16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

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Route & dates

16 days in Hawaii Itinerary

Start: Boston
Fly:  14 h
1
Kapaa, Kauai
— 1 night
Drive:  1 h
2
Princeville, Kauai
— 6 nights
Fly + Bus:  1 h 30 min
3
Lahaina, Maui
— 5 nights
Drive:  1 h
4
Wailea, Maui
— 2 nights
Fly:  15 h 15 min
End: Boston

1
night
Kapaa, Kauai

Kapaa ©
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Your day-by-day itinerary now includes Lydgate State Park.

To see where to stay, more things to do, photos, and other tourist information, read our Kapaa online travel planner.

Boston to Kapaa is an approximately 15.5- hour flight. You can also do a combination of train and flight. The time zone difference when traveling from Boston to Kapaa is minus 5 hours. When traveling from Boston in May, plan for somewhat warmer days and much hotter nights in Kapaa: temperatures range from 82°F by day to 71°F at night. On the 11th (Mon), wrap the sightseeing up by early afternoon so you can drive to Princeville.

Things to do in Kapaa

Parks

Side Trip

Lydgate State Park
Highlights from your plan
Lydgate State Park ©
Lydgate State Park

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. Your day-by-day itinerary now includes Hanalei Day Spa, Hanalei Beach, Hanalei Bay, and other attractions you added. You'll explore the less-touristy side of things at Pali Ke Kua Beach (Hideaway s Beach) and Hanalei Valley Lookout. Explore Princeville's surroundings by going to Waimea Canyon State Park (in Waimea) and Kekaha (Pihea Trail & Koke`e State Park). There's lots more to do: immerse yourself in nature at Hāʻena State Park, identify plant and animal life at Hanalei National Wildlife Refuge, and look for gifts at Tahiti Nui.

To find other places to visit, where to stay, photos, and tourist information, go to the Princeville travel route planner.

Getting from Kapaa to Princeville by car takes about an hour. In May in Princeville, expect temperatures between 82°F during the day and 71°F at night. You will have some time to spend on the 17th (Sun) before leaving for Lahaina.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Kauai, Hanalei, Kekaha, Waimea Canyon State Park, Ke'e Beach
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Ke'e Beach ©
Ke'e Beach
Hanalei Beach ©
Hanalei Beach

5
nights
Lahaina, Maui

Lahaina ©
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.
Your list of things to see and do now includes Ho'okipa Beach Park, Lahaina Banyan Court, Napili Beach, and other attractions. Relax by the water at Kapalua Beach and D.T. Fleming Park. Discover out-of-the-way places like Spas and The King's Taro Patch. There's lots more to do: kick your exploration up a notch at categoryPhrases.alias.some_of_the_top_local_zipline_courses_and_adventure_parks, examine the collection at Whale Center of the Pacific, and look for gifts at The Jewelry Stand Maui.

For other places to visit, maps, where to stay, and more tourist information, go to the Lahaina trip planning site.

You can do a combination of flight and bus from Princeville to Lahaina in 4 hours. Another option is to fly. Expect a daytime high around 81°F in May, and nighttime lows around 70°F. You will have some time to spend on the 22nd (Fri) before leaving for Wailea.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Hana, Kapalua, Lanai, Nakalele Blowhole, Lanai Cat Sanctuary
Highlights from your plan
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Kapalua Beach ©
Kapalua Beach
Lanai Cat Sanctuary ©
Lanai Cat Sanctuary

2
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Your day-by-day itinerary now includes Wailea Beach Path, Iao Valley, Wailea Beach, and other attractions you added. Kick off your visit on the 22nd (Fri): tour the pleasant surroundings at Ho'okipa Beach Park and then admire the majestic nature at Iao Valley. On the 23rd (Sat), you'll have a packed day of sightseeing: kick back and relax at Wailea Beach, indulge in some personalized pampering at some of the best spas, then kick back and relax at Polo Beach, and finally kick back and relax at Wailea Beach Path.

To find more things to do, ratings, where to stay, and more tourist information, read Wailea trip builder site.

You can do a combination of bus and taxi from Lahaina to Wailea in an hour. Alternatively, you can drive. In May in Wailea, expect temperatures between 86°F during the day and 68°F at night. You'll have a few hours on the 24th (Sun) to wrap things up before traveling home.

Things to do in Wailea

Parks Outdoors Beaches

Side Trips

Iao Valley, Ho'okipa Beach Park
Highlights from your plan
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Wailea Beach ©
Wailea Beach
Wailea Beach Path ©
Wailea Beach Path

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