21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner

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Route & dates

Start: Sydney
Fly:  14 h 45 min
1
Kailua-Kona, Island of Hawaii
— 5 nights
Bus + Fly:  3 h 45 min
2
Honolulu, Oahu
— 7 nights
Fly:  2 h 30 min
3
Kihei, Maui
— 4 nights
Drive:  45 min
4
Lahaina, Maui
— 3 nights
Fly:  14 h 30 min
End: Sydney

5
nights
Kailua-Kona, Island of Hawaii

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 visit kid-friendly attractions like Liliuokalani Gardens and White Sand Beach. You'll explore the less-touristy side of things at Fishing Charters & Tours and Kanaloa Octopus Farm. Explore Kailua-Kona's surroundings by going to Waialea Beach (in Waimea), Kealakekua Bay (in Captain Cook) and Hilo (Akaka Falls State Park, Rainbow Falls, &more). There's much more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, get great views at Pololu Valley Lookout, explore the fascinating underground world of Lava Tube Cave, and kick back and relax at Magic Sands.

To see where to stay, ratings, reviews, and other tourist information, use the Kailua-Kona trip planner.

Sydney, Australia to Kailua-Kona is an approximately 15.5- hour flight. You can also do a combination of flight and bus; or do a combination of train, bus, and flight. The time zone difference moving from Australian Eastern Standard Time to Hawaii Standard Time is minus 20 hours. Plan for much hotter temperatures traveling from Sydney in July, with highs in Kailua-Kona at 35°C and lows at 28°C. Finish your sightseeing early on the 6th (Mon) so you can travel to Honolulu.

Things to do in Kailua-Kona

Outdoors Parks Wildlife

Side Trips

Hilo, Island of Hawaii, Waialea Beach, Kealakekua Bay, Kahaluu Beach
Highlights from your plan
Swim with Dolphins
Fishing Charters & Tours
Waipio Valley ©
Waipio Valley

7
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Head to Honolulu Cookie Company Hilton Hawaiian Village and Saturday Farmer's Market KCCfor plenty of shopping. Get in touch with nature at Diamond Head State Monument and Lanikai Beach. Change things up with these side-trips from Honolulu: Pupukea (Sharks Cove & Banzai Pipeline), Kayaking & Canoeing (in Kailua) and Haleiwa (Laniakea Beach, Skydiving, &more). There's lots more to do: enjoy the sand and surf at Kapiolani Regional Park, stroll the grounds of National Memorial Cemetery of the Pacific, look for all kinds of wild species at Hanauma Bay Nature Preserve, and trek along Koko Crater Railway Trail.

For where to stay, maps, photos, and tourist information, you can read our Honolulu online vacation maker.

You can do a combination of bus and flight from Kailua-Kona to Honolulu in 4 hours. Alternatively, you can fly. Expect a daytime high around 36°C in July, and nighttime lows around 28°C. Finish your sightseeing early on the 13th (Mon) to allow enough time to travel to Kihei.

Things to do in Honolulu

Outdoors Parks Tours

Side Trips

Haleiwa, Pupukea, Kailua
Highlights from your plan
Lanikai Beach ©
Lanikai Beach
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Nature & Wildlife Tours

4
nights
Kihei, Maui

Kihei ©
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.
Escape the urban bustle at Kamaole Beach Park II and Haleakala Crater. Visit Ulua Beach and Cove Park for some beach relaxation. Next up on the itinerary: kick back and relax at Kamaole Beach Park III, cruise along Haleakala Highway (Crater Road), tour the pleasant surroundings at Big Beach, and delve into the lush surroundings at Bamboo Forest.

To see traveler tips, more things to do, reviews, and tourist information, refer to the Kihei trip maker.

Traveling by flight from Honolulu to Kihei takes 2.5 hours. Alternatively, you can do a combination of flight and taxi; or do a combination of flight and car. In July in Kihei, expect temperatures between 37°C during the day and 26°C at night. Wrap up your sightseeing by early afternoon on the 17th (Fri) to allow enough time to drive to Lahaina.

Things to do in Kihei

Parks Outdoors Beaches

Side Trips

Maui, Ulua Beach, Haleakala Crater
Highlights from your plan
Ulua Beach ©
Ulua Beach
Kamaole Beach Park II ©
Kamaole Beach Park II
Kamaole Beach Park III ©
Kamaole Beach Park III

3
nights
Lahaina, Maui

Lahaina ©
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.
Your inner history buff will appreciate Maria Lanakila Catholic Church and Sacred Hearts Mission Church. Escape the urban bustle at Nakalele Blowhole and Honolua Bay. There's still lots to do: enjoy the sand and surf at Kapalua Beach, view the masterpieces at Lahaina Galleries, glide through the air with a parasailing or paragliding tour, and pause for some serene contemplation at Lahaina United Methodist Church.

For photos, where to stay, maps, and other tourist information, you can read our Lahaina trip itinerary planner.

Drive from Kihei to Lahaina in an hour. Alternatively, you can do a combination of taxi and bus. July in Lahaina sees daily highs of 35°C and lows of 26°C at night. You'll have a few hours on the 20th (Mon) to wrap things up before traveling home.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Kapalua, Maui, Parasailing & Paragliding
Highlights from your plan
Kapalua Beach ©
Kapalua Beach
Parasailing & Paragliding
Old Lahaina Courthouse ©
Old Lahaina Courthouse

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