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
— 3 nights
Fly + Bus:  3 h 30 min
2
Kailua-Kona, Island of Hawaii
— 4 nights
Fly + Bus:  2 h 15 min
3
Kihei, Maui
— 4 nights
Fly + Taxi:  2 h
4
Princeville, Kauai
— 3 nights
Fly:  18 h 30 min
End: Toronto

3
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.
Step off the beaten path and head to Sunset Beach Park and Kapiolani Regional Park. Get in touch with nature at Waimea Bay and Manoa Falls. The adventure continues: tour the pleasant surroundings at Waikiki Beach, make a trip to North Shore, explore the striking landscape at Halona Blowhole, and kick back and relax at Hanauma Bay Nature Preserve.

For other places to visit, photos, and more tourist information, read Honolulu itinerary 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. Traveling from Toronto in February, things will get much hotter in Honolulu: highs are around 31°C and lows about 23°C. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Kailua-Kona.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Oahu, Haleiwa
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Sunset Beach Park ©
Sunset Beach Park

4
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.
Explore hidden gems such as Honaunau Bay and Manini'owali Beach (Kua Bay). Get in touch with nature at Greenwell Farms and Kealakekua Bay. Explore Kailua-Kona's surroundings by going to Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Big Island Bees (in Captain Cook). Next up on the itinerary: discover the deep blue sea with a scuba or snorkeling tour and relax in the rural setting at Hula Daddy Kona Coffee.

To see reviews, other places to visit, more things to do, and tourist information, you can read our Kailua-Kona custom trip planner.

Do a combination of flight and bus from Honolulu to Kailua-Kona in 3.5 hours. In February in Kailua-Kona, expect temperatures between 32°C during the day and 24°C at night. Finish your sightseeing early on the 10th (Fri) so you can travel to Kihei.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Captain Cook, Honaunau, Greenwell Farms, Hula Daddy Kona Coffee
Highlights from your plan
Honaunau Bay ©
Honaunau Bay
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)

4
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.
Discover out-of-the-way places like Stand-Up Paddleboarding and Makena Beach. Relax by the water at Ho'okipa Beach Park and Maluaka Beach. Take a break from Kihei with a short trip to Lahaina Harbor in Lahaina, about 34 minutes away. And it doesn't end there: fulfill a lifelong dream with a swim-with-the-dolphins experience, sample the fine beverages at Ocean Vodka Organic Farm and Distillery, enjoy the sand and surf at Wailea Beach Path, and take an unforgettable tour with a helicopter tour.

To see more things to do, reviews, maps, and more tourist information, refer to the Kihei trip planner.

Getting from Kailua-Kona to Kihei by flight takes about 2.5 hours. Traveling from Kailua-Kona in February, Kihei is a bit cooler at night with lows of 20°C. Finish your sightseeing early on the 14th (Tue) so you can travel to Princeville.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Kula, Lahaina, Helicopter Tours, Ho'okipa Beach Park
Highlights from your plan
Wailea Beach Path ©
Wailea Beach Path
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Makena Beach ©
Makena Beach

3
nights
Princeville, Kauai

Princeville ©
Princeville is a 9,000acre, upscale, unincorporated, master-planned community of vacation homes and condos on the north shore of the island of Kauai in Kauai County, Hawaii. Step out of the city life by going to Shipwreck Beach and Anini Beach. Discover out-of-the-way places like Hanalei Beach and Kauai Coffee Company. Explore the numerous day-trip ideas around Princeville: Lihue (Kalapaki Beach & Kōloa Rum™ Company Store). There's more to do: take in the dramatic natural features at Queen's Bath and visit a coastal fixture at Kilauea Point National Wildlife Refuge.

To see other places to visit, traveler tips, maps, and other tourist information, refer to the Princeville itinerary builder.

Traveling by combination of flight and taxi from Kihei to Princeville takes 2 hours. February in Princeville sees daily highs of 30°C and lows of 22°C at night. Finish up your sightseeing early on the 17th (Fri) so you can travel back home.

Things to do in Princeville

Parks Beaches Outdoors

Side Trips

Lihue, Kauai Coffee Company, Shipwreck Beach, Anini Beach, Hanalei Beach
Highlights from your plan
Hanalei Beach ©
Hanalei Beach
Shipwreck Beach ©
Shipwreck Beach
Anini Beach ©
Anini Beach

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