18 days in Hawaii Itinerary

18 days in Hawaii Itinerary

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Route & dates

18 days in Hawaii Itinerary

Start: Toronto
Fly:  15​h 45​min
1
Hanalei, Kauai
— 3 nights
taxi + Fly:  3​h 15​min
2
Kailua-Kona, Island of Hawaii
— 3 nights
Fly:  3​h 45​min
3
Lahaina, Maui
— 5 nights
+2
Fly + foot + bus:  4​h 30​min
4
Haleiwa, Oahu
— 4 nights
+2
bus + foot + Fly:  15​h
End: Toronto

3
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Step out of the city life by going to Anini Beach and Tunnels Beach. You'll explore the less-touristy side of things at Hanalei Beach and Queen's Bath. Take a break from Hanalei with a short trip to Waimea Canyon State Park in Waimea, about 44 minutes away. The adventure continues: tour the pleasant surroundings at Kalalau Trail, look for all kinds of wild species at Hanalei National Wildlife Refuge, discover the deep blue sea with a scuba or snorkeling tour, and take in the architecture and atmosphere at Wai`oli Hui`ia Church.

To see ratings, traveler tips, maps, and other tourist information, refer to the Hanalei online trip itinerary builder .

Toronto, Canada to Hanalei is an approximately 16-hour flight. You can also do a combination of train, car, and flight. Due to the time zone difference, you'll gain 5 hours traveling from Toronto to Hanalei. Plan for much warmer temperatures traveling from Toronto in December, with highs in Hanalei at 30°C and lows at 22°C. Finish up your sightseeing early on the 11th (Wed) so you can travel to Kailua-Kona.

Things to do in Hanalei

Parks Outdoors Wildlife

Side Trips

Kauai, Queen's Bath, Na Pali Coast State Park, Kilauea Point National Wildlife Refuge, Waimea Canyon State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Hanalei Beach ©
Hanalei Beach
Kilauea Point National Wildlife Refuge ©

3
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 Manini'owali Beach (Kua Bay) and Pu'uhonua O Honaunau National Historical Park. Your itinerary includes some good beach time at Honaunau Bay and Hapuna Beach State Recreation Area. And it doesn't end there: fulfill a lifelong dream with a swim-with-the-dolphins experience, see what you can catch with a fishing tour, contemplate the waterfront views at Kealakekua Bay, and look for gifts at The Cindy Coats Gallery.

To see other places to visit, reviews, and other tourist information, read Kailua-Kona sightseeing planner.

Traveling by combination of taxi and flight from Hanalei to Kailua-Kona takes 3.5 hours. Alternatively, you can do a combination of flight and bus. Expect a daytime high around 32°C in December, and nighttime lows around 24°C. Wrap up your sightseeing on the 14th (Sat) to allow time to travel to Lahaina.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Honaunau, Hapuna Beach State Recreation Area, Kealakekua Bay
Highlights from your plan
Honaunau Bay ©
Honaunau Bay
Hapuna Beach State Recreation Area ©
Fishing Charters & Tours

5
nights
Lahaina, Maui

Lahaina ©
Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Discover out-of-the-way places like Kahekili Beach Park and Kapalua Beach. Relax by the water at Wailea Beach Path and Kamaole Beach Park II. Venture out of the city with trips to Wailea (Pa'ako Beach (Secret Cove) & Wailea Beach), Kihei (Kalepolepo Beach Park, Stand-Up Paddleboarding, & more) and Maui Specialty Chocolate (in Kahului). Next up on the itinerary: let the river carry you with a rafting and tubing tour, discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Napili Beach, and tour the pleasant surroundings at Ho'okipa Beach Park.

To see traveler tips, other places to visit, and other tourist information, refer to the Lahaina online holiday planner .

Traveling by flight from Kailua-Kona to Lahaina takes 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and flight. In December in Lahaina, expect temperatures between 30°C during the day and 23°C at night. Wrap up your sightseeing on the 19th (Thu) early enough to travel to Haleiwa.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailea, Kihei, Ho'okipa Beach Park, Kapalua Beach, Maui Specialty Chocolate
Highlights from your plan
Napili Beach ©
Napili Beach
Wailea Beach Path ©
Wailea Beach Path
Wailea Beach ©
Wailea Beach

4
nights
Haleiwa, Oahu

Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. Discover out-of-the-way places like Banzai Pipeline and Sunset Beach Park. Visiting Turtle Bay Beach and Sharks Cove will get you outdoors. Explore Haleiwa's surroundings by going to Ka'ena Point State Park (in Waianae) and Kapolei (Ko Olina Lagoons & Dolphin & Whale Watching). And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, stop by Pakaloha Bikinis - Oahu, kick back and relax at Laniakea Beach, and take in nature's colorful creations at Waimea Valley.

For traveler tips, ratings, reviews, and tourist information, you can read our Haleiwa driving holiday site .

Traveling by combination of flight and bus from Lahaina to Haleiwa takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of ferry, flight, and bus. Expect a daytime high around 28°C in December, and nighttime lows around 20°C. Cap off your sightseeing on the 23rd (Mon) early enough to travel back home.

Things to do in Haleiwa

Outdoors Parks Beaches

Side Trips

Pupukea, Ko Olina Lagoons, Ka'ena Point State Park, Turtle Bay Beach
Highlights from your plan
Skydiving
Scuba & Snorkeling
Ko Olina Lagoons ©
Ko Olina Lagoons

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