40 days in Hawaii Itinerary

40 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder
Make it your trip
1
Honolulu, Oahu
— 10 nights
Fly
2
Lihue, Kauai
— 2 nights
Drive
3
Koloa, Kauai
— 2 nights
Drive
4
Haena, Kauai
— 1 day
Drive
5
Hanalei, Kauai
— 2 nights
Fly
6
Kailua-Kona, Island of Hawaii
— 5 nights
Drive
7
Honomu, Island of Hawaii
— 2 nights
Drive
8
Hilo, Island of Hawaii
— 2 nights
Drive
9
Pahoa, Island of Hawaii
— 2 nights
Drive
10
Hawaii Volcanoes National Park, Island of Hawaii
— 1 day
Drive
11
Volcano, Island of Hawaii
Fly to Hoolehua, Taxi to Molokai
12
Molokai
— 2 nights
Unknown
13
Lanai City, Lanai
— 1 night
Unknown
14
Kihei, Maui
— 9 nights
Drive

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Honolulu, Oahu — 10 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.
Get a sense of the local culture at Makapuu Lighthouse Trail and Honolulu Museum of Art. Give yourself a bit of retail therapy at Ala Moana Center and Moni Honolulu. You'll find plenty of places to visit near Honolulu: Pupukea (Banzai Pipeline & Shark's Cove), Waimanalo (Bellows Field Beach Park & Waimanalo Beach) and Haleiwa (Waimea Valley, Waimea Bay, &more). There's still lots to do: work some fitness into your day at Ala Moana Beach Park, examine the collection at Pearl Harbor Aviation Museum, get close to the beloved marine mammals with Dolphin Quest, and stroll around Magic Island.

For more things to do, photos, and other tourist information, use the Honolulu itinerary site.

Use the Route module to find travel options from your starting location to Honolulu. In August in Honolulu, expect temperatures between 88°F during the day and 75°F at night. Cap off your sightseeing on the 4th (Sun) early enough to catch the flight to Lihue.
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Find places to stay Aug 25 — Sep 4:

Lihue, Kauai — 2 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Get ready for a full day of sightseeing on the next day: Head underground at Wet and Dry Caves, Kauai, enjoy the sand and surf at Donkey Beach, then kick back and relax at Kealia Beach, and finally take in the dramatic scenery at Secret Falls (Uluwehi Falls).

For ratings, maps, reviews, and more tourist information, go to the Lihue day trip planning website.

You can fly from Honolulu to Lihue in 2.5 hours. In September in Lihue, expect temperatures between 86°F during the day and 76°F at night. Finish your sightseeing early on the 6th (Tue) to allow enough time to drive to Koloa.
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Find places to stay Sep 4 — 6:

Koloa, Kauai — 2 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Kick off your visit on the 7th (Wed): kick back and relax at Baby Beach, then tour the pleasant surroundings at Lawa'i Beach, and then wander the streets of Old Koloa Town.

For reviews, maps, where to stay, and more tourist information, refer to the Koloa trip itinerary planner.

Koloa is very close to Lihue. Expect a daytime high around 86°F in September, and nighttime lows around 76°F. Wrap up your sightseeing on the 8th (Thu) early enough to drive to Haena.
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Find places to stay Sep 6 — 8:

Haena, Kauai — 1 day

Hāena State Park is a state park located on the north shore of the Hawaiian island of Kauai. Kick off your visit on the 8th (Thu): admire the majestic nature at Hāʻena State Park, then tour the pleasant surroundings at Ke'e Beach, and then trek along Hanakapi`ai Trail.

To see maps, other places to visit, where to stay, and other tourist information, read our Haena planning tool.

You can drive from Koloa to Haena in 2 hours. Finish up your sightseeing early on the 8th (Thu) so you can go by car to Hanalei.
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Find places to stay Sep 8 — 9:

Hanalei, Kauai — 2 nights

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Start off your visit on the 9th (Fri): trek along Okolehao Trail, look for all kinds of wild species at Hanalei National Wildlife Refuge, enjoy the sand and surf at Pali Ke Kua Beach (Hideaway s Beach), see some colorful creatures with a scuba or snorkeling tour, then admire the sheer force of Hanakoa Falls, and finally admire the majestic nature at Koke`e State Park.

