend the 21st (Tue) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: get up close and personal with brilliant marine life at Maui Ocean Center, kick back and relax at Kapalua Beach, stroll through Keawakapu Beach, and relax in the rural setting at Surfing Goat Dairy.

For photos, where to stay, and tourist information, go to the Kihei holiday planning site.

Sydney, Australia to Kihei is an approximately 15-hour flight. Traveling from Sydney to Kihei, you'll gain 20 hours due to the time zone difference. Plan for a bit warmer temperatures traveling from Sydney in September, with highs in Kihei at 38°C and lows at 26°C. Cap off your sightseeing on the 21st (Tue) early enough to catch the flight to Hilo.

Things to do in Kihei

Outdoors · Parks · Beaches · Scenic Drive

Side Trips

Hilo, Island of Hawaii

— 5 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.
Get out of town with these interesting Hilo side-trips: Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Volcano Art Center Gallery, Kilauea Iki Trailhead, &more). Next up on the itinerary: take in nature's colorful creations at Liliuokalani Gardens, browse the fresh offerings at Hilo Farmers Market, admire the sheer force of Akaka Falls State Park, and tour the pleasant surroundings at Hawaii Tropical Bioreserve and Garden.

To see maps, ratings, other places to visit, and more tourist information, refer to the Hilo day trip site.

You can fly from Kihei to Hilo in 2.5 hours. In September, daily temperatures in Hilo can reach 35°C, while at night they dip to 25°C. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Trails · Nature

Side Trips

Kailua-Kona, Island of Hawaii

— 6 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.
Explore the numerous day-trip ideas around Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau), Hapuna Beach State Recreation Area (in Puako) and Kula Kai Caverns (in Ocean View). And it doesn't end there: fulfill a lifelong dream with a swim-with-the-dolphins experience, enjoy the sand and surf at Kahaluu Beach, contemplate in the serene atmosphere at Mokuaikaua Church, and appreciate the views at Pololu Valley Lookout.

To see more things to do, other places to visit, photos, and tourist information, you can read our Kailua-Kona trip itinerary planner.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. September in Kailua-Kona sees daily highs of 36°C and lows of 28°C at night. Finish your sightseeing early on the 2nd (Sat) to allow enough time to fly to Lihue.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Beaches

Side Trips

Lihue, Kauai

— 6 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll find plenty of places to visit near Lihue: Waimea Canyon State Park (in Waimea), Swinging Bridge (in Hanapepe) and Na Pali Coast State Park (in Wainiha). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, tour the pleasant surroundings at Tunnels Beach, admire the sheer force of Hanakapiai Falls, and take in the dramatic natural features at Spouting Horn.

To find more things to do, traveler tips, photos, and tourist information, you can read our Lihue online travel route planner.

Fly from Kailua-Kona to Lihue in 2.5 hours. October in Lihue sees daily highs of 34°C and lows of 27°C at night. Finish your sightseeing early on the 8th (Fri) so you can fly to Honolulu.

Things to do in Lihue

Parks · Outdoors · Nature · Beaches

Side Trips

Honolulu, Oahu

— 11 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.
Explore Honolulu's surroundings by going to Kailua (Kailua Beach Park & Lanikai Beach), Pupukea (Ehukai Beach Park & Pu’u O Mahuka Heiau State Monument) and Haleiwa (Sunset Beach Park, Waimea Bay, &more). The adventure continues: stroll the grounds of USS Arizona Memorial, enjoy the sand and surf at Waikiki Beach, hit the best photo ops around with an inspiring photography tour, and make a trip to Battleship Missouri Memorial.

To see photos, reviews, traveler tips, and tourist information, refer to the Honolulu trip itinerary planner.

You can fly from Lihue to Honolulu in 2.5 hours. In October, plan for daily highs up to 36°C, and evening lows to 27°C. Wrap up your sightseeing by early afternoon on the 19th (Tue) to allow time for the flight back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Hawaii travel guide

4.4
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.