15 days in Hawaii Itinerary

15 days in Hawaii Itinerary

Created using Inspirock Hawaii vacation maker

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Route & dates

Start: Chicago
Fly:  13 h
1
Hilo, Island of Hawaii
— 2 nights
Drive:  1 h 45 min
2
Kailua-Kona, Island of Hawaii
— 2 nights
Bus + Fly:  4 h
3
Lahaina, Maui
— 4 nights
Fly:  3 h 15 min
4
Honolulu, Oahu
— 6 nights
Fly:  11 h 30 min
End: Chicago

2
nights
Hilo, Island of Hawaii

Hilo ©
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 2nd (Thu): take a memorable drive along Devastation Trail, then hike along Kilauea Iki Trailhead, then admire the natural beauty at Liliuokalani Gardens, and finally immerse yourself in nature at Akaka Falls State Park. Keep things going the next day: stop by Hilo Coffee Mill, examine the collection at Jagger Museum, hike along Kipuka Puaulu (Bird Park) Trail, then get impressive views of Kīlauea, and finally head outdoors with Keanakakoi Crater Overlook.

To find photos, where to stay, maps, and other tourist information, read Hilo attractions site.

Chicago to Hilo is an approximately 13- hour flight. You can also do a combination of flight and bus. The time zone difference moving from Central Standard Time (CST) to Hawaii Standard Time (HST) is minus 4 hours. Traveling from Chicago in April, expect Hilo to be much hotter, temps between 81°F and 67°F. Finish your sightseeing early on the 3rd (Fri) so you can drive to Kailua-Kona.

Things to do in Hilo

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Jagger Museum, Hilo Coffee Mill
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Akaka Falls State Park ©
Akaka Falls State Park
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

2
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
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 4th (Sat): look for gifts at 2nd Wave Beach and Boat, steep yourself in history at Pu'uhonua O Honaunau National Historical Park, then enjoy the sand and surf at Kahaluu Beach, and finally get close to the beloved marine mammals with a swim-with-the-dolphins experience. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Puako Petroglyph Archaeological Preserve, then explore the striking landscape of Puukohola National Historic Park, and then kick back and relax at Hapuna Beach State Recreation Area.

To find maps, photos, and more tourist information, go to the Kailua-Kona tour itinerary planning app.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. Expect a daytime high around 83°F in April, and nighttime lows around 72°F. Finish your sightseeing early on the 5th (Sun) so you can travel to Lahaina.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Puukohola National Historic Park, Hapuna Beach State Recreation Area, Pu'uhonua O Honaunau National Historical Park, Puako Petroglyph Archaeological Preserve, Kahaluu Beach
Highlights from your plan
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Swim with Dolphins
Pu'uhonua O Honaunau National Historical Park ©

4
nights
Lahaina, 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.
You'll visit kid-friendly attractions like Iao Valley and Napili Beach. Explore the numerous day-trip ideas around Lahaina: Kula Country Farms (in Kula), Laura Mango Art Gallery (in Hana) and Haleakala Crater (in Haleakala National Park). There's lots more to do: see some colorful creatures with a scuba or snorkeling tour, enjoy the sand and surf at Kapalua Beach, observe the fascinating underwater world at Maui Ocean Center, and appreciate the history behind Lahaina Jodo Mission.

For maps, reviews, where to stay, and tourist information, go to the Lahaina day trip planning site.

Getting from Kailua-Kona to Lahaina by combination of bus and flight takes about 4 hours. Other options: do a combination of taxi, flight, and bus; or do a combination of bus and flight. In April, daytime highs in Lahaina are 80°F, while nighttime lows are 69°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to travel to Honolulu.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailuku, Kula Country Farms, Laura Mango Art Gallery, Kapalua Beach, Haleakala Crater
Highlights from your plan
Scuba & Snorkeling
Haleakala Crater ©
Haleakala Crater
Maui Ocean Center ©
Maui Ocean Center

6
nights
Honolulu, Oahu

Honolulu ©
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 visit kid-friendly attractions like Diamond Head State Monument and Hanauma Bay Nature Preserve. Venture out of the city with trips to Haleiwa (Waimea Bay, Sunset Beach Park, &more), Swim with Dolphins (in Waianae) and Kailua Beach Park (in Kailua). And it doesn't end there: admire the sheer force of Manoa Falls, enjoy the sand and surf at Waikiki Beach, pause for some photo ops at Queen Liliuokalani Statue, and explore the different monuments and memorials at USS Arizona Memorial.

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

You can fly from Lahaina to Honolulu in 3.5 hours. Alternatively, you can do a combination of ferry and flight; or do a combination of bus and flight. Expect a daytime high around 83°F in April, and nighttime lows around 71°F. Wrap up your sightseeing on the 15th (Wed) to allow time to travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Swim with Dolphins, Kailua Beach Park
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
USS Arizona Memorial ©
USS Arizona Memorial

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