To see maps, more things to do, other places to visit, and other tourist information, you can read our Hanalei holiday planning app.

Hanalei is just a short distance from Haena. In September in Hanalei, expect temperatures between 86°F during the day and 76°F at night. Finish your sightseeing early on the 10th (Sat) so you can fly to Kailua-Kona.
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Find places to stay Sep 8 — 10:

Kailua-Kona, Island of Hawaii — 5 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.
Escape the urban bustle at Hapuna Beach State Recreation Area and Kealakekua Bay. You'll explore the less-touristy side of things at Manini'owali Beach (Kua Bay) and Magic Sands. Venture out of the city with trips to Scuba & Snorkeling (in Kealakekua) and 49 Black Sand Beach (in Waikoloa). And it doesn't end there: enjoy the sand and surf at White Sand Beach, immerse yourself in nature at Kahalu'u Beach Park, contemplate the waterfront views at Kiholo Bay, and stroll through Makalawena/Pu'u Ali'i.

To find traveler tips and more tourist information, refer to the Kailua-Kona sightseeing planner.

Getting from Hanalei to Kailua-Kona by flight takes about 2.5 hours. In September in Kailua-Kona, expect temperatures between 87°F during the day and 76°F at night. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Honomu.
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Find places to stay Sep 10 — 15:

Honomu, Island of Hawaii — 2 nights

Honomū is a census-designated place (CDP) in Hawai‘i County, Hawai‘i, United States. Kick off your visit on the 15th (Thu): see the interesting displays at Hawaii Plantation Museum, take in the dramatic scenery at Umauma Falls, then tour the pleasant surroundings at Laupahoehoe Beach Park, and finally admire the majestic nature at Kalopa State Recreation Area. Keep things going the next day: kick back and relax at Kolekole Beach Park, enjoy the sand and surf at Onomea Bay, and then experience rural life at Onomea Tea Company.

To see other places to visit, ratings, where to stay, and other tourist information, use the Honomu trip itinerary maker tool.

Getting from Kailua-Kona to Honomu by car takes about 2 hours. Traveling from Kailua-Kona in September, Honomu is a bit cooler at night with lows of 71°F. Cap off your sightseeing on the 17th (Sat) early enough to go by car to Hilo.
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Find places to stay Sep 15 — 17:

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.
Kick off your visit on the 17th (Sat): take in the dramatic scenery at Rainbow Falls, hike along Native Hawaiian Lava, get impressive views of Pu'u 'O'o Vent, enjoy the sand and surf at Richardson Beach Park, then tour the pleasant surroundings at Carlsmith Beach Park, and finally take in nature's colorful creations at Liliuokalani Gardens. Here are some ideas for day two: admire the sheer force of Akaka Falls State Park, see the interesting displays at Pacific Tsunami Museum, make a trip to Pepeekeo Scenic Drive, take in nature's colorful creations at Hawaii Tropical Bioreserve and Garden, then take in the dramatic natural features at Boiling Pots, and finally hike along Pu'u 'O'o Trail.

Find out how to plan Hilo trip without stress by asking Inspirock to help create an itinerary.

Hilo is very close to Honomu. In September, plan for daily highs up to 86°F, and evening lows to 71°F. Wrap up your sightseeing on the 19th (Mon) early enough to drive to Pahoa.
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Side Trip
Find places to stay Sep 17 — 19:

Pahoa, Island of Hawaii — 2 nights

Pāhoa is a census-designated place (CDP) in Hawai‘i County, Hawai‘i, United States located in the District of Puna. Start off your visit on the 19th (Mon): contemplate in the serene atmosphere at Star of the Sea Painted Church, browse the eclectic array of goods at Uncle Robert's Awa Bar and Farmers Market, and then kick back and relax at Kaimu Beach Park. Here are some ideas for day two: admire the majestic nature at MacKenzie State Park, then make a trip to Red Road (Hwy 137), and then have fun at Pahoa Pool.

