14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

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Route & dates

14 days in Hawaii Itinerary

Start: Boston
Fly:  13​h
1
Honolulu, Oahu
— 4 nights
Fly:  2​h 45​min
2
Poipu, Kauai
— 3 nights
Fly:  1​h 45​min
3
Kihei, Maui
— 2 nights
Bus + Fly:  2​h 15​min
4
Kailua-Kona, Island of Hawaii
— 3 nights
Fly:  15​h 30​min
End: Boston

4
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.
Explore hidden gems such as Dolphin & Whale Watching and Zipline. Explore Honolulu's surroundings by going to Ko Olina Lagoons (in Kapolei) and Waimea Bay (in Haleiwa). There's lots more to do: trek along Koko Crater Trail, explore and take pictures at Makapuu Lighthouse Trail, examine the collection at Bishop Museum, and take an unforgettable tour with a helicopter tour.

For traveler tips, photos, other places to visit, and more tourist information, read our Honolulu trip builder.

Boston to Honolulu is an approximately 13-hour flight. The time zone difference when traveling from Boston to Honolulu is minus 5 hours. Prepare for warmer weather when traveling from Boston in October: high temperatures in Honolulu hover around 86°F and lows are around 74°F. Wrap up your sightseeing on the 25th (Wed) early enough to travel to Poipu.

Things to do in Honolulu

Parks Outdoors Trails

Side Trips

Waimea Bay, North Shore, Ko Olina Lagoons
Highlights from your plan
Koko Crater Railway Trail ©
Koko Crater Railway Trail
Helicopter Tours
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail

3
nights
Poipu, Kauai

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Discover out-of-the-way places like Na Pali Coast State Park and Scuba & Snorkeling. There's still lots to do: whizz through the canopy at some of the top local zipline courses and adventure parks, experience rural life at Kauai Coffee Company, admire the natural beauty at Allerton Garden, and stop by The Wine Shop.

For other places to visit, traveler tips, reviews, and tourist information, refer to the Poipu travel itinerary planner.

Traveling by combination of flight and taxi from Honolulu to Poipu takes 3 hours. In October, daytime highs in Poipu are 83°F, while nighttime lows are 73°F. Cap off your sightseeing on the 28th (Sat) early enough to travel to Kihei.

Things to do in Poipu

Wildlife Parks Outdoors

Side Trips

Koloa, Menehune Fishpond, Na Pali Coast State Park, Kauai Coffee Company
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Kauai Coffee Company ©
Kauai Coffee Company
Scuba & Snorkeling

2
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.
On the 28th (Sat), brush up on your knowledge of spirits at Ocean Vodka Organic Farm and Distillery, experience rural life at Surfing Goat Dairy, and then kick your exploration up a notch at some of the top local zipline courses and adventure parks. On your second day here, tour the pleasant surroundings at Napili Beach and then enjoy the sand and surf at Wailea Beach.

For traveler tips, other places to visit, where to stay, and tourist information, read our Kihei itinerary builder.

You can do a combination of taxi and flight from Poipu to Kihei in 2 hours. Expect a daytime high around 87°F in October, and nighttime lows around 69°F. Finish up your sightseeing early on the 30th (Mon) so you can travel to Kailua-Kona.

Things to do in Kihei

Outdoors Beaches Parks

Side Trips

Kula, Wailea Beach, Napili Beach
Highlights from your plan
Napili Beach ©
Napili Beach
Wailea Beach ©
Wailea Beach
Ocean Vodka Organic Farm and Distillery ©

3
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.
Explore hidden gems such as Swim with Dolphins and Manini'owali Beach (Kua Bay). Venture out of the city with trips to Jagger Museum (in Volcano), Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Kilauea Iki Trail (in Hawaii Volcanoes National Park). There's much more to do: kick back and relax at Hapuna Beach State Recreation Area, experience rural life at Mountain Thunder, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and stop by Keauhou Store.

For more things to do, reviews, other places to visit, and other tourist information, use the Kailua-Kona trip itinerary maker.

Getting from Kihei to Kailua-Kona by flight takes about 2.5 hours. In October in Kailua-Kona, expect temperatures between 85°F during the day and 74°F at night. Wrap up your sightseeing on the 2nd (Thu) early enough to travel back home.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Holualoa, Hapuna Beach State Recreation Area, Pu'uhonua O Honaunau National Historical Park, Kilauea Iki Trailhead, Greenwell Farms
Highlights from your plan
Swim with Dolphins
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead

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