60 days in Hawaii Itinerary

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Fly
1
Kailua-Kona, Island of Hawaii
— 11 nights
Drive
2
Hilo, Island of Hawaii
— 5 nights
Fly
3
Honolulu, Oahu
— 15 nights
Fly
4
Koloa, Kauai
— 13 nights
Fly
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Kihei, Maui
— 14 nights
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Kailua-Kona, Island of Hawaii — 11 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 hidden gems such as Mauna Kea and Fishing Charters & Tours. Step out of the city life by going to Saddle Road and Papakōlea Green Sand Beach. You'll find plenty of places to visit near Kailua-Kona: Hapuna Beach State Recreation Area (in Puako), Captain Cook (Royal Kona Coffee Center, Kealakekua Bay, &more) and Ka Lae Light (in Naalehu). Spend the 8th (Fri) exploring nature at Kaloko-Honokohau National Historical Park. There's much more to do: kick back and relax at Manini'owali Beach (Kua Bay), stroll through Magic Sands, see the world from above with a helicopter tour, and observe the fascinating underwater world at Ocean Rider Inc.

To see where to stay, photos, reviews, and tourist information, you can read our Kailua-Kona trip planner.

Buenos Aires, Argentina to Kailua-Kona is an approximately 24-hour flight. The time zone changes from Argentina Standard Time (ART) to Hawaii-Aleutian Standard Time (HST), which is usually a -7 hour difference. Plan for much warmer temperatures traveling from Buenos Aires in September, with highs in Kailua-Kona at 36°C and lows at 28°C. Finish your sightseeing early on the 12th (Tue) so you can drive to Hilo.
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Find places to stay Sep 1 — 12:

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.
Step off the beaten path and head to Rainbow Falls and Punalu‘U Beach. Visiting Hawaii Tropical Bioreserve and Garden and Kīlauea will get you outdoors. Get out of town with these interesting Hilo side-trips: Pahoa (Steam Vents & Kapoho Tide Pools), Akatsuka Orchid Gardens (in Volcano) and Hawaii Volcanoes National Park (Kilauea Iki Trailhead & Thurston Lava Tube (Nahuku)). There's much more to do: take in nature's colorful creations at Liliuokalani Gardens, get a dose of the wild on a nature and wildlife tour, see the interesting displays at Pacific Tsunami Museum, and enjoy the sand and surf at Richardson Beach Park.

For ratings, reviews, other places to visit, and more tourist information, go to the Hilo itinerary tool.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. Plan for slightly colder nights when traveling from Kailua-Kona in September since evenings lows in Hilo dip to 25°C. Finish your sightseeing early on the 17th (Sun) so you can fly to Honolulu.
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Find places to stay Sep 12 — 17:

Honolulu, Oahu — 15 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.
Step off the beaten path and head to Swim with Dolphins and Makapuu Lighthouse Trail. Get in touch with nature at Lanikai Beach and Kapiolani Regional Park. Explore the numerous day-trip ideas around Honolulu: Ka'ena Point State Park (in Waianae), Green World Coffee Farms (in Wahiawa) and Waimanalo Beach (in Waimanalo). There's much more to do: enjoy the sand and surf at Shark's Cove, stroll through Sunset Beach Park, get some jogging in at Ala Moana Beach Park, and indulge in some culinary diversions at a local gastronomic tour.

To find reviews, where to stay, more things to do, and more tourist information, use the Honolulu trip planner.

Traveling by flight from Hilo to Honolulu takes 2.5 hours. In September, daily temperatures in Honolulu can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 2nd (Mon) so you can fly to Koloa.
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Find places to stay Sep 17 — Oct 2:

Koloa, Kauai — 13 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Escape the urban bustle at Poipu Beach Park and Wailua Falls. Explore hidden gems such as Scuba & Snorkeling and Hanalei Beach. You'll find plenty of places to visit near Koloa: Kapaa (Sleeping Giant Trail, Kauai Path, &more), Polihale State Park (in Waimea) and Princeville (Hanalei Valley Lookout & Pali Ke Kua Beach (Hideaway s Beach)). There's lots more to do: stroll through Kalalau Trail, enjoy the sand and surf at Hanalei Bay, make a trip to Kalalau Lookout, and immerse yourself in nature at Na Pali Coast State Park.

Find out how to plan Koloa trip without stress by asking Klarna Trips to help create an itinerary.

You can fly from Honolulu to Koloa in 2.5 hours. In October in Koloa, expect temperatures between 34°C during the day and 27°C at night. Cap off your sightseeing on the 15th (Sun) early enough to catch the flight to Kihei.
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Find places to stay Oct 2 — 15:

Kihei, Maui — 14 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.
We've included these beaches for you: Ho'okipa Beach Park and Kamaole Beach Park II. Get in touch with nature at Zipline and Nakalele Blowhole. Explore the numerous day-trip ideas around Kihei: Paia (Mantokuji Temple Mission of Paia & Lower Paia Park), Kapalua (Kapalua Beach & D.T. Fleming Park) and Lahaina (Napili Beach, Hale Pa'ahao - Old Lahaina Prison, &more). Next up on the itinerary: enjoy the sand and surf at Makena Beach, tour the pleasant surroundings at Ulua Beach, look for all kinds of wild species at Pools at Ohe'o, and discover the deep blue sea with a scuba or snorkeling tour.

For where to stay, photos, more things to do, and tourist information, use the Kihei trip planner.

Traveling by flight from Koloa to Kihei takes 2.5 hours. In October, daily temperatures in Kihei can reach 36°C, while at night they dip to 24°C. Wrap up your sightseeing on the 29th (Sun) to allow time to fly back home.
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Find places to stay Oct 15 — 29:

Hawaii travel guide

4.4
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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