To see reviews, ratings, more things to do, and more tourist information, you can read our Pahoa trip planner.

You can drive from Hilo to Pahoa in an hour. Another option is to take a bus. September in Pahoa sees daily highs of 86°F and lows of 71°F at night. Cap off your sightseeing on the 21st (Wed) early enough to travel to Hawaii Volcanoes National Park.
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Find places to stay Sep 19 — 21:

Hawaii Volcanoes National Park, Island of Hawaii — 1 day

Volcanoes have played an important role in shaping the Earth, and Hawaii Volcanoes National Park shows visitors the process in action.
Start off your visit on the 21st (Wed): take a memorable drive along Devastation Trail, then stroll through Sulphur Banks, then tour the pleasant surroundings at Kipuka Puaulu (Bird Park) Trail, and finally trek along Napau-Makaopuhi Crater Trail.

To see maps, ratings, photos, and other tourist information, go to the Hawaii Volcanoes National Park sightseeing planner.

Traveling by car from Pahoa to Hawaii Volcanoes National Park takes 1.5 hours. In September, daily temperatures in Hawaii Volcanoes National Park can reach 86°F, while at night they dip to 71°F. Finish up your sightseeing early on the 21st (Wed) so you can travel to Volcano.
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Outdoors · Parks · Trails · Wildlife
Find places to stay Sep 21 — 22:

Volcano, Island of Hawaii

Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
To see ratings, more things to do, traveler tips, and other tourist information, refer to the Volcano road trip planning website.

Volcano is very close to Hawaii Volcanoes National Park. In September, daytime highs in Volcano are 86°F, while nighttime lows are 71°F. You'll set off for Molokai on the 21st (Wed).
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Find places to stay Sep 21 — 22:

Molokai — 2 nights

The Friendly Isle

Start off your visit on the 22nd (Thu): enjoy the sand and surf at Kapukahehu Beach, then enjoy the sand and surf at Kawakiu Beach, and then tour the pleasant surroundings at Waialua Beach. Get ready for a full day of sightseeing on the 23rd (Fri): look for all kinds of wild species at Kamakou Preserve, admire the sheer force of Halawa Falls, and then see the vivid underwater world at Barrier Reef.

To find maps, other places to visit, reviews, and tourist information, use the Molokai online vacation planner.

Traveling by combination of flight and taxi from Volcano to Molokai takes 4 hours. September in Molokai sees daily highs of 85°F and lows of 73°F at night. Cap off your sightseeing on the 23rd (Fri) early enough to travel to Lanai City.
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Find places to stay Sep 21 — 23:

Lanai City, Lanai — 1 night

Lanai City is a census-designated place (CDP) on the island of Lanai, in Maui County, Hawaii, United States. To find where to stay, maps, and other tourist information, go to the Lanai City trip tool.

The Route module can help you plan travel from Molokai to Lanai City. Traveling from Molokai in September, Lanai City is little chillier at night with lows of 68°F. You'll set off for Kihei on the 24th (Sat).
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Find places to stay Sep 23 — 24:

Kihei, Maui — 9 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.
Escape the urban bustle at Kapalua Coastal Trail and Kapalua Beach. Step off the beaten path and head to Honolua Bay and Makena Beach. Venture out of the city with trips to D.T. Fleming Park (in Kapalua) and Lahaina (Kahekili Beach Park, Off-Road Tours, &more). Next up on the itinerary: kick back and relax at Ulua Beach, tour the pleasant surroundings at Wailea Beach Path, stroll around Cove Park, and see majestic marine mammals with Maui Kayaks.

To find ratings, where to stay, other places to visit, and other tourist information, refer to the Kihei trip planner.

Use the Route module to find suitable travel options from Lanai City to Kihei. Traveling from Lanai City in September, you will find days in Kihei are a bit warmer (90°F), and nights are about the same (72°F). Wrap up your sightseeing on the 3rd (Mon) early enough to drive back home.
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Find places to stay Sep 24 — Oct 3:

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.
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