40 days in Hawaii Itinerary

Created using Klarna Trips Hawaii holiday builder
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Train to New York JFK, Fly to Honolulu
1
Honolulu, Oahu
— 9 nights
Fly
2
Koloa, Kauai
— 7 nights
Fly
3
Lahaina, Maui
— 9 nights
Fly
4
Hilo, Island of Hawaii
— 6 nights
Drive
5
Kailua-Kona, Island of Hawaii
— 8 nights
Fly

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Honolulu, Oahu — 9 nights

Big Pineapple

You'll find plenty of places to visit near Honolulu: Haleiwa (Sunset Beach Park & Waimea Bay), Turtle Bay Beach (in Kahuku) and Pu’u O Mahuka Heiau State Monument (in Pupukea). There's still lots to do: kick back and relax at Waikiki Beach, contemplate the long history of Battleship Missouri Memorial, get a tailor-made plan with Private Tours, and get a new perspective on things with Boat Tours & Water Sports.

For photos, traveler tips, and tourist information, refer to the Honolulu visit site.

Philadelphia to Honolulu is an approximately 13-hour combination of train and flight. Due to the time zone difference, you'll gain 5 hours traveling from Philadelphia to Honolulu. In July, daily temperatures in Honolulu can reach 88°F, while at night they dip to 75°F. Cap off your sightseeing on the 10th (Mon) early enough to catch the flight to Koloa.
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Outdoors · Parks · Beaches · Museums
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Koloa, Kauai — 7 nights

Explore the numerous day-trip ideas around Koloa: Waimea (Waimea Canyon State Park, Koke'e Mountains, &more), Kekaha (Na Pali Makai & Boat Tours & Water Sports) and Kapaa (Lydgate Farms Kauai Chocolate, Photography Tours, &more).

For more things to do, ratings, photos, and tourist information, read our Koloa trip builder tool.

You can fly from Honolulu to Koloa in 2.5 hours. July in Koloa sees daily highs of 84°F and lows of 74°F at night. Finish your sightseeing early on the 17th (Mon) so you can fly to Lahaina.
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Parks · Outdoors · Beaches · Tours
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Lahaina, Maui — 9 nights

Crown Jewel of Maui

Explore the numerous day-trip ideas around Lahaina: Wailea (Wailea Beach, Maluaka Beach, &more), Kihei (Maui's World Gallery & Kamaole Beach Park III) and Wailuku (Iao Valley & Mendes Ranch). Spend the 20th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: get a new perspective on things with Boat Tours & Water Sports, tour the pleasant surroundings at Kapalua Beach, contemplate the geological forces at Haleakala Crater, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

For traveler tips, maps, reviews, and other tourist information, you can read our Lahaina online tour planner.

Getting from Koloa to Lahaina by flight takes about 2.5 hours. In July, daytime highs in Lahaina are 86°F, while nighttime lows are 73°F. Finish up your sightseeing early on the 26th (Wed) so you can catch the flight to Hilo.
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Outdoors · Parks · Beaches · Nature
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Hilo, Island of Hawaii — 6 nights

America's Wettest City

Explore Hilo's surroundings by going to Hawaii Volcanoes National Park (Volcano Art Center Gallery, Devastation Trail, &more) and Laupahoehoe Beach Park (in Laupahoehoe). Next up on the itinerary: admire the majestic nature at Akaka Falls State Park, cruise along Chain of Craters Rd, explore the fascinating underground world of Kazumura Cave Tours, and admire the sheer force of Nanue falls.

Plan my Hilo trip by asking Klarna Trips to come up with tips and suggestions.

Traveling by flight from Lahaina to Hilo takes 2.5 hours. July in Hilo sees daily highs of 85°F and lows of 71°F at night. Finish your sightseeing early on the 1st (Tue) to allow enough time to drive to Kailua-Kona.
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Parks · Outdoors · Trails · Nature
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Kailua-Kona, Island of Hawaii — 8 nights

Heart of the Kona Coast

Get out of town with these interesting Kailua-Kona side-trips: Puukohola National Historic Park (in Kawaihae), Papakōlea Green Sand Beach (in Naalehu) and Hapuna Golf Course (in Waimea). And it doesn't end there: head outdoors with Outdoor Activities, cruise along Mauna Loa Scenic Drive, explore the striking landscape of Pu'uhonua O Honaunau National Historical Park, and enjoy the sand and surf at Hapuna Beach State Recreation Area.

To find reviews, traveler tips, maps, and tourist information, go to the Kailua-Kona online road trip planner.

You can drive from Hilo to Kailua-Kona in 2 hours. Other options are to drive; or take a bus. Traveling from Hilo in August, plan for a bit warmer nights in Kailua-Kona, with lows around 77°F. Finish your sightseeing early on the 9th (Wed) so you can fly back home.
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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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