21 days in Hawaii Itinerary

Created using Inspirock Hawaii tour planner
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Fly
1
Honolulu, Oahu
— 7 nights
Fly
2
Lihue, Kauai
— 3 nights
Fly
3
Kailua-Kona, Island of Hawaii
— 3 nights
Drive
4
Hilo, Island of Hawaii
— 2 nights
Fly
5
Kihei, Maui
— 5 nights
Fly

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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.
Step off the beaten path and head to Lanikai Beach and Kailua Beach Park. Your itinerary includes some good beach time at Waimanalo Beach and Ala Moana Beach Park. Change things up with these side-trips from Honolulu: Byodo-In Temple (in Kaneohe), Shark's Cove (in Pupukea) and Haleiwa (Laniakea Beach, Sunset Beach Park, &more). The adventure continues: get interesting insight from Tours, examine the collection at USS Bowfin Submarine Museum & Park, have unforgettable encounters with a shark diving experience, and get to know the fascinating history of Makapuu Lighthouse Trail.

For reviews, ratings, and more tourist information, refer to the Honolulu day trip site.

Seattle to Honolulu is an approximately 7.5-hour flight. The time zone difference when traveling from Seattle to Honolulu is minus 2 hours. Expect much warmer temperatures when traveling from Seattle in December; daily highs in Honolulu reach 82°F and lows reach 69°F. Finish up your sightseeing early on the 1st (Sun) so you can catch the flight to Lihue.
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Side Trips
Find places to stay Dec 25 — Jan 1:

Lihue, Kauai — 3 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Relax by the water at Kalapaki Beach and Hanalei Bay. You'll explore the less-touristy side of things at Wailua Falls and Na Pali Coast State Park. Get out of town with these interesting Lihue side-trips: Aloha Spice Company (in Hanapepe) and Hanalei Beach (in Hanalei). Next up on the itinerary: stroll through Maha'ulepu Heritage Trail, take some stellar pictures from Sleeping Giant Trail, admire the sheer force of Opaekaa Falls, and experience rural life at Kauai Coffee Company.

To see maps, photos, where to stay, and more tourist information, read our Lihue trip site.

Fly from Honolulu to Lihue in 2.5 hours. January in Lihue sees daily highs of 79°F and lows of 65°F at night. Finish your sightseeing early on the 4th (Wed) to allow enough time to fly to Kailua-Kona.
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Find places to stay Jan 1 — 4:

Kailua-Kona, Island of Hawaii — 3 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.
Escape the urban bustle at Fishing Charters & Tours and Kanaloa Octopus Farm. Explore hidden gems such as Pu'uhonua O Honaunau National Historical Park and Manini'owali Beach (Kua Bay). Explore Kailua-Kona's surroundings by going to 49 Black Sand Beach (in Waikoloa), Hapuna Beach State Recreation Area (in Puako) and Kealakekua Bay (in Captain Cook). There's more to do: experience rural life at Hula Daddy Kona Coffee.

To see maps, more things to do, other places to visit, and other tourist information, read our Kailua-Kona trip planner.

You can fly from Lihue to Kailua-Kona in 2.5 hours. January in Kailua-Kona sees daily highs of 80°F and lows of 67°F at night. Finish your sightseeing early on the 7th (Sat) to allow enough time to drive to Hilo.
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Find places to stay Jan 4 — 7:

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.
Start off your visit on the 8th (Sun): kick back and relax at Richardson Beach Park, see the interesting displays at Pacific Tsunami Museum, admire the natural beauty at Hawaii Tropical Bioreserve and Garden, then take in nature's colorful creations at Liliuokalani Gardens, and finally take in the dramatic scenery at Rainbow Falls. Keep things going the next day: explore the striking landscape at Thurston Lava Tube (Nahuku), then hike along Kilauea Iki Trailhead, and then get impressive views of Kīlauea.

To see where to stay, reviews, maps, and more tourist information, read Hilo trip itinerary website.

Drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. In January, daily temperatures in Hilo can reach 81°F, while at night they dip to 64°F. Finish your sightseeing early on the 9th (Mon) so you can fly to Kihei.
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Find places to stay Jan 7 — 9:

Kihei, Maui — 5 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.
Eschew the tourist crowds and head to Zipline and Ho'okipa Beach Park. Take a break from the city and head to Napili Beach and Wailea Beach. Venture out of the city with trips to Lahaina (Hale Pa'i Printing Museum & Kapalua Coastal Trail), Kapalua Beach (in Kapalua) and Haliimaile Distilling Company (in Makawao). There's much more to do: kick back and relax at Kamaole Beach Park III, take an in-depth tour of Story of Hawaii Museum, get interesting insight from Tours, and stroll through Makena Beach.

For maps, where to stay, ratings, and more tourist information, read Kihei trip itinerary app.

Traveling by flight from Hilo to Kihei takes 2.5 hours. In January, daily temperatures in Kihei can reach 81°F, while at night they dip to 63°F. You'll have a few hours on the 14th (Sat) to wrap things up before traveling home.
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Side Trips
Find places to stay Jan 9 — 14:

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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