21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

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

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Honolulu, Oahu — 7 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.
Change things up with these side-trips from Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Waimea Bay & Sunset Beach Park). The adventure continues: go for a walk through Diamond Head State Monument, capture your vacation like a pro with an inspiring photography tour, steep yourself in history at Battleship Missouri Memorial, and discover the deep blue sea with a scuba or snorkeling tour.

To see traveler tips, more things to do, other places to visit, and other tourist information, use the Honolulu day trip website.

Washington to Honolulu is an approximately 12.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST), which is usually a -5 hour difference. In May, Honolulu is somewhat warmer than Washington - with highs of 84°F and lows of 71°F. Finish up your sightseeing early on the 14th (Sun) so you can catch the flight to Kailua-Kona.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay May 7 — 14:
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Kailua-Kona, Island of Hawaii — 2 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.
Start off your visit on the 15th (Mon): kick back and relax at Hapuna Beach State Recreation Area and then enjoy the sand and surf at Mauna Kea Beach. On the next day, experience rural life at The Vanillerie, contemplate in the serene atmosphere at Mokuaikaua Church, then get a new perspective on things with Boat Tours & Water Sports, and finally indulge your thirst for a good beer at Ola Brew.

To find more things to do, other places to visit, reviews, and tourist information, you can read our Kailua-Kona trip itinerary website.

Traveling by flight from Honolulu to Kailua-Kona takes 2.5 hours. In May in Kailua-Kona, expect temperatures between 83°F during the day and 73°F at night. Wrap up your sightseeing on the 16th (Tue) to allow time to drive to Hilo.
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Outdoors · Beaches · Parks · Nature
Side Trips
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Hilo, Island of Hawaii — 2 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.
On the 17th (Wed), examine the collection at Pacific Tsunami Museum, take a memorable drive along Devastation Trail, then stroll through Kilauea Iki Trailhead, and finally trek along Kipuka Puaulu (Bird Park) Trail. Keep things going the next day: get up close and personal with brilliant marine life at Mokupapapa Discovery Center, take in nature's colorful creations at Liliuokalani Gardens, pick up some local products at Hilo Farmers Market, then admire the sheer force of Akaka Falls State Park, and finally admire the sheer force of Rainbow Falls.

For maps, photos, traveler tips, and more tourist information, use the Hilo trip maker website.

You can drive from Kailua-Kona to Hilo in 2 hours. Another option is to take a bus. Traveling from Kailua-Kona in May, expect slightly colder with lows of 67°F in Hilo. Finish your sightseeing early on the 18th (Thu) so you can fly to Lahaina.
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Parks · Outdoors · Trails · Nature
Side Trip
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Lahaina, Maui — 5 nights

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Get out of town with these interesting Lahaina side-trips: Iao Valley (in Wailuku), Kalepolepo Beach Park (in Kihei) and Haleakala Crater (in Haleakala National Park). Spend the 19th (Fri) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, kick back and relax at Kapalua Beach, stroll around Lahaina Banyan Court, and whizz through the canopy at some of the top local zipline courses and adventure parks.

To find photos, where to stay, maps, and more tourist information, refer to the Lahaina day trip site.

Getting from Hilo to Lahaina by flight takes about 2.5 hours. Expect a daytime high around 81°F in May, and nighttime lows around 70°F. Finish up your sightseeing early on the 23rd (Tue) so you can catch the flight to Koloa.
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Outdoors · Parks · Beaches · Scenic Drive
Side Trips
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Koloa, Kauai — 4 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Get out of town with these interesting Koloa side-trips: Boat Tours & Water Sports (in Kekaha), Wai`oli Hui`ia Church (in Hanalei) and Waimea (Waimea Canyon State Park, Koke'e Mountains, &more). There's much more to do: admire the majestic nature at Na Pali Coast State Park, play a few rounds at Poipu Bay Resort Golf Course, take an unforgettable tour with a helicopter tour, and take in the dramatic natural features at Spouting Horn.

For traveler tips, other places to visit, maps, and other tourist information, read Koloa trip itinerary builder app.

Getting from Lahaina to Koloa by flight takes about 2.5 hours. May in Koloa sees daily highs of 82°F and lows of 71°F at night. Wrap up your sightseeing on the 27th (Sat) early enough to travel back home.
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Side Trips
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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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