18 days in Hawaii Itinerary

18 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner
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Lahaina, Maui
— 5 nights
Hilo, Island of Hawaii
— 2 nights
Kailua-Kona, Island of Hawaii
— 1 night
Fly to Lihue, Bus to Lawai Post Office, Shuttle to Poipu
Poipu, Kauai
— 2 nights
Shuttle to Lawai Post Office, Bus to Lihue, Fly to Honolulu
Honolulu, Oahu
— 7 nights


Lahaina, Maui — 5 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 Makawao (Maui Pineapple Tour & Maui Veterans Cemetery), Wailuku (Hale Ho'ike'ike at the Bailey House & Iao Valley) and Haleakala Crater (in Haleakala National Park). Spend the 22nd (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's lots more to do: see some colorful creatures with a scuba or snorkeling tour, test your problem-solving skills at Maui Escape Rooms, relax in the rural setting at Punakea Palms, and whizz through the canopy at some of the top local zipline courses and adventure parks.

To see more things to do, reviews, ratings, and tourist information, read Lahaina journey maker tool.

New York City to Lahaina is an approximately 12.5-hour flight. The time zone changes from Eastern Standard Time to Hawaii-Aleutian Standard Time, which is usually a -5 hour difference. Prepare for warmer weather when traveling from New York City in December: high temperatures in Lahaina hover around 78°F and lows are around 68°F. Finish up your sightseeing early on the 25th (Sun) so you can catch the flight to Hilo.
Outdoors · Parks · Scenic Drive · Tours
Side Trips
Find places to stay Dec 20 — 25:

Hilo, Island of Hawaii — 2 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.
Kick off your visit on the 26th (Mon): explore the different monuments and memorials at Alae Cemetery, cruise along Devastation Trail, then hike along Kilauea Iki Trailhead, and finally trek along Sulphur Banks. Get ready for a full day of sightseeing on the 27th (Tue): admire the sheer force of Rainbow Falls, learn something new at Hawaiian Crown Plantation & Chocolate Factory, then admire the natural beauty at Liliuokalani Gardens, then shop like a local with Hilo Farmers Market, and finally take in the dramatic scenery at Akaka Falls State Park.

To see photos, traveler tips, reviews, and other tourist information, read our Hilo online trip itinerary planner.

Fly from Lahaina to Hilo in 2.5 hours. December in Hilo sees daily highs of 80°F and lows of 65°F at night. Cap off your sightseeing on the 27th (Tue) early enough to go by car to Kailua-Kona.
Parks · Outdoors · Trails · Nature
Side Trip
Find places to stay Dec 25 — 27:

Kailua-Kona, Island of Hawaii — 1 night

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.
Kick off your visit on the 28th (Wed): experience rural life at Heavenly Hawaiian Kona Coffee Farm, then get close to the beloved marine mammals with a swim-with-the-dolphins experience, and then look for all kinds of wild species at Hawaii Forest and Trail.

To see maps, other places to visit, and tourist information, go to the Kailua-Kona attractions planning website.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In December, daytime highs in Kailua-Kona are 82°F, while nighttime lows are 70°F. Finish your sightseeing early on the 28th (Wed) to allow enough time to travel to Poipu.
Side Trip
Find places to stay Dec 27 — 28:

Poipu, Kauai — 2 nights

Start off your visit on the 29th (Thu): get interesting insight from Koloa Zipline, stroll through Waimea Canyon State Park, and then get a new perspective on things with Liko Kauai Cruises. Get ready for a full day of sightseeing on the 30th (Fri): stroll through Poipu Beach Park, see the world from above with a helicopter tour, and then see Kipu Ranch Adventures.

For reviews, other places to visit, more things to do, and other tourist information, use the Poipu trip itinerary planning tool.

Do a combination of flight, bus, and shuttle from Kailua-Kona to Poipu in 4.5 hours. In December, daily temperatures in Poipu can reach 79°F, while at night they dip to 67°F. Finish up your sightseeing early on the 30th (Fri) so you can travel to Honolulu.
Tours · Outdoors · Parks · Adventure
Side Trips
Find places to stay Dec 28 — 30:

Honolulu, Oahu — 7 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.
You'll find plenty of places to visit near Honolulu: Pupukea (Pu’u O Mahuka Heiau State Monument & Ehukai Beach Park), Kailua Beach Park (in Kailua) and Haleiwa (Waimea Bay & Sunset Beach Park). There's lots more to do: explore the different monuments and memorials at USS Arizona Memorial, explore the activities along Hanauma Bay Nature Preserve, take in the pleasant sights at Diamond Head State Monument, and take a memorable drive along Ihilani Spa.

To see more things to do, photos, other places to visit, and more tourist information, read Honolulu trip planner.

Traveling by combination of shuttle, bus, and flight from Poipu to Honolulu takes 4 hours. In December, daytime highs in Honolulu are 82°F, while nighttime lows are 69°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to fly back home.
Side Trips
Find places to stay Dec 30 — Jan 6:

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.

Kauai travel guide

Scuba & Snorkeling · Zipline · Beaches
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.