21 days in Hawaii Itinerary

Created using Inspirock Hawaii trip 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
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Honolulu, Oahu — 7 nights

Big Pineapple

Take a break from the city and head to Lanikai Beach and Photography Tours. Discover out-of-the-way places like Koko Crater Railway Trail and Waimanalo Beach. You'll find plenty of places to visit near Honolulu: Shark's Cove (in Pupukea), Turtle Bay Beach (in Kahuku) and Haleiwa (Laniakea Beach, Sunset Beach Park, &more). There's lots more to do: meet some fierce fish with a shark diving experience, enjoy the sand and surf at Ala Moana Beach Park, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, and examine the collection at USS Bowfin Submarine Museum & Park.

Discover how to plan a Honolulu trip in just a few steps with Inspirock's itinerary builder.

Seattle to Honolulu is an approximately 7.5-hour flight. Due to the time zone difference, you'll gain 2 hours traveling from Seattle to Honolulu. Prepare for much warmer weather when traveling from Seattle in October: high temperatures in Honolulu hover around 36°C and lows are around 27°C. Finish up your sightseeing early on the 12th (Thu) so you can catch the flight to Lihue.
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Find places to stay Oct 5 — 12:

Lihue, Kauai — 3 nights

Discover out-of-the-way places like Wailua Falls and Hanalei Beach. Step out of the city life by going to Na Pali Coast State Park and Sleeping Giant Trail. When in Lihue, make a side trip to see Aloha Spice Company in Hanapepe, approximately Hanapepe away.

To find reviews, maps, traveler tips, and other tourist information, use the Lihue sightseeing planner.

Getting from Honolulu to Lihue by flight takes about 2.5 hours. October in Lihue sees daily highs of 34°C and lows of 27°C at night. Finish up your sightseeing early on the 15th (Sun) so you can catch the flight to Kailua-Kona.
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Find places to stay Oct 12 — 15:

Kailua-Kona, Island of Hawaii — 3 nights

Heart of the Kona Coast

You'll get in some beach time at Pu'uhonua O Honaunau National Historical Park and 49 Black Sand Beach. Get outdoors at Fishing Charters & Tours and Kealakekua Bay. Take a break from Kailua-Kona with a short trip to Hapuna Beach State Recreation Area in Puako, about 48 minutes away. There's much more to do: enjoy the sand and surf at Manini'owali Beach (Kua Bay), relax in the rural setting at Hula Daddy Kona Coffee, and look for all kinds of wild species at Kanaloa Octopus Farm.

For ratings, more things to do, traveler tips, and tourist information, refer to the Kailua-Kona travel route planner.

Traveling by flight from Lihue to Kailua-Kona takes 2.5 hours. Expect a daytime high around 35°C in October, and nighttime lows around 28°C. Finish your sightseeing early on the 18th (Wed) so you can drive to Hilo.
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Find places to stay Oct 15 — 18:

Hilo, Island of Hawaii — 2 nights

America's Wettest City

On the 19th (Thu), enjoy the sand and surf at Richardson Beach Park, examine the collection at Pacific Tsunami Museum, then identify plant and animal life at Hawaii Tropical Bioreserve and Garden, then admire the natural beauty at Liliuokalani Gardens, and finally admire the sheer force of Rainbow Falls. Get ready for a full day of sightseeing on the next day: take in the dramatic natural features at Thurston Lava Tube (Nahuku), then hike along Kilauea Iki Trailhead, and then get impressive views of Kīlauea.

To find other places to visit, traveler tips, maps, and more tourist information, use the Hilo road trip planning app.

Getting from Kailua-Kona to Hilo by car takes about 1.5 hours. Other options: take a bus. Traveling from Kailua-Kona in October, you can expect nighttime temperatures to be little chillier in Hilo, with lows of 24°C. Finish your sightseeing early on the 20th (Fri) so you can fly to Kihei.
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Find places to stay Oct 18 — 20:

Kihei, Maui — 5 nights

Eschew the tourist crowds and head to Zipline and Ho'okipa Beach Park. Visiting Wailea Beach and Parasailing & Paragliding will get you outdoors. You'll find plenty of places to visit near Kihei: Haliimaile Distilling Company (in Makawao), Kapalua Beach (in Kapalua) and Lahaina (Hale Pa'i Printing Museum, Napili Beach, &more). There's much more to do: stroll through Kamaole Beach Park III, kick back and relax at Makena Beach, take an in-depth tour of Story of Hawaii Museum, and sample the tasty concoctions at Maui Brewing Company.

To see reviews, ratings, traveler tips, and other tourist information, read Kihei day trip planning website.

Fly from Hilo to Kihei in 2.5 hours. In October, plan for daily highs up to 36°C, and evening lows to 24°C. You will have some time to spend on the 25th (Wed) before leaving for home.
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Find places to stay Oct 20 — 25:

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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