27 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner
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Fly
1
Kailua-Kona, Island of Hawaii
— 4 nights
Drive
2
Hilo, Island of Hawaii
— 4 nights
Fly
3
Lahaina, Maui
— 7 nights
Fly
4
Lihue, Kauai
— 3 nights
Fly
5
Honolulu, Oahu
— 8 nights
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Kailua-Kona, Island of Hawaii — 4 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.
The Volcano Van Private Tours has been added to your itinerary. Change things up with these side-trips from Kailua-Kona: Puukohola National Historic Park (in Kawaihae), Hapuna Beach State Recreation Area (in Puako) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). The adventure continues: tour the pleasant surroundings at Mauna Kea Beach, get outside with Hawaii Offshore, take a stroll through Holualoa Village, and contemplate in the serene atmosphere at Mokuaikaua Church.

To find other places to visit, reviews, ratings, and tourist information, refer to the Kailua-Kona trip website.

Los Angeles to Kailua-Kona is an approximately 7.5-hour flight. The time zone difference when traveling from Los Angeles to Kailua-Kona is minus 2 hours. Expect somewhat warmer temperatures when traveling from Los Angeles in January; daily highs in Kailua-Kona reach 80°F and lows reach 67°F. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Hilo.
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Outdoors · Parks · Beaches · Nature
Side Trips
Find places to stay Jan 7 — 11:

Hilo, Island of Hawaii — 4 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Volcano Art Center Gallery, Devastation Trail, &more), Laupahoehoe Beach Park (in Laupahoehoe) and Steam Vents (in Pahoa). There's still lots to do: take in nature's colorful creations at Liliuokalani Gardens, take an unforgettable tour with a helicopter tour, take in the dramatic scenery at Rainbow Falls, and admire the majestic nature at Akaka Falls State Park.

To see other places to visit, where to stay, ratings, and tourist information, refer to the Hilo trip app.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. In January, plan for daily highs up to 81°F, and evening lows to 64°F. Cap off your sightseeing on the 15th (Sun) early enough to catch the flight to Lahaina.
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Parks · Outdoors · Trails · Nature
Side Trips
Find places to stay Jan 11 — 15:

Lahaina, Maui — 7 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.
Explore Lahaina's surroundings by going to Haleakala Crater (in Haleakala National Park), Kalepolepo Beach Park (in Kihei) and Maui Veterans Cemetery (in Makawao). Spend the 17th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: see some colorful creatures with a scuba or snorkeling tour, kick back and relax at Wailea Beach, walk around D.T. Fleming Park, and immerse yourself in nature at Iao Valley.

To see maps, where to stay, more things to do, and tourist information, you can read our Lahaina trip planner.

Traveling by flight from Hilo to Lahaina takes 2.5 hours. Expect a daytime high around 78°F in January, and nighttime lows around 67°F. Finish your sightseeing early on the 22nd (Sun) to allow enough time to fly to Lihue.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jan 15 — 22:

Lihue, Kauai — 3 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Change things up with these side-trips from Lihue: Hanalei Valley Lookout (in Princeville), Boat Tours & Water Sports (in Kekaha) and Na Pali Coast State Park (in Wainiha). The adventure continues: take in breathtaking views at Waimea Canyon State Park, take some stellar pictures from Puu Hinahina Lookout, kick back and relax at Tunnels Beach, and walk around Poipu Beach Park.

Plan a trip to Lihue easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by flight from Lahaina to Lihue takes 2.5 hours. Expect a daytime high around 79°F in January, and nighttime lows around 65°F. Wrap up your sightseeing on the 25th (Wed) to allow time to fly to Honolulu.
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Parks · Outdoors · Tours · Nature
Side Trips
Find places to stay Jan 22 — 25:

Honolulu, Oahu — 8 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.
Explore the numerous day-trip ideas around Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea) and Haleiwa (Sunset Beach Park & Waimea Bay). There's lots more to do: browse the exhibits of USS Arizona Memorial, go for a walk through Diamond Head State Monument, enjoy the sand and surf at Waikiki Beach, and contemplate the waterfront views at Hanauma Bay Nature Preserve.

To see traveler tips, ratings, maps, and other tourist information, use the Honolulu vacation maker.

Getting from Lihue to Honolulu by flight takes about 2.5 hours. January in Honolulu sees daily highs of 81°F and lows of 67°F at night. Cap off your sightseeing on the 2nd (Thu) early enough to catch the flight back home.
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Parks · Outdoors · Beaches · Museums
Side Trips
Find places to stay Jan 25 — Feb 2:

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.
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