16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

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Route & dates

16 days in Hawaii Itinerary

Start: Boston
Fly:  15​h 15​min
1
Poipu, Kauai
— 2 nights
Drive:  1​h 15​min
2
Princeville, Kauai
— 6 nights
Taxi + Fly:  2​h
3
Wailea, Maui
— 4 nights
Bus + Fly:  2​h 30​min
4
Kailua-Kona, Island of Hawaii
— 2 nights
Fly:  15​h 30​min
End: Boston

2
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. Escape the urban bustle at Kalapaki Beach and Shipwreck Beach. Eschew the tourist crowds and head to Maha'ulepu Heritage Trail and Kauai Coffee Company. Next up on the itinerary: kick back and relax at Poipu Beach Park, discover the deep blue sea with a scuba or snorkeling tour, whizz through the canopy at some of the top local zipline courses and adventure parks, and take in the dramatic natural features at Spouting Horn.

For maps, ratings, more things to do, and other tourist information, go to the Poipu itinerary maker.

Boston to Poipu is an approximately 15.5-hour combination of flight and taxi. The time zone difference when traveling from Boston to Poipu is minus 5 hours. Traveling from Boston in May, things will get a bit warmer in Poipu: highs are around 81°F and lows about 71°F. Finish your sightseeing early on the 25th (Thu) so you can drive to Princeville.

Things to do in Poipu

Outdoors Parks Beaches

Side Trips

Kauai Coffee Company, Kalapaki Beach, Scuba & Snorkeling
Highlights from your plan
Shipwreck Beach ©
Shipwreck Beach
Kalapaki Beach ©
Kalapaki Beach
Kauai Coffee Company ©
Kauai Coffee Company

6
nights
Princeville, Kauai

Princeville ©
Princeville is a 9,000acre, upscale, unincorporated, master-planned community of vacation homes and condos on the north shore of the island of Kauai in Kauai County, Hawaii. We've included these beaches for you: Pali Ke Kua Beach (Hideaway s Beach) and Hanalei Beach. Your inner history buff will appreciate Kilauea Point National Wildlife Refuge and Waioli Huiia Church. When in Princeville, make a side trip to see Photography Tours in Kapaa, approximately 36 minutes away. Spend the 29th (Mon) observing fascinating marine mammals with a dolphin and whale watching tour. And it doesn't end there: kick back and relax at Tunnels Beach, look for gifts at Ching Young Village Shopping Center, tour the pleasant surroundings at Anini Beach, and take some stellar pictures from Hanalei Valley Lookout.

To find other places to visit, photos, and other tourist information, refer to the Princeville travel planner.

Traveling by car from Poipu to Princeville takes 1.5 hours. May in Princeville sees daily highs of 81°F and lows of 71°F at night. Finish up your sightseeing early on the 31st (Wed) so you can travel to Wailea.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Hanalei, Kauai, Photography Tours, Kilauea Point National Wildlife Refuge, Ke'e Beach
Highlights from your plan
Tunnels Beach ©
Tunnels Beach
Ke'e Beach ©
Ke'e Beach
Pali Ke Kua Beach (Hideaway s Beach) ©
Pali Ke Kua Beach (Hideaway s Beach)

4
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Step out of the city life by going to Maluaka Beach and Kamaole Beach Park II. Explore hidden gems such as Keawakapu Beach and Kamaole Beach Park III. Explore the numerous day-trip ideas around Wailea: Kapalua Beach (in Kapalua), Maui Tropical Plantation (in Wailuku) and Napili Beach (in Lahaina). There's still lots to do: enjoy the sand and surf at Makena Beach, whizz through the canopy at some of the top local zipline courses and adventure parks, and work some fitness into your day at Wailea Beach Path.

To find more things to do, reviews, and more tourist information, use the Wailea trip itinerary maker.

Getting from Princeville to Wailea by combination of taxi and flight takes about 2 hours. Expect a daytime high around 85°F in May, and nighttime lows around 68°F. Finish up your sightseeing early on the 4th (Sun) so you can travel to Kailua-Kona.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Kihei, Wailuku, Napili Beach, Kapalua Beach
Highlights from your plan
Kamaole Beach Park III ©
Kamaole Beach Park III
Keawakapu Beach ©
Keawakapu Beach
Wailea Beach Path ©
Wailea Beach Path

2
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.
Discover out-of-the-way places like Kealakekua Bay and Swim with Dolphins. Your inner history buff will appreciate Pu'uhonua O Honaunau National Historical Park and The Painted Church. There's still lots to do: experience rural life at Hula Daddy Kona Coffee, kick your exploration up a notch at some of the top local zipline courses and adventure parks, take an in-depth tour of Kona Coffee Living History Farm, and tour the pleasant surroundings at Manini'owali Beach (Kua Bay).

To find reviews, ratings, and more tourist information, go to the Kailua-Kona custom trip planner.

You can do a combination of taxi and flight from Wailea to Kailua-Kona in 2.5 hours. In June, daily temperatures in Kailua-Kona can reach 84°F, while at night they dip to 74°F. Wrap up your sightseeing on the 6th (Tue) early enough to travel back home.

Things to do in Kailua-Kona

Outdoors Parks Wildlife

Side Trips

Captain Cook, Hula Daddy Kona Coffee, Greenwell Farms, Pu'uhonua O Honaunau National Historical Park
Highlights from your plan
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Kona Coffee Living History Farm ©
Kona Coffee Living History Farm
Kealakekua Bay ©
Kealakekua Bay

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