60 days in Maui & Oahu's Windward Coast Itinerary

60 days in Maui & Oahu's Windward Coast Itinerary

Created using Inspirock Hawaii trip planner

Plan created by another user.Make it yours

Route & dates

Start: Sydney
Fly:  14 h 30 min
1
Lahaina
— 22 nights
Drive:  2 h 30 min
2
Hana
— 17 nights
Fly:  4 h 30 min
3
Kailua
— 19 nights
Fly:  14 h
End: Sydney

22
nights
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.
Venture out of the city with trips to Kihei (Saint Theresa Roman Catholic Church, Scuba & Snorkeling, &more), Wailea (Oneloa Beach, Wailea Beach, &more) and Wailuku (Iao Valley, Hale Ho'ike'ike at the Bailey House, &more). There's lots more to do: kick back and relax at Ka'anapali Beach, tour the pleasant surroundings at Napili Beach, take a memorable tour with Tours, and experience rural life at Punakea Palms.

For maps, where to stay, more things to do, and more tourist information, you can read our Lahaina trip builder site.

Sydney, Australia to Lahaina is an approximately 16.5-hour flight. The time zone changes from Australian Eastern Standard Time to Hawaii Standard Time, which is usually a -20 hour difference. In December, daily temperatures in Lahaina can reach 30°C, while at night they dip to 23°C. Wrap up your sightseeing on the 23rd (Mon) to allow time to drive to Hana.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Kihei, Wailea, Wailuku, Maui, Kapalua
Find places to stay Nov 30 — Dec 23:
Highlights from your plan
Scuba & Snorkeling
Ka'anapali Beach ©
Ka'anapali Beach
Lahaina Banyan Court ©
Lahaina Banyan Court

17
nights
Hana

Hana ©
Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
Change things up with these side-trips from Hana: Haiku (Hana Lava Tubes, Zipline, &more), Huialoha Church (in Kaupo) and Haleakala National Park (Haleakala Crater & Sliding Sands Trail). Spend the 25th (Wed) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: kick back and relax at Wai'anapanapa State Park, don't miss a visit to Kalaloa Point, take in the exciting artwork at Laura Mango Art Gallery, and take a peaceful walk through Makawao Forest Reserve.

For where to stay, traveler tips, photos, and tourist information, you can read our Hana tour website.

Getting from Lahaina to Hana by car takes about 3 hours. Other options: fly; or do a combination of bus and car. In December, daytime highs in Hana are 32°C, while nighttime lows are 22°C. Finish your sightseeing early on the 9th (Thu) so you can travel to Kailua.

Things to do in Hana

Parks Outdoors Nature

Side Trips

Maui, Haiku, Haleakala National Park, Kipahulu, Kula
Find places to stay Dec 23 — Jan 9:
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Hana Coast Gallery ©
Hana Coast Gallery

19
nights
Kailua

Kailua is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Explore the numerous day-trip ideas around Kailua: Kaneohe (Hawaiian Memorial Park Cemetery & Funeral Services & Senator Fong's Plantation and Gardens), Haleiwa (Waimea Bay, Sunset Beach Park, &more) and Hauula (Hauula Loop Trail & Kokololio Beach Park). There's much more to do: don't miss a visit to Polynesian Cultural Center, kick back and relax at Turtle Bay Beach, fulfill a lifelong dream with a swim-with-the-dolphins experience, and admire the natural beauty at Hoomaluhia Botanical Gardens.

To find maps, other places to visit, and tourist information, read Kailua trip itinerary website.

You can fly from Hana to Kailua in 4.5 hours. Traveling from Hana in January, you can expect nighttime temperatures to be somewhat warmer in Kailua, with lows of 24°C. Wrap up your sightseeing by early afternoon on the 28th (Tue) to allow time for travel back home.

Things to do in Kailua

Parks Outdoors Beaches

Side Trips

Kaneohe, Waimanalo, Haleiwa, Oahu, Hauula
Find places to stay Jan 9 — 28:
Highlights from your plan
Swim with Dolphins
Polynesian Cultural Center ©
Polynesian Cultural Center
Kailua Beach Park ©
Kailua Beach Park

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