21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

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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.
Explore hidden gems such as Lanikai Beach and Helicopter Tours. You'll enjoy a bit of beach vacationing at Kailua Beach Park and Ala Moana Beach Park. Explore the numerous day-trip ideas around Honolulu: Byodo-In Temple (in Kaneohe), Sharks Cove (in Pupukea) and Haleiwa (Laniakea Beach, Sunset Beach Park, &more). There's still lots to do: get a dose of the wild on a nature and wildlife tour, identify plant and animal life at Wildlife Areas, appreciate the extensive heritage of Makapuu Lighthouse Trail, and kick back and relax at Turtle Bay Beach.

To find traveler tips, more things to do, reviews, and more tourist information, read Honolulu trip builder tool.

Seattle to Honolulu is an approximately 8-hour flight. The time zone difference moving from Pacific Standard Time (PST) to Hawaii-Aleutian Standard Time (HST) is minus 2 hours. Expect a bit warmer temperatures when traveling from Seattle in May; daily highs in Honolulu reach 84°F and lows reach 71°F. Wrap up your sightseeing on the 8th (Sat) to allow time to travel to Lihue.

Things to do in Honolulu

Outdoors · Parks · Beaches · Tours

Side Trips

Lihue, Kauai

— 3 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Get outdoors at Wailua Falls and Scuba & Snorkeling. Your itinerary includes some good beach time at Hanalei Beach and Kalapaki Beach. Explore the numerous day-trip ideas around Lihue: Aloha Spice Company (in Hanapepe) and Na Pali Coast State Park (in Wainiha). And it doesn't end there: trek along Maha'ulepu Heritage Trail, stroll through Hanalei Bay, experience rural life at Kauai Coffee Company, and admire the sheer force of Opaekaa Falls.

For more things to do, reviews, other places to visit, and tourist information, go to the Lihue trip planner.

Traveling by flight from Honolulu to Lihue takes 2.5 hours. Expect a daytime high around 82°F in May, and nighttime lows around 71°F. Cap off your sightseeing on the 11th (Tue) early enough to travel to Kailua-Kona.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

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.
You'll discover tucked-away gems like Fishing Charters & Tours and Kanaloa Octopus Farm. Your itinerary includes some good beach time at Hapuna Beach State Recreation Area and Honaunau Bay. Change things up with these side-trips from Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau), 49 Black Sand Beach (in Waikoloa) and Kealakekua Bay (in Captain Cook). It doesn't end there: enjoy the sand and surf at Manini'owali Beach (Kua Bay) and experience rural life at Hula Daddy Kona Coffee.

For more things to do, other places to visit, maps, and tourist information, use the Kailua-Kona trip itinerary site.

You can fly from Lihue to Kailua-Kona in 2.5 hours. In May, plan for daily highs up to 83°F, and evening lows to 73°F. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

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.
Kick off your visit on the 15th (Sat): kick back and relax at Richardson Beach Park, examine the collection at Pacific Tsunami Museum, identify plant and animal life at Hawaii Tropical Botanical Garden, then take in nature's colorful creations at Liliuokalani Gardens, and finally take in the dramatic scenery at Rainbow Falls. Get ready for a full day of sightseeing on the 16th (Sun): explore the striking landscape at Thurston Lava Tube (Nahuku), hike along Kilauea Iki Trailhead, then see the interesting displays at Jagger Museum, and finally contemplate the geological forces at Kīlauea.

To see ratings, traveler tips, other places to visit, and other tourist information, use the Hilo visit planner.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. Traveling from Kailua-Kona in May, you can expect nighttime temperatures to be little chillier in Hilo, with lows of 67°F. Finish your sightseeing early on the 16th (Sun) to allow enough time to travel to Kihei.

Things to do in Hilo

Parks · Nature · Outdoors · Beaches

Side Trips

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.
Your itinerary includes some good beach time at Napili Beach and Kamaole Beach Park II. Escape the urban bustle at Zipline and Kapalua Beach. Explore the numerous day-trip ideas around Kihei: Lahaina (Hale Pa'i Printing Museum & Kapalua Coastal Trail), Haliimaile Distilling Company (in Makawao) and Parasailing & Paragliding (in Ka'anapali). There's still lots to do: enjoy the sand and surf at Keawakapu Beach, tour the pleasant surroundings at Makena Beach, indulge your thirst for a good beer at Maui Brewing Company, and take an in-depth tour of Story of Hawaii Museum.

To find maps, where to stay, ratings, and tourist information, read Kihei visit planning website.

Getting from Hilo to Kihei by flight takes about 3 hours. In May in Kihei, expect temperatures between 86°F during the day and 68°F at night. Wrap up your sightseeing by early afternoon on the 21st (Fri) to allow enough time to travel back home.

Things to do in Kihei

Outdoors · Parks · Beaches · 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.