39 days in Hawaii Itinerary

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

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Kailua-Kona, Island of Hawaii — 7 nights

Heart of the Kona Coast

Relax by the water at Pu'uhonua O Honaunau National Historical Park and Hapuna Beach State Recreation Area. Get outdoors at Swim with Dolphins and Mauna Kea Beach. Venture out of the city with trips to Waimea (Waialea Beach, Hapuna Golf Course, &more), Mauna Loa Scenic Drive (in Hawaii Volcanoes National Park) and Puukohola National Historic Park (in Kawaihae). And it doesn't end there: look for gifts at Waikoloa Beach Resort, kick back and relax at Papakōlea Green Sand Beach, get a tailor-made plan with Private Tours, and stroll through Anaehoomalu.

For ratings, reviews, other places to visit, and other tourist information, read Kailua-Kona day trip planning site.

Minneapolis to Kailua-Kona is an approximately 11-hour flight. The time zone difference when traveling from Minneapolis to Kailua-Kona is minus 4 hours. In February, Kailua-Kona is much hotter than Minneapolis - with highs of 81°F and lows of 69°F. Wrap up your sightseeing on the 28th (Tue) to allow time to drive to Hilo.
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Outdoors · Parks · Beaches · Wildlife
Side Trips

Hilo, Island of Hawaii — 4 nights

America's Wettest City

For shopping fun, head to Volcano Art Center Gallery or Banyan Gallery. Get in touch with nature at Nature & Wildlife Tours and Devastation Trail. Explore the numerous day-trip ideas around Hilo: Hawaii Volcanoes National Park (Sulphur Banks, Kīlauea, &more). There's still lots to do: admire the majestic nature at Akaka Falls State Park, admire the natural beauty at Liliuokalani Gardens, admire the sheer force of Rainbow Falls, and look for gifts at Big Island Candies.

To find photos, maps, other places to visit, and more tourist information, go to the Hilo planning app.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: drive; or take a bus. In February, plan for daily highs up to 81°F, and evening lows to 65°F. Finish up your sightseeing early on the 4th (Sat) so you can catch the flight to Lahaina.
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Parks · Outdoors · Trails · Wildlife
Side Trips

Lahaina, Maui — 10 nights

Crown Jewel of Maui

We've included these beaches for you: Ka'anapali Beach and Makena Beach. Get in touch with nature at Scuba & Snorkeling and Haleakala Crater. You'll find plenty of places to visit near Lahaina: Paia (Paia Peace Stupa & HA Baldwin Beach Park), Haleakala Observatories (in Haleakala National Park) and Kihei (Kamaole Beach Park III & Makena Golf Courses). Spend the 14th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: get up close and personal with brilliant marine life at Maui Ocean Center, view the masterpieces at Reeflections Fine Art Gallery, enjoy the sand and surf at Wailea Beach, and tour the pleasant surroundings at Napili Beach.

To find ratings, more things to do, and tourist information, read Lahaina driving holiday planning site.

Getting from Hilo to Lahaina by flight takes about 2.5 hours. Expect a daytime high around 78°F in March, and nighttime lows around 67°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to fly to Koloa.
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Outdoors · Parks · Beaches · Shopping
Side Trips

Koloa, Kauai — 7 nights

Head to Art House Hawaii and Poipu Shopping Villagefor plenty of shopping. Visiting Waimea Canyon State Park and Na Pali Coast State Park will get you outdoors. Change things up with these side-trips from Koloa: Princeville Center (in Princeville), Waimea (Puu Hinahina Lookout, Aloha 'n Paradise Espresso Bar, &more) and Hanalei Beach (in Hanalei).

For traveler tips, other places to visit, reviews, and more tourist information, go to the Koloa trip planner.

Getting from Lahaina to Koloa by flight takes about 2.5 hours. March in Koloa sees daily highs of 78°F and lows of 66°F at night. Finish your sightseeing early on the 21st (Tue) so you can fly to Honolulu.
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Parks · Outdoors · Beaches · Shopping
Side Trips

Honolulu, Oahu — 10 nights

Big Pineapple

You'll enjoy a bit of beach vacationing at Waikiki Beach and Sunset Beach Park. For shopping fun, head to Ala Moana Center or Don Quijote. Explore the numerous day-trip ideas around Honolulu: Waianae (Makaha Beach Park, Swim with Dolphins, &more), Haleiwa (Haleiwa Beach Park, Wys Galleries, &more) and Pupukea (Pu’u O Mahuka Heiau State Monument, Banzai Pipeline, &more). There's much more to do: explore the different monuments and memorials at USS Arizona Memorial, enjoy the sand and surf at Ala Moana Beach Park, tour the pleasant surroundings at Turtle Bay Beach, and take in the dramatic scenery at Manoa Falls.

To find where to stay, more things to do, and other tourist information, you can read our Honolulu trip itinerary planner.

You can fly from Koloa to Honolulu in 2.5 hours. In March, daytime highs in Honolulu are 81°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 31st (Fri) early enough to fly back home.
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Parks · Outdoors · Beaches · Shopping
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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