16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii attractions planner
Make it your trip
Bus to Boston, Fly to Honolulu
1
Honolulu
— 2 nights
Drive
2
Kailua
— 2 nights
Fly
3
Hilo
— 3 nights
Fly
4
Hanalei
— 6 nights
Fly

S M T W T F S
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Honolulu — 2 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Visiting Hanauma Bay Nature Preserve and Lanikai Beach will get you outdoors. Next up on the itinerary: see the vivid underwater world at Pele's Chair, take some stellar pictures from Lanikai Pillboxes, and celebrate the Hawaiian way at Hale Koa Luau.

To see maps, ratings, where to stay, and more tourist information, use the Honolulu trip planner.

Boston to Honolulu is an approximately 12.5-hour combination of bus and flight. You can also fly. The time zone difference moving from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST) is minus 5 hours. Traveling from Boston in April, expect Honolulu to be much hotter, temps between 83°F and 71°F. Wrap up your sightseeing on the 1st (Mon) early enough to drive to Kailua.
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Nightlife · Parks · Wildlife · Nature
Side Trips

Kailua — 2 nights

Kailua is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Start off your visit on the 2nd (Tue): explore the striking landscape at Halona Blowhole. Here are some ideas for day two: don't miss a visit to Makapu'u Point, find something for the whole family at Sea Life Park Hawaii, then explore the gorgeous colors at Pele's Chair, and finally stroll through Lanikai Beach.

To see ratings, maps, where to stay, and other tourist information, you can read our Kailua holiday maker site.

You can drive from Honolulu to Kailua in an hour. Alternatively, you can take a bus. In May in Kailua, expect temperatures between 82°F during the day and 72°F at night. Wrap up your sightseeing on the 3rd (Wed) to allow time to fly to Hilo.
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Parks · Wildlife · Outdoors · Theme Parks
Side Trips

Hilo — 3 nights

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.
Step out of the city life by going to Volcano Art Center Gallery and Akaka Falls State Park. Give yourself a bit of retail therapy at Big Island Candies and Banyan Gallery. Explore the numerous day-trip ideas around Hilo: Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Devastation Trail, &more) and Jagger Museum (in Volcano). There's lots more to do: take in nature's colorful creations at Liliuokalani Gardens, examine the collection at Lyman Museum, pick up some local products at Hilo Farmers Market, and take an unforgettable tour with a helicopter tour.

To find where to stay, traveler tips, reviews, and more tourist information, go to the Hilo online trip maker.

You can fly from Kailua to Hilo in 2.5 hours. Traveling from Kailua in May, plan for slightly colder nights in Hilo, with lows around 67°F. Finish up your sightseeing early on the 6th (Sat) so you can catch the flight to Hanalei.
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Parks · Shopping · Museums · Nature
Side Trips

Hanalei — 6 nights

Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. You'll get in some beach time at Hanalei Beach and Anini Beach. Step out of the city life by going to Waimea Canyon State Park and Na Pali Coast State Park. You'll find plenty of places to visit near Hanalei: Salt Pond Beach Park (in Hanapepe), Koloa Monday Farmers Market (in Koloa) and Queen's Bath (in Princeville). There's still lots to do: browse the different shops at Princeville Center, tour the pleasant surroundings at Tunnels Beach, hike along Kalalau Trail, and admire the sheer force of Hanakapiai Falls.

For ratings, where to stay, traveler tips, and other tourist information, you can read our Hanalei trip planner.

Traveling by flight from Hilo to Hanalei takes 4.5 hours. In May, daily temperatures in Hanalei can reach 82°F, while at night they dip to 71°F. Wrap up your sightseeing on the 12th (Fri) early enough to fly back home.
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Parks · Outdoors · Wildlife · Beaches
Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.
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