16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Fly
1
Honolulu, Oahu
— 6 nights
Fly
2
Kihei, Maui
— 4 nights
Fly
3
Hilo, Island of Hawaii
— 2 nights
Drive
4
Kailua-Kona, Island of Hawaii
— 3 nights
Fly

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Honolulu, Oahu

— 6 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: Kailua Beach Park (in Kailua), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Haleiwa (Sunset Beach Park & Waimea Bay). There's much more to do: stroll the grounds of USS Arizona Memorial, admire the sheer force of Manoa Falls, tour the pleasant surroundings at Waikiki Beach, and make a trip to Battleship Missouri Memorial.

For reviews, other places to visit, where to stay, and other tourist information, read our Honolulu trip planner.

Toronto, Canada to Honolulu is an approximately 13.5-hour flight. You'll gain 5 hours traveling from Toronto to Honolulu due to the time zone difference. Prepare for much hotter weather when traveling from Toronto in March: high temperatures in Honolulu hover around 32°C and lows are around 23°C. Finish up your sightseeing early on the 27th (Fri) so you can travel to Kihei.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Kihei, Maui

— 4 nights
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 & Ka'anapali Beach), Ho'okipa Beach Park (in Paia) and Haleakala Crater (in Haleakala National Park). The adventure continues: cruise along Hana Highway - Road to Hana, enjoy the sand and surf at Wailea Beach, meet the residents at Maui Ocean Center, and tour the pleasant surroundings at Kalepolepo Beach Park.

To see photos, where to stay, maps, and other tourist information, you can read our Kihei trip maker tool.

Traveling by flight from Honolulu to Kihei takes 4.5 hours. In March, plan for daily highs up to 32°C, and evening lows to 21°C. Finish up your sightseeing early on the 31st (Tue) so you can travel to Hilo.

Things to do in Kihei

Parks · Outdoors · Beaches · Nature

Side Trips

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 1st (Wed): take in the dramatic scenery at Akaka Falls State Park, then take in the dramatic scenery at Rainbow Falls, then tour the pleasant surroundings at Kilauea Iki Trailhead, and finally hike along Kipuka Puaulu (Bird Park) Trail. On the 2nd (Thu), you'll have a packed day of sightseeing: admire the natural beauty at Liliuokalani Gardens, then view the masterpieces at Volcano Art Center Gallery, then cruise along Devastation Trail, and finally head outdoors with Keanakakoi Crater Overlook.

To find more things to do, ratings, where to stay, and tourist information, read Hilo trip itinerary planner.

Traveling by flight from Kihei to Hilo takes 3 hours. In March, daily temperatures in Hilo can reach 31°C, while at night they dip to 22°C. Finish your sightseeing early on the 2nd (Thu) so you can drive to Kailua-Kona.

Things to do in Hilo

Outdoors · Parks · Trails · Nature

Side Trip

Kailua-Kona, Island of Hawaii

— 3 nights

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.
Start off your visit on the 3rd (Fri): get engrossed in the history at H.N. Greenwell Store Museum, then explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, then get engrossed in the history at Kona Coffee Living History Farm, and finally get a new perspective on things with Boat Tours & Water Sports. Keep things going the next day: stroll through Mauna Kea Beach and then enjoy the sand and surf at Hapuna Beach State Recreation Area.

To find other places to visit, maps, reviews, and more tourist information, you can read our Kailua-Kona trip builder site.

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In April, daily temperatures in Kailua-Kona can reach 33°C, while at night they dip to 26°C. Wrap up your sightseeing on the 5th (Sun) to allow time to travel back home.

Things to do in Kailua-Kona

Outdoors · Parks · Beaches · Nature

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
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.