13 days in Honolulu, Island of Hawaii & Maui Itinerary

13 days in Honolulu, Island of Hawaii & Maui Itinerary

Created using Inspirock Hawaii journey planner

Make it your trip
Fly
1
Honolulu
— 5 nights
Fly
2
Hilo
— 2 nights
Drive
3
Kailua-Kona
— 1 night
Fly
4
Lahaina
— 4 nights
Fly

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Honolulu

— 5 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.
Get out of town with these interesting Honolulu side-trips: Haleiwa (Sunset Beach Park & Waimea Bay), Ehukai Beach Park (in Pupukea) and Kailua Beach Park (in Kailua). And it doesn't end there: stroll the grounds of USS Arizona Memorial, browse the different shops at Ala Moana Center, steep yourself in history at Iolani Palace, and appreciate the history behind King Kamehameha Statue.

To see maps, where to stay, other places to visit, and more tourist information, read our Honolulu route tool.

Chicago to Honolulu is an approximately 12-hour flight. Due to the time zone difference, you'll gain 4 hours traveling from Chicago to Honolulu. Plan for warmer temperatures traveling from Chicago in December, with highs in Honolulu at 82°F and lows at 69°F. Wrap up your sightseeing on the 29th (Wed) early enough to travel to Hilo.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Hilo

— 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.
Start off your visit on the 30th (Thu): see the interesting displays at Jagger Museum, trek along Kipuka Puaulu (Bird Park) Trail, then stroll through Kilauea Iki Trailhead, and finally tour the pleasant surroundings at Sulphur Banks. On the next day, take in the dramatic scenery at Rainbow Falls, take in the dramatic scenery at Akaka Falls State Park, stop by Basically Books, then take in nature's colorful creations at Liliuokalani Gardens, and finally see the world from above with a helicopter tour.

To see photos, reviews, ratings, and tourist information, read Hilo trip itinerary site.

You can fly from Honolulu to Hilo in 3.5 hours. Expect a daytime high around 80°F in December, and nighttime lows around 65°F. Finish up your sightseeing early on the 31st (Fri) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Trails · Nature

Side Trips

Kailua-Kona

— 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.
On the 1st (Sat), relax in the rural setting at Heavenly Hawaiian Kona Coffee Farm, then kick back and relax at Kahaluu Beach, then fulfill a lifelong dream with a swim-with-the-dolphins experience, and finally take in the spiritual surroundings of Mokuaikaua Church.

For maps, traveler tips, reviews, and tourist information, go to the Kailua-Kona tour itinerary planner.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. In December, plan for daily highs up to 82°F, and evening lows to 70°F. Finish up your sightseeing early on the 1st (Sat) so you can travel to Lahaina.

Things to do in Kailua-Kona

Outdoors · Wildlife · Tours · Beaches

Side Trips

Lahaina

— 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.
Step out of Lahaina to go to Wailuku and see Iao Valley, which is approximately 44 minutes away. Spend the 3rd (Mon) 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, take a memorable tour with Tours, relax in the rural setting at Punakea Palms, and walk around Lahaina Banyan Court.

Before you visit Lahaina, use our trip planner to discover what you can do and see there.

Fly from Kailua-Kona to Lahaina in 4.5 hours. In January, daily temperatures in Lahaina can reach 78°F, while at night they dip to 67°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to travel back home.

Things to do in Lahaina

Outdoors · Parks · Scenic Drive · Tours

Side Trips

Island of Hawaii travel guide

4.5
Swim with Dolphins · Scuba & Snorkeling · Beaches
The Big Island
Aptly nicknamed the "Big Island," the Island of Hawaii features sunny, black-sand beaches on the western side by Kona and a tropical rain forest on the eastern by Hilo. In between, the massive mountain Maunaloa covers half the island, and Kilauea, one of the world's most active volcanoes, erupts continuously. Twice as large as all the other Hawaiian Islands combined, this big chunk of land in the Pacific manages to retain a laid-back atmosphere despite its immense popularity with tourists. Instead of spending your entire vacation at one of the island's luxurious tourist resorts, go on tours of this Pacific haven's coffee and macadamia nut plantations and working ranches, or explore its nature reserves and rugged trails.

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Luaus
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.