11 days in Hawaii Itinerary

11 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

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1
Honolulu, Oahu
— 4 nights
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2
Kailua-Kona, Island of Hawaii
— 1 night
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3
Lahaina, Maui
— 5 nights
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4
nights
Honolulu, Oahu

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.
Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Shark Diving, Sunset Beach Park, &more). Next up on the itinerary: kick back and relax at Waikiki Beach, explore the activities along Hanauma Bay Nature Preserve, stroll around Kapiolani Regional Park, and trek along Diamond Head State Monument.

Start your trip to Honolulu by creating a personalized itinerary on Inspirock.

Chicago to Honolulu is an approximately 12-hour flight. Traveling from Chicago to Honolulu, you'll gain 4 hours due to the time zone difference. Traveling from Chicago in August, you can expect nighttime temperatures to be a bit warmer in Honolulu, with lows of 75°F. Finish up your sightseeing early on the 9th (Mon) so you can travel to Kailua-Kona.

Things to do in Honolulu

Parks · Outdoors · Beaches · Nature

Side Trips

1
night
Kailua-Kona, Island of Hawaii

Heart of the Kona Coast

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.
On the 10th (Tue), experience rural life at Heavenly Hawaiian Kona Coffee Farm, tour the pleasant surroundings at Kahaluu Beach, then fulfill a lifelong dream with a swim-with-the-dolphins experience, and finally take a leisurely stroll along Kailua Pier.

To see where to stay, photos, more things to do, and other tourist information, go to the Kailua-Kona attractions planner.

You can fly from Honolulu to Kailua-Kona in 4 hours. August in Kailua-Kona sees daily highs of 87°F and lows of 77°F at night. Wrap up your sightseeing on the 10th (Tue) early enough to travel to Lahaina.

Things to do in Kailua-Kona

Outdoors · Wildlife · Tours · Parks

Side Trips

5
nights
Lahaina, Maui

Crown Jewel of 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.
Venture out of the city with trips to Haleakala Crater (in Haleakala National Park) and Iao Valley (in Wailuku). There's much more to do: see some colorful creatures with a scuba or snorkeling tour, admire nature's wide array of creatures at Maui Ocean Center, contemplate the geological forces at Molokini Crater, and stroll around Lahaina Banyan Court.

To see other places to visit, more things to do, photos, and tourist information, read Lahaina travel itinerary planner.

You can fly from Kailua-Kona to Lahaina in 4.5 hours. In August, daytime highs in Lahaina are 86°F, while nighttime lows are 74°F. Finish your sightseeing early on the 15th (Sun) to allow enough time to travel back home.

Things to do in Lahaina

Parks · Outdoors · Beaches · Nature

Side Trips

Hawaii travel guide

4.3
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.