15 days in Hawaii Itinerary

15 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

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Route & dates

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

2
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.
Kick off your visit on the 22nd (Sun): contemplate the long history of Pu'uhonua O Honaunau National Historical Park, fulfill a lifelong dream with a swim-with-the-dolphins experience, and then take in the spiritual surroundings of Mokuaikaua Church. Get ready for a full day of sightseeing on the 23rd (Mon): enjoy the sand and surf at Mauna Kea Beach and then enjoy the sand and surf at Hapuna Beach State Recreation Area.

Plan a Kailua-Kona trip in moments using our itinerary builder.

Toronto, Canada to Kailua-Kona is an approximately 16.5-hour flight. The time zone difference when traveling from Toronto to Kailua-Kona is minus 5 hours. Traveling from Toronto in December, expect Kailua-Kona to be much hotter, temps between 32°C and 24°C. Cap off your sightseeing on the 23rd (Mon) early enough to go by car to Hilo.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Pu'uhonua O Honaunau National Historical Park, Hapuna Beach State Recreation Area, Mauna Kea Beach
Find places to stay Dec 21 — 23:
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Pu'uhonua O Honaunau National Historical Park ©

3
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.
Venture out of the city with trips to Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Sulphur Banks, &more). There's still lots to do: admire the sheer force of Akaka Falls State Park and admire the natural beauty at Liliuokalani Gardens.

To see ratings, where to stay, other places to visit, and tourist information, read our Hilo trip itinerary planner.

Drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in December, plan for slightly colder nights in Hilo, with lows around 21°C. Finish your sightseeing early on the 26th (Thu) so you can travel to Kihei.

Things to do in Hilo

Outdoors Parks Trails

Side Trip

Hawaii Volcanoes National Park
Find places to stay Dec 23 — 26:
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
Kihei, Maui

Kihei ©
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.
You'll find plenty of places to visit near Kihei: Lahaina (Lahaina Banyan Court & Ka'anapali Beach), Haleakala Crater (in Haleakala National Park) and Ho'okipa Beach Park (in Paia). Next up on the itinerary: cruise along Hana Highway - Road to Hana, enjoy the sand and surf at Kalepolepo Beach Park, observe the fascinating underwater world at Maui Ocean Center, and take in the architecture and atmosphere at The Awakening Church.

To see maps, other places to visit, traveler tips, and other tourist information, read our Kihei driving holiday planner.

You can fly from Hilo to Kihei in 3 hours. In December, daytime highs in Kihei are 32°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 29th (Sun) so you can travel to Honolulu.

Things to do in Kihei

Parks Outdoors Beaches

Side Trips

Lahaina, Haleakala Crater, Ho'okipa Beach Park, Maui Ocean Center, Hana Highway - Road to Hana
Find places to stay Dec 26 — 29:
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
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.
Explore the numerous day-trip ideas around Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Sunset Beach Park & Waimea Bay). The adventure continues: explore the different monuments and memorials at USS Arizona Memorial, hit the best photo ops around with an inspiring photography tour, take in the pleasant sights at Diamond Head State Monument, and see the interesting displays at USS Bowfin Submarine Museum & Park.

Plan trip to Honolulu with our itinerary maker to find out where to go and what to do.

Traveling by flight from Kihei to Honolulu takes 3 hours. Expect a daytime high around 32°C in December, and nighttime lows around 24°C. Cap off your sightseeing on the 4th (Sat) early enough to travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Pu’u O Mahuka Heiau State Monument, Kailua Beach Park
Find places to stay Dec 29 — Jan 4:
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

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