37 days in Hawaii Itinerary

37 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner
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Fly
1
Honolulu, Oahu
— 9 nights
Drive
2
Haleiwa, Oahu
— 2 nights
Fly
3
Koloa, Kauai
— 5 nights
Fly
4
Lahaina, Maui
— 8 nights
Fly
5
Hilo, Island of Hawaii
— 5 nights
Drive
6
Kailua-Kona, Island of Hawaii
— 7 nights
Fly

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Honolulu, Oahu — 9 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.
We've included these beaches for you: Waikiki Beach and Kailua Beach Park. Step out of the city life by going to Diamond Head State Monument and Hanauma Bay Nature Preserve. Venture out of the city with trips to Makapu'u Beach (in Waimanalo), Kapolei (Ihilani Spa & Rainbow Reef) and Lanikai Beach (in Kailua). There's still lots to do: discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Kapiolani Regional Park, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, and step aboard Battleship Missouri Memorial.

To see other places to visit, ratings, where to stay, and more tourist information, use the Honolulu travel itinerary planner.

Austin to Honolulu is an approximately 9-hour flight. The time zone changes from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST), which is usually a -4 hour difference. Traveling from Austin in October, expect somewhat warmer with lows of 74°F in Honolulu. Wrap up your sightseeing on the 10th (Mon) to allow time to drive to Haleiwa.
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Parks · Outdoors · Beaches · Wildlife
Side Trips
Find places to stay Oct 1 — 10:

Haleiwa, Oahu — 2 nights

Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. Your day by day itinerary now includes Banzai Divers Hawaii as well as The Surf Bus. On the 11th (Tue), have unforgettable encounters with Banzai Divers Hawaii, see The Surf Bus, pause for some photo ops at Pu’u O Mahuka Heiau State Monument, kick back and relax at Turtle Bay Beach, then tour the pleasant surroundings at Sunset Beach Park, and finally enjoy the sand and surf at Shark's Cove. Here are some ideas for day two: discover the deep blue sea with Bob Marlin Charters, then kick back and relax at Haleiwa Beach Park, and then kick back and relax at Laniakea Beach.

For reviews, maps, photos, and more tourist information, use the Haleiwa road trip tool.

You can drive from Honolulu to Haleiwa in an hour. Alternatively, you can take a bus. Traveling from Honolulu in October, expect Haleiwa to be a bit cooler, temps between 81°F and 68°F. Cap off your sightseeing on the 12th (Wed) early enough to catch the flight to Koloa.
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Outdoors · Beaches · Parks · Wildlife
Side Trips
Find places to stay Oct 10 — 12:

Koloa, Kauai — 5 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. You'll get in some beach time at Poipu Beach Park and Anini Beach. Take a break from the city and head to Na Pali Coast State Park and Waimea Canyon State Park. Explore Koloa's surroundings by going to Puu Hinahina Lookout (in Waimea), Hanalei Valley Lookout (in Princeville) and Hanalei (Michal - Art Studio & Boutique of Hanalei & Hanalei Beach). And it doesn't end there: get a dose of the wild on Kauai Safaris, enjoy the sand and surf at Lawa'i Beach, take in the dramatic scenery at Opaekaa Falls, and stroll through Kalapaki Beach.

To see traveler tips, where to stay, more things to do, and tourist information, you can read our Koloa day trip app.

Getting from Haleiwa to Koloa by flight takes about 2.5 hours. Expect a bit warmer evenings in Koloa when traveling from Haleiwa in October, with lows around 74°F. Finish up your sightseeing early on the 17th (Mon) so you can catch the flight to Lahaina.
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Outdoors · Parks · Beaches · Nature
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Find places to stay Oct 12 — 17:

Lahaina, Maui — 8 nights

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.
Visit Ka'anapali Beach and D.T. Fleming Park for some beach relaxation. Get outdoors at Scuba & Snorkeling and Kapalua Beach. Change things up with these side-trips from Lahaina: Iao Valley (in Wailuku), Story of Hawaii Museum (in Kahului) and Wailea (Wailea Beach, Maluaka Beach, &more). Spend the 20th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: get impressive views of Haleakala Crater, take a stroll through Lahaina Front Street, enjoy the sand and surf at Slaughterhouse Beach, and stroll through Napili Beach.

To see other places to visit, where to stay, reviews, and other tourist information, go to the Lahaina day trip planning website.

Getting from Koloa to Lahaina by flight takes about 2.5 hours. October in Lahaina sees daily highs of 84°F and lows of 73°F at night. Finish your sightseeing early on the 25th (Tue) so you can fly to Hilo.
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Outdoors · Parks · Beaches · Scenic Drive
Side Trips
Find places to stay Oct 17 — 25:

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.
Visit Richardson Beach Park and Onomea Bay for some beach relaxation. Step out of the city life by going to Akaka Falls State Park and Kipuka Puaulu (Bird Park) Trail. Change things up with these side-trips from Hilo: Hawaii Volcanoes National Park (Kīlauea, Nature & Wildlife Tours, &more), Steam Vents (in Pahoa) and Punalu‘U Beach (in Pahala). The adventure continues: admire the natural beauty at Liliuokalani Gardens, look for all kinds of wild species at Hawaii Tropical Bioreserve and Garden, explore the different monuments and memorials at Alae Cemetery, and tour the pleasant surroundings at Keaukaha Beach Park.

To see traveler tips, other places to visit, reviews, and other tourist information, read our Hilo online tour planner.

You can fly from Lahaina to Hilo in 2.5 hours. In October in Hilo, expect temperatures between 84°F during the day and 70°F at night. Wrap up your sightseeing on the 30th (Sun) early enough to drive to Kailua-Kona.
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Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Oct 25 — 30:

Kailua-Kona, Island of Hawaii — 7 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.
Get outdoors at Swim with Dolphins and Pu'uhonua O Honaunau National Historical Park. Visit Hapuna Beach State Recreation Area and Papakōlea Green Sand Beach for some beach relaxation. Explore the numerous day-trip ideas around Kailua-Kona: Anaehoomalu (in Waikoloa), The 1871 Trail (in Honaunau) and Puukohola National Historic Park (in Kawaihae). The adventure continues: look for all kinds of wild species at Kona Cloud Forest, take a memorable tour with Tours, enjoy the sand and surf at Waialea Beach, and stroll through Manini'owali Beach (Kua Bay).

Plan trip to Kailua-Kona with our itinerary maker to find out where to go and what to do.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 86°F, and evening lows to 75°F. Wrap up your sightseeing on the 6th (Sun) early enough to fly back home.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Oct 30 — Nov 6:

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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