16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

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Route & dates

16 days in Hawaii Itinerary

Start: Toronto
Fly:  13 h 15 min
1
Honolulu, Oahu
— 5 nights
+2
Fly + Taxi + Bus:  3 h 45 min
2
Volcano, Island of Hawaii
— 1 night
Drive:  1 h 45 min
3
Kailua-Kona, Island of Hawaii
— 4 nights
Fly + Bus:  2 h 15 min
4
Kihei, Maui
— 4 nights
Bus + Fly:  17 h
End: Toronto

5
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.
Discover out-of-the-way places like Dolphin & Whale Watching and Zipline. Explore Honolulu's surroundings by going to Haleiwa (Waimea Bay & Waimea Valley) and Waianae (Nature & Wildlife Tours & Ka'ena Point State Park). There's much more to do: steep yourself in history at USS Arizona Memorial, kick back and relax at Hanauma Bay Nature Preserve, stroll through Kapiolani Regional Park, and stroll the grounds of National Memorial Cemetery-Pacific.

To find reviews, ratings, photos, and more tourist information, you can read our Honolulu travel itinerary creator.

Toronto, Canada to Honolulu is an approximately 13.5-hour flight. The time zone changes from Eastern Standard Time to Hawaii Standard Time, which is usually a -5 hour difference. Prepare for a bit warmer weather when traveling from Toronto in May: high temperatures in Honolulu hover around 34°C and lows are around 26°C. Wrap up your sightseeing on the 24th (Wed) early enough to travel to Volcano.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Ka'ena Point State Park
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

1
night
Volcano, Island of Hawaii

Volcano ©
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Kick off your visit on the 24th (Wed): see the interesting displays at Jagger Museum, hike along Kilauea Iki Trail, and then explore the striking landscape at Thurston Lava Tube (Nahuku). On the 25th (Thu), you'll have a packed day of sightseeing: take in nature's colorful creations at Liliuokalani Park and Gardens, then stop by Hilo Farmers Market, and then take in nature's colorful creations at Hawaii Tropical Botanical Garden.

To see other places to visit, reviews, and more tourist information, you can read our Volcano trip itinerary builder.

Use the Route module to find suitable travel options from Honolulu to Volcano. Traveling from Honolulu in May, expect little chillier with lows of 22°C in Volcano. Cap off your sightseeing on the 25th (Thu) early enough to travel to Kailua-Kona.

Things to do in Volcano

Parks Wildlife Nature

Side Trips

Hilo, Hawaii Volcanoes National Park, Hawaii Tropical Botanical Garden
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Hawaii Tropical Botanical Garden ©
Hawaii Tropical Botanical Garden
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)

4
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.
Eschew the tourist crowds and head to Manini'owali Beach (Kua Bay) and Greenwell Farms. Take a break from Kailua-Kona with a short trip to Pu'uhonua O Honaunau National Historical Park in Honaunau, about 40 minutes away. There's lots more to do: take an unforgettable tour with a helicopter tour, glide peacefully along the water with some of the best stand-up paddleboarding in the area, take in the spiritual surroundings of Mokuaikaua Church, and get close to the beloved marine mammals with a swim-with-the-dolphins experience.

For traveler tips, maps, where to stay, and tourist information, refer to the Kailua-Kona trip itinerary planner.

The Route module can help you plan travel from Volcano to Kailua-Kona. Plan for somewhat warmer nights when traveling from Volcano in May since evenings lows in Kailua-Kona dip to 26°C. Cap off your sightseeing on the 29th (Mon) early enough to travel to Kihei.

Things to do in Kailua-Kona

Tours Outdoors Wildlife

Side Trips

Greenwell Farms, Hula Daddy Kona Coffee, Pu'uhonua O Honaunau National Historical Park
Highlights from your plan
Helicopter Tours
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Swim with Dolphins

4
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.
You'll discover tucked-away gems like Zipline and Pipiwai Trail. Explore Kihei's surroundings by going to Makawao (Food Tours, Hui Noeau Visual Arts Center, & more) and Lahaina (River Rafting & Tubing, Whalers Village Museum, & more). The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, sample the fine beverages at Ocean Vodka Organic Farm and Distillery, relax in the rural setting at Surfing Goat Dairy, and stroll through Maui Tropical Plantation.

For other places to visit, where to stay, ratings, and other tourist information, refer to the Kihei travel itinerary planner.

Traveling by flight from Kailua-Kona to Kihei takes 2.5 hours. Plan for little chillier nights when traveling from Kailua-Kona in May since evenings lows in Kihei dip to 22°C. Finish your sightseeing early on the 2nd (Fri) so you can travel back home.

Things to do in Kihei

Outdoors Tours Adventure

Side Trips

Lahaina, Kula, Maui Tropical Plantation, Pipiwai Trail, Zipline
Highlights from your plan
Zipline
Kayaking & Canoeing

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