17 days in Hawaii Itinerary

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Honolulu, Oahu
— 6 nights
Lahaina, Maui
— 4 nights
Kailua-Kona, Island of Hawaii
— 2 nights
Lihue, Kauai
— 3 nights


Honolulu, Oahu — 6 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.
Satisfy your inner culture vulture at USS Arizona Memorial and USS Bowfin Submarine Museum & Park. Visiting Diamond Head State Monument and Swim with Dolphins will get you outdoors. Explore Honolulu's surroundings by going to Haleiwa (Shark Diving & Sunset Beach Park), Kailua (Kailua Beach Park & Lanikai Beach) and North Shore Goodies (in Waialua). There's lots more to do: stroll through Waikiki Beach, contemplate the waterfront views at Hanauma Bay Nature Preserve, step aboard Battleship Missouri Memorial, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

Planning Honolulu trip won't be overwhelming when you use Inspirock's itinerary maker.

Boston to Honolulu is an approximately 11-hour flight. The time zone changes from Eastern Standard Time to Hawaii-Aleutian Standard Time, which is usually a -5 hour difference. Traveling from Boston in January, expect Honolulu to be warmer, temps between 32°C and 22°C. Wrap up your sightseeing on the 9th (Mon) early enough to fly to Lahaina.
Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Jan 3 — 9:

Lahaina, Maui — 4 nights

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.
We've included these beaches for you: Ka'anapali Beach and Ho'okipa Beach Park. Get outdoors at Haleakala Crater and Kalepolepo Beach Park. Take a break from Lahaina with a short trip to Wailea Beach in Wailea, about 46 minutes away. There's lots more to do: take a memorable drive along Hana Highway - Road to Hana, walk around Lahaina Banyan Court, and stroll through Kapalua Beach.

To see ratings and more tourist information, read Lahaina trip planner.

Traveling by flight from Honolulu to Lahaina takes 2.5 hours. January in Lahaina sees daily highs of 30°C and lows of 22°C at night. Wrap up your sightseeing on the 13th (Fri) early enough to fly to Kailua-Kona.
Outdoors · Parks · Beaches · Scenic Drive
Side Trips
Find places to stay Jan 9 — 13:

Kailua-Kona, Island of Hawaii — 2 nights

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.
Start off your visit on the 14th (Sat): get engrossed in the history at H.N. Greenwell Store Museum, tour the pleasant surroundings at Pu'uhonua O Honaunau National Historical Park, then explore the galleries of Kona Coffee Living History Farm, and finally fulfill a lifelong dream with a swim-with-the-dolphins experience. Keep things going the next day: enjoy the sand and surf at Mauna Kea Beach and then stroll through Hapuna Beach State Recreation Area.

For more things to do, other places to visit, where to stay, and tourist information, you can read our Kailua-Kona tour itinerary maker.

Fly from Lahaina to Kailua-Kona in 2.5 hours. In January, daily temperatures in Kailua-Kona can reach 31°C, while at night they dip to 22°C. Finish your sightseeing early on the 15th (Sun) to allow enough time to fly to Lihue.
Outdoors · Parks · Beaches · Nature
Side Trips
Find places to stay Jan 13 — 15:

Lihue, Kauai — 3 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Escape the urban bustle at Na Pali Coast State Park and Hanalei Beach. You'll get in some beach time at Poipu Beach Park and Tunnels Beach. Explore Lihue's surroundings by going to Waimea Canyon State Park (in Waimea) and Kekaha (Kokee Natural History Museum & Scuba & Snorkeling). There's more to do: explore the striking landscape at Spouting Horn and take in the dramatic scenery at Opaekaa Falls.

To find where to stay, photos, ratings, and other tourist information, refer to the Lihue trip planner.

Getting from Kailua-Kona to Lihue by flight takes about 2.5 hours. In January, daily temperatures in Lihue can reach 30°C, while at night they dip to 21°C. Finish up your sightseeing early on the 18th (Wed) so you can catch the flight back home.
Parks · Outdoors · Beaches · Wildlife
Side Trips
Find places to stay Jan 15 — 18:

Hawaii travel guide

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.