16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock United States trip planner

Make it your trip
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Wailea, Maui
— 3 nights
Drive
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Ka'anapali, Maui
— 2 nights
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Poipu
— 4 nights
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Honolulu, Oahu
— 5 nights
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Wailea, Maui

— 3 nights
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Your day by day itinerary now includes Wailea Beach, Haleakala Crater and Hana Highway - Road to Hana. Keep things going the next day: take a memorable drive along Hana Highway - Road to Hana.

To find reviews, traveler tips, other places to visit, and more tourist information, refer to the Wailea day trip planning tool.

Boston to Wailea is an approximately 15-hour flight. The time zone difference moving from Eastern Standard Time to Hawaii-Aleutian Standard Time is minus 5 hours. In August, Wailea is a bit warmer than Boston - with highs of 90°F and lows of 73°F. On the 4th (Tue), you'll have the morning to explore before heading off to Ka'anapali.

Things to do in Wailea

Outdoors · Scenic Drive · Parks · Beaches

Side Trips

Ka'anapali, Maui

— 2 nights
Perched at the western tip of Maui, the tourist hub of Ka'anapali offers a range of resorts and activities revolving around the beach.
To find traveler tips, more things to do, and tourist information, read our Ka'anapali trip site.

Drive from Wailea to Ka'anapali in an hour. Alternatively, you can drive; or take a bus. August in Ka'anapali sees daily highs of 86°F and lows of 74°F at night. On the 6th (Thu), wrap the sightseeing up by early afternoon so you can fly to Poipu.

Things to do in Ka'anapali

Outdoors · Tours · Parks · Wildlife

Poipu

— 4 nights
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. state of Hawaii. Before you visit Poipu, use our trip planner to discover what you can do and see there.

Getting from Ka'anapali to Poipu by flight takes about 4 hours. August in Poipu sees daily highs of 86°F and lows of 76°F at night. Wrap up your sightseeing by early afternoon on the 10th (Mon) to allow enough time to fly to Honolulu.

Things to do in Poipu

Outdoors · Tours · Parks · Wildlife

Honolulu, Oahu

— 5 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day by day itinerary now includes USS Arizona Memorial, Diamond Head State Monument and Waikiki Beach.

Plan trip to Honolulu with our itinerary maker to find out where to go and what to do.

Getting from Poipu to Honolulu by flight takes about 2.5 hours. Expect a daytime high around 88°F in August, and nighttime lows around 75°F. On the 15th (Sat), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

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.

Kauai travel guide

4.5
Scuba & Snorkeling · Zipline · Beaches
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.