14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
Make it your trip
Fly
1
Honolulu, Oahu
— 6 nights
Fly
2
Koloa, Kauai
— 3 nights
Fly
3
Lahaina, Maui
— 4 nights
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Honolulu, Oahu — 6 nights

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 visit kid-friendly attractions like USS Arizona Memorial and Hanauma Bay Nature Preserve. Explore the numerous day-trip ideas around Honolulu: Haleiwa (Sunset Beach Park & Waimea Bay), Turtle Bay Beach (in Kahuku) and Kailua Beach Park (in Kailua). Next up on the itinerary: enjoy the sand and surf at Waikiki Beach, take in the dramatic scenery at Manoa Falls, buy something for everyone on your list at Ala Moana Center, and work some fitness into your day at Ala Moana Beach Park.

For other places to visit, reviews, photos, and other tourist information, use the Honolulu journey tool.

Chicago to Honolulu is an approximately 11-hour flight. You'll gain 4 hours traveling from Chicago to Honolulu due to the time zone difference. Traveling from Chicago in January, expect Honolulu to be much warmer, temps between 81°F and 67°F. Finish your sightseeing early on the 25th (Tue) so you can fly to Koloa.
Parks · Outdoors · Beaches · Museums
Side Trips

Koloa, Kauai — 3 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Attractions like Waimea Canyon State Park and Hanalei Beach make great kid-friendly stops. Change things up with these side-trips from Koloa: Hanalei Valley Lookout (in Hanalei) and Na Pali Coast State Park (in Wainiha). There's still lots to do: stroll around Poipu Beach Park, explore the striking landscape at Spouting Horn, steep yourself in history at Prince Kuhio Park, and tour the pleasant surroundings at Shipwreck Beach.

For traveler tips, other places to visit, more things to do, and tourist information, read our Koloa driving holiday planning tool.

You can fly from Honolulu to Koloa in 2.5 hours. Alternatively, you can fly. January in Koloa sees daily highs of 79°F and lows of 65°F at night. Wrap up your sightseeing on the 28th (Fri) to allow time to fly to Lahaina.
Parks · Outdoors · Beaches · Nature
Side Trips

Lahaina, Maui — 4 nights

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.
Family-friendly places like Scuba & Snorkeling and Iao Valley will thrill your kids. When in Lahaina, make a side trip to see Hale Ho'ike'ike at the Bailey House in Wailuku, approximately Wailuku away. Spend the 29th (Sat) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: observe the fascinating underwater world at Maui Ocean Center, stroll through Napili Beach, stroll around Lahaina Banyan Court, and pause for some photo ops at Lahaina Jodo Mission.

To see maps, traveler tips, and tourist information, read Lahaina trip itinerary planner.

Fly from Koloa to Lahaina in 2.5 hours. In January in Lahaina, expect temperatures between 78°F during the day and 67°F at night. Finish your sightseeing early on the 1st (Tue) to allow enough time to fly back home.
Outdoors · Parks · Scenic Drive · Beaches
Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.