8 days in Oahu, Kauai & Maui Itinerary

8 days in Oahu, Kauai & Maui Itinerary

Created using Inspirock Hawaii tour planner

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1
Honolulu
— 2 nights
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2
Kapaa
— 2 nights
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3
Kihei
— 3 nights
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Honolulu

— 2 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.
Get some cultural insight at USS Arizona Memorial and National Memorial Cemetery of the Pacific. You'll explore the less-touristy side of things at Lanikai Beach and Ko Olina Lagoons. Step out of Honolulu to go to Pupukea and see Sharks Cove, which is approximately 58 minutes away. There's more to do: trek along Koko Crater Railway Trail and discover the deep blue sea with a scuba or snorkeling tour.

To find where to stay, other places to visit, maps, and other tourist information, read our Honolulu planning site.

Chicago to Honolulu is an approximately 12-hour flight. The time zone changes from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST), which is usually a -4 hour difference. In December, Honolulu is much hotter than Chicago - with highs of 82°F and lows of 69°F. Cap off your sightseeing on the 18th (Fri) early enough to travel to Kapaa.

Things to do in Honolulu

Outdoors · Parks · Beaches · Historic Sites

Side Trips

Kapaa

— 2 nights
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Kick off your visit on the 19th (Sat): kick back and relax at Polihale State Park, then discover the deep blue sea with a scuba or snorkeling tour, and then admire the sheer force of Wailua Falls. Get ready for a full day of sightseeing on the 20th (Sun): hike along Kalalau Trail, then enjoy the sand and surf at Hanalei Beach, and then pause for some serene contemplation at Christ Memorial Episcopal Church.

For photos, other places to visit, traveler tips, and tourist information, you can read our Kapaa itinerary maker app.

You can fly from Honolulu to Kapaa in 4 hours. December in Kapaa sees daily highs of 79°F and lows of 67°F at night. Finish your sightseeing early on the 20th (Sun) so you can travel to Kihei.

Things to do in Kapaa

Parks · Outdoors · Wildlife · Beaches

Side Trips

Kihei

— 3 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.
On the 21st (Mon), kick back and relax at Ulua Beach, kick back and relax at Makena Beach, and then enjoy the sand and surf at Wailea Beach. Get ready for a full day of sightseeing on the next day: kick back and relax at Wailea Beach Path, tour the pleasant surroundings at Kamaole Beach Park II, then enjoy the sand and surf at Kamaole Beach Park III, and finally enjoy the sand and surf at Ho'okipa Beach Park.

To see other places to visit, reviews, and more tourist information, you can read our Kihei trip builder.

You can fly from Kapaa to Kihei in 4.5 hours. Expect a daytime high around 82°F in December, and nighttime lows around 66°F. Cap off your sightseeing on the 23rd (Wed) early enough to travel back home.

Things to do in Kihei

Beaches · Parks · Outdoors

Side Trips

Kauai travel guide

4.5
Scuba & Snorkeling · Zipline · Beaches
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Luaus
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.