16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii itinerary planner
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Lahaina, Maui
— 3 nights
Kailua-Kona, Island of Hawaii
— 2 nights
Lihue, Kauai
— 2 nights
Honolulu, Oahu
— 8 nights


Lahaina, Maui — 3 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.
Satisfy your inner culture vulture at Haiku Mill and Native Intelligence. You'll explore the less-touristy side of things at Zipline and Kamaole Beach Park II. You'll find plenty of places to visit near Lahaina: Ho'okipa Beach Park (in Paia), Wailea Beach (in Wailea) and Kamaole Beach Park III (in Kihei). There's much more to do: head outdoors with Outdoor Activities, kick back and relax at Kapalua Beach, stroll around D.T. Fleming Park, and stroll through Napili Beach.

Plan a Lahaina trip in moments using our itinerary builder.

Chicago to Lahaina is an approximately 11-hour flight. The time zone changes from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST), which is usually a -4 hour difference. Prepare for warmer weather when traveling from Chicago in February: high temperatures in Lahaina hover around 30°C and lows are around 22°C. Finish your sightseeing early on the 17th (Thu) to allow enough time to fly to Kailua-Kona.
Outdoors · Parks · Beaches · Tours
Side Trips

Kailua-Kona, Island of Hawaii — 2 nights

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.
Kick off your visit on the 18th (Fri): tour the pleasant surroundings at Pu'uhonua O Honaunau National Historical Park, contemplate the waterfront views at Kealakekua Bay, and then get close to the beloved marine mammals with a swim-with-the-dolphins experience. On your second day here, tour the pleasant surroundings at Manini'owali Beach (Kua Bay), then admire all the interesting features of Puako Petroglyph Archaeological Preserve, and then stroll through Hapuna Beach State Recreation Area.

To find more things to do, traveler tips, where to stay, and more tourist information, read our Kailua-Kona online visit planner.

Traveling by flight from Lahaina to Kailua-Kona takes 2.5 hours. In February, daily temperatures in Kailua-Kona can reach 32°C, while at night they dip to 24°C. Wrap up your sightseeing on the 19th (Sat) early enough to fly to Lihue.
Parks · Outdoors · Nature · Beaches
Side Trips

Lihue, Kauai — 2 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Start off your visit on the 20th (Sun): explore the striking landscape at Spouting Horn, hike along Maha'ulepu Heritage Trail, then discover the deep blue sea with a scuba or snorkeling tour, and finally admire the sheer force of Wailua Falls. Here are some ideas for day two: admire the sheer force of Opaekaa Falls, tour the pleasant surroundings at Kilauea Point National Wildlife Refuge, then kick back and relax at Hanalei Beach, and finally take some stellar pictures from Hanalei Valley Lookout.

To see ratings, where to stay, photos, and other tourist information, you can read our Lihue trip builder.

You can fly from Kailua-Kona to Lihue in 2.5 hours. Expect a daytime high around 30°C in February, and nighttime lows around 22°C. Cap off your sightseeing on the 21st (Mon) early enough to catch the flight to Honolulu.
Parks · Outdoors · Wildlife · Nature
Side Trips

Honolulu, Oahu — 8 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Escape the urban bustle at Makapuu Lighthouse Trail and Kailua Beach Park. Satisfy your inner culture vulture at USS Arizona Memorial and National Memorial Cemetery of the Pacific. You'll find plenty of places to visit near Honolulu: Byodo-In Temple (in Kaneohe), Haleiwa (Waimea Valley & Sunset Beach Park) and Shark's Cove (in Pupukea). There's still lots to do: meet some fierce fish with a shark diving experience, enjoy the sand and surf at Waikiki Beach, admire the sheer force of Manoa Falls, and go for a walk through Diamond Head State Monument.

To find where to stay, maps, photos, and other tourist information, refer to the Honolulu vacation planner.

You can fly from Lihue to Honolulu in 2.5 hours. In February, plan for daily highs up to 32°C, and evening lows to 24°C. Wrap up your sightseeing on the 1st (Tue) early enough to fly back home.
Outdoors · Parks · Beaches · Historic Sites
Side Trips

Hawaii travel guide

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.