16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii planner

Make it your trip
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Kapaa, Kauai
— 1 night
Drive
2
Princeville, Kauai
— 6 nights
Unknown
3
Lahaina, Maui
— 5 nights
Drive
4
Wailea, Maui
— 2 nights
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Kapaa, Kauai

— 1 night
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Lydgate State Park has been added to your itinerary.

To see ratings, where to stay, photos, and other tourist information, refer to the Kapaa trip site.

Boston to Kapaa is an approximately 15-hour flight. The time zone difference when traveling from Boston to Kapaa is minus 5 hours. Traveling from Boston in May, expect nights in Kapaa to be warmer, around 71°F, while days are a bit warmer, around 82°F. 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

Find places to stay May 10 — 11:
Highlights from your trip

Princeville, Kauai

— 6 nights
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. Get in touch with nature at Pali Ke Kua Beach (Hideaway s Beach) and Hanalei Valley Lookout. Step off the beaten path and head to Koke`e State Park and Hāʻena State Park. You'll find plenty of places to visit near Princeville: Pihea Trail (in Kekaha) and Waimea Canyon State Park (in Waimea). The adventure continues: look for all kinds of wild species at Hanalei National Wildlife Refuge and stop by Tahiti Nui.

To see more things to do, where to stay, photos, and tourist information, refer to the Princeville trip maker app.

Traveling by car from Kapaa to Princeville takes an hour. Alternatively, you can take a bus. 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 · Nature

Side Trips

Find places to stay May 11 — 17:

Lahaina, Maui

— 5 nights

Crown Jewel of Maui

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 day by day itinerary now includes Ho'okipa Beach Park, Lahaina Banyan Court, Napili Beach, and other attractions you added. Eschew the tourist crowds and head to Kapalua Beach and D.T. Fleming Park. And it doesn't end there: relax and rejuvenate at some of the best spas, see the interesting displays at Whale Center of the Pacific, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and stop by The Jewelry Stand Maui.

Before you visit Lahaina, use our trip planner to discover what you can do and see there.

You can fly from Princeville to Lahaina in 2.5 hours. 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 · Nature

Side Trips

Find places to stay May 17 — 22:

Wailea, Maui

— 2 nights
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): stroll through Ho'okipa Beach Park and then admire the majestic nature at Iao Valley. Keep things going the next day: enjoy the sand and surf at Wailea Beach, then relax and rejuvenate at some of the best spas, then stroll through Polo Beach, and finally kick back and relax at Wailea Beach Path.

To see more things to do, maps, and more tourist information, go to the Wailea trip planner.

Drive from Lahaina to Wailea in an hour. Alternatively, you can drive; or take a bus. Expect a daytime high around 86°F in May, and nighttime lows around 68°F. You will have some time to spend on the 24th (Sun) before leaving for home.

Things to do in Wailea

Parks · Beaches · Outdoors · Nature

Side Trips

Find places to stay May 22 — 24:

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.