15 days in Hawaii Itinerary

15 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route planner

This plan was created by another user. Make it your plan

Route & dates

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

3
nights
Kihei, Maui

Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Change things up with these side-trips from Kihei: Lahaina (Lahaina Banyan Court & Scuba & Snorkeling), Ho'okipa Beach Park (in Paia) and Haleakala Crater (in Haleakala National Park). There's lots more to do: take a memorable drive along Hana Highway - Road to Hana, enjoy the sand and surf at Kalepolepo Beach Park, take in the architecture and atmosphere at The Awakening Church, and admire all the interesting features of Haleakala Highway (Crater Road).

To see ratings, photos, other places to visit, and other tourist information, refer to the Kihei trip builder.

Chicago to Kihei is an approximately 11- hour flight. The time zone difference when traveling from Chicago to Kihei is minus 4 hours. Plan for much warmer temperatures traveling from Chicago in April, with highs in Kihei at 85°F and lows at 68°F. Finish up your sightseeing early on the 7th (Tue) so you can travel to Hilo.

Things to do in Kihei

Outdoors Parks Scenic Drive

Side Trips

Lahaina, Maui, Maui Ocean Center, Story of Hawaii Museum, Ho'okipa Beach Park
Highlights from your plan
Scuba & Snorkeling
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

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.
On the 8th (Wed), explore the striking landscape at Thurston Lava Tube (Nahuku), hike along Kilauea Iki Trailhead, then hike along Kipuka Puaulu (Bird Park) Trail, and finally examine the collection at Jagger Museum. Keep things going the next day: take in the dramatic scenery at Rainbow Falls, learn more about the world around you at Mokupapapa Discovery Center, admire the natural beauty at Liliuokalani Gardens, then admire the natural beauty at Hawaii Tropical Botanical Garden, and finally admire the sheer force of Akaka Falls State Park.

To find where to stay, traveler tips, and tourist information, read Hilo sightseeing tool.

Do a combination of bus and flight from Kihei to Hilo in 3 hours. Alternatively, you can do a combination of bus and flight. April in Hilo sees daily highs of 81°F and lows of 67°F at night. Finish your sightseeing early on the 9th (Thu) so you can drive to Kailua-Kona.

Things to do in Hilo

Parks Nature Trails

Side Trips

Hawaii Volcanoes National Park, Hawaii Tropical Botanical Garden, Jagger Museum
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

3
nights
Kailua-Kona, Island of Hawaii

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.
Explore Kailua-Kona's surroundings by going to Puukohola National Historic Park (in Kawaihae), Hapuna Beach State Recreation Area (in Puako) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). There's lots more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, enjoy the sand and surf at Kahaluu Beach, stroll through Mauna Kea Beach, and tee off at Mauna Lani Resort .

For reviews, other places to visit, where to stay, and other tourist information, you can read our Kailua-Kona online tour builder.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. April in Kailua-Kona sees daily highs of 83°F and lows of 72°F at night. Finish your sightseeing early on the 12th (Sun) to allow enough time to travel to Honolulu.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Island of Hawaii, Puukohola National Historic Park, Hapuna Beach State Recreation Area, Pu'uhonua O Honaunau National Historical Park, Kona Coffee Living History Farm
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Pu'uhonua O Honaunau National Historical Park ©
Pu'uhonua O Honaunau National Historical Park

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.
Venture out of the city with trips to Haleiwa (Sunset Beach Park & Waimea Bay), Waianae (Mermaid Caves & Swim with Dolphins) and Kailua Beach Park (in Kailua). The adventure continues: go for a walk through Diamond Head State Monument, contemplate the long history of Battleship Missouri Memorial, take an in-depth tour of Iolani Palace, and admire the sheer force of Manoa Falls.

For traveler tips, reviews, and tourist information, go to the Honolulu online attractions planner.

Getting from Kailua-Kona to Honolulu by combination of bus and flight takes about 4 hours. Other options: fly. In April in Honolulu, expect temperatures between 83°F during the day and 71°F at night. Wrap up your sightseeing on the 18th (Sat) early enough to travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Waianae, Halona Blowhole, 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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