36 days in Orlando, New York City & Hawaii Itinerary

36 days in Orlando, New York City & Hawaii Itinerary

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Route & dates

36 days in Orlando, New York City & Hawaii Itinerary

Start: Sydney
Fly:  25​h
1
Orlando
— 8 nights
Fly:  6​h
2
New York City
— 6 nights
Bus + Fly:  13​h 45​min
3
Honolulu, Oahu
— 4 nights
Fly + Taxi:  3​h
4
Hanalei, Kauai
— 2 nights
Drive:  1​h 30​min
5
Waimea, Kauai
— 1 night
Fly + Bus:  4​h
6
Lahaina, Maui
— 5 nights
Fly:  4​h
7
Kailua-Kona, Island of Hawaii
— 4 nights
Drive:  1​h 45​min
8
Hilo, Island of Hawaii
— 2 nights
Fly:  13​h
End: Sydney

8
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Explore hidden gems such as Stetson Mansion and Disney's Typhoon Lagoon Water Park. Get out of town with these interesting Orlando side-trips: Crystal River (Stand-Up Paddleboarding & Scuba & Snorkeling). Pack the 4th (Wed) with family-friendly diversions at Universal's Islands of Adventure. Have a day of magic on the 5th (Thu) at Walt Disney World Resort. And it doesn't end there: test your team's savvy at The Escape Game Orlando, enjoy unforgettable views with a balloon tour, discover the magic at Happily Ever After Fireworks, and stop by The LEGO Store Downtown Disney.

To see photos and tourist information, go to the Orlando road trip planner .

Sydney, Australia to Orlando is an approximately 25-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. The time zone changes from Australian Eastern Standard Time (New South Wales) to Eastern Standard Time, which is usually a -15 hour difference. Traveling from Sydney in December, expect a bit cooler with lows of 17°C in Orlando. Wrap up your sightseeing on the 9th (Mon) early enough to travel to New York City.

Things to do in Orlando

Theme Parks Tours Outdoors

Side Trips

Crystal River, Charles Hosmer Morse Museum of American Art, Stetson Mansion
Find places to stay Dec 1 — 9:
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
The Escape Game Orlando ©
The Escape Game Orlando
Avatar Flight of Passage ©
Avatar Flight of Passage

6
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Discover out-of-the-way places like Food Tours and Photography Tours. The adventure continues: take in the pleasant sights at Central Park, take in the architecture and atmosphere at St. Patrick's Cathedral, take in panoramic vistas at Top of the Rock, and pause for some photo ops at Statue of Liberty National Monument.

For photos, where to stay, and other tourist information, read New York City trip itinerary website .

Fly from Orlando to New York City in 6 hours. Alternatively, you can do a combination of flight and bus; or drive. In December, New York City is cooler than Orlando - with highs of 10°C and lows of 2°C. Cap off your sightseeing on the 16th (Mon) early enough to travel to Honolulu.

Things to do in New York City

Museums Parks Historic Sites

Side Trip

Brooklyn Heights Promenade
Find places to stay Dec 9 — 16:
Highlights from your plan
Central Park ©
Central Park
Food Tours
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

4
nights
Honolulu, Oahu

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 discover tucked-away gems like Koko Crater Railway Trail and Battleship Missouri Memorial. Step out of Honolulu to go to Laie and see Polynesian Cultural Center, which is approximately 1h 05 min away. Next up on the itinerary: discover the deep blue sea with a scuba or snorkeling tour, see the interesting displays at Iolani Palace, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, and tour the pleasant surroundings at Waikiki Beach.

To find ratings, traveler tips, more things to do, and more tourist information, go to the Honolulu day trip planner .

You can do a combination of bus and flight from New York City to Honolulu in 14 hours. Another option is to fly. The time zone changes from Eastern Standard Time (EST) to Hawaii Standard Time (HST), which is usually a -5 hour difference. Plan for much warmer temperatures traveling from New York City in December, with highs in Honolulu at 32°C and lows at 24°C. Finish up your sightseeing early on the 21st (Sat) so you can travel to Hanalei.

Things to do in Honolulu

Outdoors Parks Historic Sites

Side Trip

Polynesian Cultural Center
Find places to stay Dec 16 — 21:
Highlights from your plan
Scuba & Snorkeling
Koko Crater Railway Trail ©
Koko Crater Railway Trail
Battleship Missouri Memorial ©
Battleship Missouri Memorial

2
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. On the 22nd (Sun), admire the sheer force of Wailua Falls and then paddle through the water with a kayaking and canoeing tour. On the 23rd (Mon), you'll have a packed day of sightseeing: hike along Kalalau Trail and then admire the majestic nature at Na Pali Coast State Park.

