60 days in Maui & Oahu's Windward Coast Itinerary

60 days in Maui & Oahu's Windward Coast Itinerary

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Route & dates

60 days in Maui & Oahu's Windward Coast Itinerary

Start: Sydney
Fly:  14​h 30​min
1
Lahaina
— 22 nights
bus + 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

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.
Explore the numerous day-trip ideas around Lahaina: Wailea (Oneloa Beach, Wailea Beach, & more), Kihei (Saint Theresa Roman Catholic Church, Scuba & Snorkeling, & more) and Wailuku (Iao Valley, Hale Ho'ike'ike at the Bailey House, & more). There's lots more to do: stroll through Ka'anapali Beach, enjoy the sand and surf at Napili Beach, don't miss a visit to Lahaina Banyan Court, and whizz through the canopy at some of the top local zipline courses and adventure parks.

To see more things to do, where to stay, ratings, and more tourist information, you can read our Lahaina online visit planner .

Sydney, Australia to Lahaina is an approximately 14.5-hour flight. You can also do a combination of flight and bus. You'll gain 20 hours traveling from Sydney to Lahaina due to the time zone difference. In December in Lahaina, expect temperatures between 30°C during the day and 23°C at night. Finish your sightseeing early on the 23rd (Mon) to allow enough time to travel to Hana.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

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

17
nights
Hana

Hana ©
Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
Explore the numerous day-trip ideas around Hana: Haleakala National Park (Haleakala Crater & Sliding Sands Trail), Haiku (Zipline, Venus Pool (Waioka Pond), & more) and Huialoha Church (in Kaupo). Spend the 25th (Wed) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: immerse yourself in nature at Wai'anapanapa State Park, pause for some photo ops at Fagan's Cross, kick back and relax at Red Sand Beach (Kaihalulu Beach), and tour the pleasant surroundings at Hamoa Beach.

For traveler tips, photos, more things to do, and more tourist information, read our Hana trip itinerary planner.

You can do a combination of bus and car from Lahaina to Hana in 2.5 hours. Alternatively, you can drive; or do a combination of bus and flight. In December in Hana, expect temperatures between 32°C during the day and 22°C at night. Finish your sightseeing early on the 9th (Thu) to allow enough time to 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
Wai'anapanapa State Park ©
Wai'anapanapa State Park

19
nights
Kailua

Kailua ©
Kailua is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Change things up with these side-trips from Kailua: Makapu’u Point Tide Pools (in Waimanalo), Hauula (Hauula Loop Trail & Kokololio Beach Park) and Haleiwa (Waimea Bay, Sunset Beach Park, & more). And it doesn't end there: kick back and relax at Kailua Beach Park, take a tour by water with Boat Tours & Water Sports, take in nature's colorful creations at Hoomaluhia Botanical Gardens, and get close to the beloved marine mammals with a swim-with-the-dolphins experience.

For photos, ratings, more things to do, and tourist information, you can read our Kailua online trip itinerary planner .

Traveling by flight from Hana to Kailua takes 4.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Hana in January, Kailua is a bit warmer at night with lows of 24°C. Wrap up your sightseeing by early afternoon on the 28th (Tue) to allow enough time to travel back home.

Things to do in Kailua

Parks Outdoors Beaches

Side Trips

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

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