21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Fly
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Honolulu, Oahu
— 6 nights
Fly
2
Lihue, Kauai
— 3 nights
Fly
3
Kihei, Maui
— 4 nights
Fly
4
Kailua-Kona, Island of Hawaii
— 4 nights
Drive
5
Hilo, Island of Hawaii
— 2 nights
Fly

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Honolulu, Oahu

— 6 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.
You'll explore the less-touristy side of things at Makapuu Lighthouse Trail and Sharks Cove. Visit USS Arizona Memorial and Byodo-In Temple for their historical value. Get out of town with these interesting Honolulu side-trips: Pillbox Hike (in Kailua) and Sunset Beach Park (in Haleiwa). There's still lots to do: take in the spiritual surroundings of Saint Augustine by-the-Sea, see the world from above with a helicopter tour, admire the striking features of Shangri La, and get great views at Nu’uanu Pali.

Quickly create a custom-made itinerary for Honolulu using our trip planner.

New York City to Honolulu is an approximately 13.5-hour flight. You can also fly. The time zone difference moving from Eastern Standard Time to Hawaii-Aleutian Standard Time is minus 5 hours. Traveling from New York City in November, expect Honolulu to be much warmer, temps between 84°F and 72°F. Finish up your sightseeing early on the 10th (Tue) so you can catch the flight to Lihue.

Things to do in Honolulu

Outdoors · Parks · Historic Sites · Trails

Side Trips

Lihue, Kauai

— 3 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll explore the less-touristy side of things at Maha'ulepu Heritage Trail and Hanalei Bay. Get in touch with nature at Pali Ke Kua Beach (Hideaway s Beach) and Hanalei Valley Lookout. Next up on the itinerary: kick back and relax at Kalapaki Beach, indulge in some personalized pampering at some of the best spas, enjoy the sea views from Ninini Point Lighthouse Cache Site, and take in the dramatic natural features at Makawehi Bluff.

Quickly create a custom-made itinerary for Lihue using our trip planner.

Fly from Honolulu to Lihue in 2.5 hours. Alternatively, you can fly. In November in Lihue, expect temperatures between 81°F during the day and 71°F at night. Wrap up your sightseeing on the 13th (Fri) early enough to fly to Kihei.

Things to do in Lihue

Outdoors · Parks · Beaches · Trails

Side Trips

Kihei, Maui

— 4 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.
Visiting Kamaole Beach Park III and Ulua Beach will get you outdoors. Your itinerary includes some good beach time at Kamaole Beach Park II and Kamaole Beach Park I. There's much more to do: enjoy the sand and surf at Keawakapu Beach, tour the pleasant surroundings at Maluaka Beach, see majestic marine mammals with Maui Kayaks, and work some fitness into your day at Wailea Beach Path.

To see photos, reviews, other places to visit, and tourist information, read Kihei vacation maker website.

Getting from Lihue to Kihei by flight takes about 3.5 hours. Other options: fly. In November, daily temperatures in Kihei can reach 84°F, while at night they dip to 68°F. Finish up your sightseeing early on the 17th (Tue) so you can catch the flight to Kailua-Kona.

Things to do in Kihei

Outdoors · Parks · Beaches · Adventure

Side Trips

Kailua-Kona, Island of Hawaii

— 4 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.
Your cultural itinerary includes sights like St. Michael the Archangel Church and Puukohola National Historic Park. Step off the beaten path and head to Manta Adventures and Four Seasons Resort Hualalai Golf Course. Change things up with a short trip to Waialea Beach in Waimea (about 46 minutes away). There's still lots to do: tour the pleasant surroundings at Kanaloa Octopus Farm and kick back and relax at Mauna Kea Beach.

To see where to stay, other places to visit, maps, and tourist information, you can read our Kailua-Kona online trip itinerary maker.

Traveling by flight from Kihei to Kailua-Kona takes 2.5 hours. In November in Kailua-Kona, expect temperatures between 84°F during the day and 73°F at night. Finish your sightseeing early on the 21st (Sat) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Wildlife

Side Trips

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 22nd (Sun): kick back and relax at Laupahoehoe Beach Park, kick your exploration up a notch at Hawaii Zipline Tours, take in nature's colorful creations at Liliuokalani Gardens, then cruise along Banyan Drive, and finally explore the different monuments and memorials at Alae Cemetery. Get ready for a full day of sightseeing on the next day: explore the fascinating underground world of Kaumana Caves Park, then enjoy the sand and surf at Carlsmith Beach Park, and then take in the spiritual surroundings of Hilo Daijingu.

For traveler tips, maps, other places to visit, and more tourist information, use the Hilo online holiday planner.

You can drive from Kailua-Kona to Hilo in 2 hours. Other options are to drive; or take a bus. Traveling from Kailua-Kona in November, plan for slightly colder nights in Hilo, with lows around 68°F. Wrap up your sightseeing on the 23rd (Mon) to allow time to fly back home.

Things to do in Hilo

Outdoors · Parks · Historic Sites · Adventure

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.