15 days in Hawaii Itinerary

15 days in Hawaii Itinerary

Created using Inspirock United States travel route planner

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Route & dates

15 days in Hawaii Itinerary

Start: Saint John
Fly:  17​h
1
Kailua, Oahu
— 5 nights
Fly:  3​h 45​min
2
Hanalei
— 3 nights
Fly:  3​h 45​min
3
Kihei
— 5 nights
Drive + Fly:  18​h 45​min
End: Saint John


Learn more about your trip

5
nights
Kailua, Oahu

Kailua ©
Kailua is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Your day-by-day itinerary now includes North Shore as well as Pearl Harbor Tours. You'll get in some beach time at Lanikai Beach and Kalama Beach Park. Discover out-of-the-way places like Lanikai Pillboxes and Maunawili Falls. You'll find plenty of places to visit near Kailua: Opana Radar Site (in Kawela Bay), Ehukai Beach Park (in Pupukea) and Haleiwa (Scuba & Snorkeling & Ehukai Pillbox Hike). And it doesn't end there: enjoy the sand and surf at Bellows Field Beach Park, indulge your thirst for a good beer at Lanikai Brewing Company, tour the pleasant surroundings at Kailua Beach Park, and hike along Olomana Three Peaks Trail.

For where to stay, other places to visit, ratings, and tourist information, use the Kailua day trip planning tool .

Saint John, Canada to Kailua is an approximately 17-hour combination of flight and car. The time zone changes from Atlantic Standard Time to Hawaii Standard Time, which is usually a -6 hour difference. In May, Kailua is warmer than Saint John - with highs of 32°C and lows of 26°C. On the 21st (Thu), you'll have the morning to explore before heading off to Hanalei.

Things to do in Kailua

Outdoors Parks Beaches

Side Trips

Oahu, Haleiwa, Waimanalo, Pearl Harbor Tours, Green World Coffee Farms
Highlights from your plan
Lanikai Beach ©
Lanikai Beach
Kailua Beach Park ©
Kailua Beach Park
Makapu'u Point ©
Makapu'u Point

3
nights
Hanalei

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Explore hidden gems such as Hanalei Beach and Spas. Get outdoors at Dolphin & Whale Watching and Hanalei National Wildlife Refuge. There's lots more to do: see what you can catch with a fishing tour, trek along Nu'alolo Trail, kick back and relax at Secret Beach, and look for all kinds of wild species at Na Pali Coast State Park.

To see ratings, maps, other places to visit, and tourist information, refer to the Hanalei visit planner.

Traveling by flight from Kailua to Hanalei takes 4 hours. In May, plan for daily highs up to 32°C, and evening lows to 25°C. Finish up your sightseeing early on the 24th (Sun) so you can travel to Kihei.

Things to do in Hanalei

Outdoors Parks Wildlife

Side Trips

Kauai, Na Pali Coast State Park
Highlights from your plan
Dolphin & Whale Watching
Hanalei Beach ©
Hanalei Beach
Secret Beach ©
Secret Beach

5
nights
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.
Shop till you drop at Lahaina Cannery Mall and Pakaloha Bikinis. Get some historical perspective at Maria Lanakila Catholic Church and McGregor Point Light. Venture out of the city with trips to Pipiwai Trail (in Haleakala National Park), Baby Beach (in Lahaina) and Kapalua Beach (in Kapalua). There's lots more to do: relax and rejuvenate at some of the best spas, indulge your thirst for a good beer at Maui Brewing Company, see majestic marine mammals with a dolphin and whale watching tour, and enjoy the sand and surf at Maluaka Beach.

To find photos, ratings, reviews, and tourist information, read Kihei day trip site .

Getting from Hanalei to Kihei by flight takes about 4 hours. In May in Kihei, expect temperatures between 35°C during the day and 23°C at night. On the 29th (Fri), you'll travel back home.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Maui, Lahaina, Paia, Wailea, Red Sand Beach (Kaihalulu Beach)
Highlights from your plan
Spas
Stand-Up Paddleboarding
Ho'okipa Beach Park ©
Ho'okipa Beach Park

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