60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
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Fly
1
Kailua-Kona, Island of Hawaii
— 12 nights
Drive
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Hilo, Island of Hawaii
— 12 nights
Fly
3
Kihei, Maui
— 13 nights
Fly
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Honolulu, Oahu
— 13 nights
Fly
5
Lihue, Kauai
— 9 nights
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Kailua-Kona, Island of Hawaii — 12 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.
Family-friendly places like Swim with Dolphins and Papakōlea Green Sand Beach will thrill your kids. Get out of town with these interesting Kailua-Kona side-trips: Captain Cook (Big Island Bees, Two Step, &more), Statue "King Kamehameha" (in Kapaau) and Honaunau (Pu'uhonua O Honaunau National Historical Park & The 1871 Trail). And it doesn't end there: Head underground at Kula Kai Caverns, tour the pleasant surroundings at Kona Cloud Forest, kick back and relax at Hapuna Beach State Recreation Area, and explore the wealth of natural beauty at Puukohola National Historic Park.

To see traveler tips, photos, more things to do, and tourist information, go to the Kailua-Kona trip maker tool.

San Francisco to Kailua-Kona is an approximately 7-hour flight. The time zone changes from Pacific Standard Time (PST) to Hawaii-Aleutian Standard Time (HST), which is usually a -2 hour difference. Traveling from San Francisco in August, expect Kailua-Kona to be a bit warmer, temps between 87°F and 77°F. Finish your sightseeing early on the 12th (Sun) so you can drive to Hilo.
Parks · Outdoors · Beaches · Nature
Side Trips

Hilo, Island of Hawaii — 12 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.
Attractions like Akaka Falls State Park and Liliuokalani Gardens make great kid-friendly stops. Venture out of the city with trips to Waipiʻo Valley Lookout (in Honokaa), Volcano (Jagger Museum & Akatsuka Orchid Gardens) and Hawaii Volcanoes National Park (Napau-Makaopuhi Crater Trail, Sulphur Banks, &more). There's lots more to do: take in the dramatic scenery at Rainbow Falls, see the sky in a new way at Imiloa Astronomy Center, get outside with Pu'u 'O'o Vent, and browse the fresh offerings at Hilo Farmers Market.

To find more things to do, maps, reviews, and tourist information, refer to the Hilo route builder app.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in September, Hilo is little chillier at night with lows of 71°F. Wrap up your sightseeing on the 24th (Fri) early enough to fly to Kihei.
Parks · Outdoors · Trails · Nature
Side Trips

Kihei, Maui — 13 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 Haleakala Crater and Maui Ocean Center. Explore the numerous day-trip ideas around Kihei: Pipiwai Trail (in Haleakala National Park), Lahaina (Lahaina Banyan Court, Scuba & Snorkeling, &more) and Kapalua (Kapalua Beach, Kapalua Resort, &more). Spend the 7th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: kick your exploration up a notch at some of the top local zipline courses and adventure parks, tee off at Makena Golf Courses, admire the majestic nature at Iao Valley, and relax and rejuvenate at Ho'omana Spa Maui.

To see where to stay, ratings, maps, and other tourist information, go to the Kihei journey planning tool.

Traveling by flight from Hilo to Kihei takes 2.5 hours. In September in Kihei, expect temperatures between 90°F during the day and 72°F at night. Wrap up your sightseeing on the 7th (Thu) early enough to fly to Honolulu.
Outdoors · Parks · Beaches · Tours
Side Trips

Honolulu, Oahu — 13 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 visit kid-friendly attractions like Diamond Head State Monument and USS Arizona Memorial. Venture out of the city with trips to Haleiwa (Sunset Beach Park, Waimea Bay, &more), Kailua (Kailua Beach Park & Lanikai Beach) and Pu’u O Mahuka Heiau State Monument (in Pupukea). Next up on the itinerary: kick back and relax at Waikiki Beach, work some fitness into your day at Ala Moana Beach Park, tour the pleasant surroundings at Hanauma Bay Nature Preserve, and steep yourself in history at Battleship Missouri Memorial.

To see reviews, more things to do, and more tourist information, you can read our Honolulu online route builder.

Fly from Kihei to Honolulu in 2.5 hours. In October, daily temperatures in Honolulu can reach 87°F, while at night they dip to 74°F. Finish up your sightseeing early on the 20th (Wed) so you can catch the flight to Lihue.
Parks · Outdoors · Beaches · Historic Sites
Side Trips

Lihue, Kauai — 9 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Family-friendly places like Zipline and Waimea Canyon State Park will thrill your kids. Explore Lihue's surroundings by going to Polihale State Park (in Waimea), Swinging Bridge (in Hanapepe) and Na Pali Makai (in Kekaha). There's lots more to do: immerse yourself in nature at Na Pali Coast State Park, stroll around Poipu Beach Park, take an unforgettable tour with a helicopter tour, and take in nature's colorful creations at Limahuli Garden and Preserve.

To see other places to visit, ratings, traveler tips, and tourist information, you can read our Lihue day trip planner.

Getting from Honolulu to Lihue by flight takes about 2.5 hours. In October in Lihue, expect temperatures between 84°F during the day and 74°F at night. Wrap up your sightseeing by early afternoon on the 29th (Fri) to allow time for the flight back home.
Parks · Outdoors · Beaches · Nature
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.