17 days in Hawaii Itinerary

17 days in Hawaii Itinerary

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Route & dates

17 days in Hawaii Itinerary

Start: Regina
Fly:  12 h
1
Kailua-Kona, Island of Hawaii
— 2 nights
Drive:  1 h 45 min
2
Hilo, Island of Hawaii
— 2 nights
Fly:  2 h 30 min
3
Honolulu, Oahu
— 6 nights
Fly:  3 h 15 min
4
Lahaina, Maui
— 6 nights
Bus + Fly:  13 h
End: Regina

2
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.
On the 12th (Sun), you'll have a packed day of sightseeing: stop by The Original Donkey Ball Store, then stroll through Pu'uhonua O Honaunau National Historical Park, then kick back and relax at Kahaluu Beach, and finally fulfill a lifelong dream with a swim-with-the-dolphins experience.

For maps, where to stay, photos, and tourist information, use the Kailua-Kona road trip planning website.

Regina, Canada to Kailua-Kona is an approximately 12-hour flight. You'll gain 4 hours traveling from Regina to Kailua-Kona due to the time zone difference. Expect somewhat warmer weather when traveling from Regina in July: highs in Kailua-Kona hover around 35°C, while lows dip to 28°C. Finish up your sightseeing early on the 13th (Mon) so you can go by car to Hilo.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Kahaluu Beach, Puako Petroglyph Archaeological Preserve, Hapuna Beach State Recreation Area, The Original Donkey Ball Store, Puukohola National Historic Park
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

2
nights
Hilo, Island of Hawaii

Hilo ©
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.
On the 14th (Tue), take a memorable drive along Devastation Trail, then trek along Kilauea Iki Trailhead, then shop like a local with Volcano Art Center Gallery, and finally examine the collection at Jagger Museum. Keep things going the next day: pick up some local products at Hilo Farmers Market, admire the natural beauty at Liliuokalani Gardens, then stop by Big Island Candies, and finally admire the majestic nature at Akaka Falls State Park.

To find more things to do, ratings, traveler tips, and other tourist information, go to the Hilo travel itinerary planner.

Drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Expect a bit cooler evenings in Hilo when traveling from Kailua-Kona in July, with lows around 25°C. Cap off your sightseeing on the 15th (Wed) early enough to travel to Honolulu.

Things to do in Hilo

Shopping Parks Outdoors

Side Trips

Hawaii Volcanoes National Park, Big Island Candies, Jagger Museum
Highlights from your plan
Volcano Art Center Gallery ©
Volcano Art Center Gallery
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Akaka Falls State Park ©
Akaka Falls State Park

6
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.
For shopping fun, head to Ala Moana Center or Ko Hana Distillers. You'll enjoy a bit of beach vacationing at Waikiki Beach and Kapiolani Regional Park. Venture out of the city with trips to Kailua (Kailua Beach Park & Lanikai Beach), Haleiwa (Waimea Bay & Sunset Beach Park) and Swim with Dolphins (in Waianae). And it doesn't end there: take in the pleasant sights at Diamond Head State Monument, get great views at Puu Ualakaa State Park, browse the different shops at Ward Village, and examine the collection at USS Bowfin Submarine Museum & Park.

Planning Honolulu trip won't be overwheling when you use's Insprock itinerary maker.

You can fly from Hilo to Honolulu in 2.5 hours. In July, daily temperatures in Honolulu can reach 36°C, while at night they dip to 28°C. Wrap up your sightseeing on the 21st (Tue) to allow time to travel to Lahaina.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Kailua, Haleiwa, Ko Hana Distillers, Swim with Dolphins
Highlights from your plan
Ala Moana Center ©
Ala Moana Center
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

6
nights
Lahaina, Maui

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.
Visit Ka'anapali Beach and Napili Beach for some beach relaxation. Get outdoors at Scuba & Snorkeling and Iao Valley. Explore Lahaina's surroundings by going to Kalepolepo Beach Park (in Kihei), Haleakala Crater (in Haleakala National Park) and Laura Mango Art Gallery (in Hana). The adventure continues: tour the pleasant surroundings at Wailea Beach, take in the exciting artwork at Village Galleries in Lahaina, stop by Sand People, and enjoy the sand and surf at Ho'okipa Beach Park.

To see maps, reviews, where to stay, and other tourist information, go to the Lahaina road trip planning app.

Traveling by flight from Honolulu to Lahaina takes 3.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight and bus. July in Lahaina sees daily highs of 35°C and lows of 26°C at night. Wrap up your sightseeing on the 27th (Mon) to allow time to travel back home.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailuku, Kapalua, Kalepolepo Beach Park, Ho'okipa Beach Park, Haleakala Crater
Highlights from your plan
Scuba & Snorkeling
Haleakala Crater ©
Haleakala Crater
Ka'anapali Beach ©
Ka'anapali Beach

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