31 days in Hawaii Itinerary

31 days in Hawaii Itinerary

Created using Inspirock Hawaii attractions planner
Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 3 nights
Drive
2
Hilo, Island of Hawaii
— 4 nights
Fly
3
Kihei, Maui
— 8 nights
Fly
4
Koloa, Kauai
— 5 nights
Fly
5
Honolulu, Oahu
— 10 nights
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Kailua-Kona, Island of Hawaii — 3 nights

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.
Attractions like Swim with Dolphins and Pu'uhonua O Honaunau National Historical Park make great kid-friendly stops. Your itinerary includes some good beach time at Papakōlea Green Sand Beach and Kahaluu Beach. You'll find plenty of places to visit near Kailua-Kona: Naalehu (South Point Complex & Ka Lae Light), Honaunau Bay (in Honaunau) and Big Island Bees (in Captain Cook). The adventure continues: kick back and relax at Hapuna Beach State Recreation Area, get engrossed in the history at H.N. Greenwell Store Museum, stop by Kailua Pier, and look for all kinds of wild species at Kona Cloud Forest.

To see more things to do, reviews, traveler tips, and tourist information, refer to the Kailua-Kona trip itinerary website.

Orlando to Kailua-Kona is an approximately 14-hour flight. The time zone difference when traveling from Orlando to Kailua-Kona is minus 5 hours. When traveling from Orlando in July, plan for little chillier days and about the same nights in Kailua-Kona: temperatures range from 86°F by day to 76°F at night. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Hilo.
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Parks · Outdoors · Beaches · Wildlife
Side Trips

Hilo, Island of Hawaii — 4 nights

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.
You'll get in some beach time at Laupahoehoe Beach Park and Punalu‘U Beach. Attractions like Akaka Falls State Park and Rainbow Falls make great kid-friendly stops. You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Kalapana, Pu'u Loa Petroglyphs, &more). And it doesn't end there: look and learn at Imiloa Astronomy Center, look for gifts at Hilo Coffee Mill, take in nature's colorful creations at Liliuokalani Gardens, and take an unforgettable tour with a helicopter tour.

To see more things to do, maps, traveler tips, and other tourist information, read our Hilo trip planner.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Expect a bit cooler evenings in Hilo when traveling from Kailua-Kona in July, with lows around 71°F. Wrap up your sightseeing on the 8th (Fri) to allow time to fly to Kihei.
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Parks · Outdoors · Museums · Trails
Side Trips

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.
Your itinerary includes some good beach time at Wailea Beach and Kapalua Beach. Attractions like Maui Ocean Center and Ka'anapali Beach make great kid-friendly stops. Explore Kihei's surroundings by going to Haleakala National Park (Sliding Sands Trail & Haleakala Crater), Lahaina (Slaughterhouse Beach, Napili Beach, &more) and Kapalua (D.T. Fleming Park & Kapalua Resort). Spend the 16th (Sat) exploring the striking scenery along Hana Highway - Road to Hana. There's lots more to do: enjoy the sand and surf at Makena Beach, get outside with Outdoor Activities, stroll through Oneloa Beach, and immerse yourself in nature at Iao Valley.

To find where to stay, ratings, photos, and other tourist information, refer to the Kihei tour itinerary builder tool.

Traveling by flight from Hilo to Kihei takes 2.5 hours. In July, plan for daily highs up to 89°F, and evening lows to 72°F. Finish up your sightseeing early on the 16th (Sat) so you can catch the flight to Koloa.
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Outdoors · Parks · Beaches · Scenic Drive
Side Trips

Koloa, Kauai — 5 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Your itinerary includes some good beach time at Poipu Beach Park and Anini Beach. Family-friendly places like Tunnels Beach and Hanalei Beach will thrill your kids. Explore the numerous day-trip ideas around Koloa: Kauai Path (in Kapaa), Puu Poa Beach (in Princeville) and Kekaha (Boat Tours & Water Sports & Na Pali Makai). There's lots more to do: kick back and relax at Shipwreck Beach, stroll through Salt Pond Beach Park, immerse yourself in nature at Waimea Canyon State Park, and take in the dramatic natural features at Spouting Horn.

For photos, more things to do, traveler tips, and other tourist information, refer to the Koloa trip itinerary planning app.

Traveling by flight from Kihei to Koloa takes 2.5 hours. When traveling from Kihei in July, plan for little chillier days in Koloa, with highs around 84°F, while nights are about the same with lows around 74°F. Finish your sightseeing early on the 21st (Thu) to allow enough time to fly to Honolulu.
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Parks · Outdoors · Beaches · Nature
Side Trips

Honolulu, Oahu — 10 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
You'll enjoy a bit of beach vacationing at Waikiki Beach and Kailua Beach Park. Kids will enjoy USS Arizona Memorial and Hanauma Bay Nature Preserve. Explore the numerous day-trip ideas around Honolulu: Pupukea (Pu’u O Mahuka Heiau State Monument & Ehukai Beach Park), Lanikai Beach (in Kailua) and Haleiwa (Haleiwa Beach Park, Waimea Bay, &more). There's lots more to do: trek along Diamond Head State Monument, explore the world behind art at Honolulu Museum of Art, contemplate the long history of Battleship Missouri Memorial, and take an in-depth tour of Iolani Palace.

To find traveler tips, photos, ratings, and more tourist information, refer to the Honolulu trip planner.

You can fly from Koloa to Honolulu in 2.5 hours. In July in Honolulu, expect temperatures between 88°F during the day and 75°F at night. Wrap up your sightseeing on the 31st (Sun) to allow time to fly back home.
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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.
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