For photos, reviews, where to stay, and more tourist information, read Hanalei online trip planner .

You can do a combination of flight and taxi from Honolulu to Hanalei in 3 hours. In December, plan for daily highs up to 30°C, and evening lows to 22°C. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Waimea.

Things to do in Hanalei

Parks Outdoors Wildlife

Side Trips

Wailua Falls, Kayaking & Canoeing, Kalalau Trail, Na Pali Coast State Park
Find places to stay Dec 21 — 23:
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Kayaking & Canoeing
Wailua Falls ©
Wailua Falls

1
night
Waimea, Kauai

Waimea ©
Start off your visit on the 24th (Tue): get up close to creatures of the deep with a dolphin and whale watching tour and then take in breathtaking views at Waimea Canyon State Park.

To see reviews, ratings, photos, and more tourist information, use the Waimea route site .

Traveling by car from Hanalei to Waimea takes 1.5 hours. In December in Waimea, expect temperatures between 30°C during the day and 22°C at night. Finish your sightseeing early on the 24th (Tue) to allow enough time to travel to Lahaina.

Things to do in Waimea

Nature Parks
Find places to stay Dec 23 — 24:
Highlights from your plan
Waimea Canyon State Park ©
Waimea Canyon State Park

5
nights
Lahaina, Maui

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 hidden gems such as Zipline and Lahaina Front Street. Explore the numerous day-trip ideas around Lahaina: Kihei (Maui Brewing Company, Stand-Up Paddleboarding, & more), Haleakala Crater (in Haleakala National Park) and Helicopter Tours (in Kahului). There's still lots to do: get interesting insight from Tours, observe the fascinating underwater world at Maui Ocean Center, don't miss a visit to Lahaina Banyan Court, and kick back and relax at Napili Beach.

To see where to stay, maps, more things to do, and tourist information, read our Lahaina trip itinerary maker .

You can do a combination of flight and bus from Waimea to Lahaina in 4 hours. Another option is to fly. In December, daily temperatures in Lahaina can reach 30°C, while at night they dip to 23°C. Finish your sightseeing early on the 29th (Sun) so you can travel to Kailua-Kona.

Things to do in Lahaina

Outdoors Parks Tours

Side Trips

Kihei, Maui Ocean Center, Haleakala Crater, Helicopter Tours, Wailea Beach
Find places to stay Dec 24 — 29:
Highlights from your plan
Dolphin & Whale Watching
Scuba & Snorkeling
Haleakala Crater ©
Haleakala Crater

4
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.
Eschew the tourist crowds and head to Scuba & Snorkeling and Mauna Kea. Explore the numerous day-trip ideas around Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Hapuna Beach State Recreation Area (in Puako). There's much more to do: see majestic marine mammals with a dolphin and whale watching tour, explore and take pictures at Mountain Thunder Coffee Plantation, make a trip to Saddle Road, and cast your line with a fishing tour.

To see other places to visit, traveler tips, maps, and other tourist information, use the Kailua-Kona planning app .

Traveling by flight from Lahaina to Kailua-Kona takes 4 hours. Alternatively, you can do a combination of bus, flight, and taxi; or do a combination of bus and flight. Expect a daytime high around 32°C in December, and nighttime lows around 24°C. Finish your sightseeing early on the 2nd (Thu) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Outdoors Tours Wildlife

Side Trips

Pu'uhonua O Honaunau National Historical Park, Greenwell Farms, Hapuna Beach State Recreation Area
Find places to stay Dec 29 — Jan 2:
Highlights from your plan
Dolphin & Whale Watching
Greenwell Farms ©
Greenwell Farms
Hapuna Beach State Recreation Area ©

2
nights
Hilo, Island of Hawaii

Hilo ©
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.
On the 3rd (Fri), admire the sheer force of Rainbow Falls, see the interesting displays at Jagger Museum, take an unforgettable tour with a helicopter tour, then take in nature's colorful creations at Liliuokalani Gardens, and finally admire the sheer force of Akaka Falls State Park.

For maps, where to stay, and other tourist information, read Hilo trip website .

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. In January, daytime highs in Hilo are 32°C, while nighttime lows are 20°C. Wrap up your sightseeing by early afternoon on the 4th (Sat) to allow time for travel back home.

Things to do in Hilo

Parks Tours Nature

Side Trips

Hawaii Tropical Botanical Garden, Jagger Museum
Find places to stay Jan 2 — 4:
Highlights from your plan
Akaka Falls State Park ©
Akaka Falls State Park
Helicopter Tours
Jagger Museum ©
Jagger Museum

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