17 days in Hawaii Itinerary

17 days in Hawaii Itinerary

Created using Inspirock Hawaii Trip Planner

This plan was created by another user. Make it your plan

Route & dates

17 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
— 5 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 Scuba & Snorkeling. And it doesn't end there: experience rural life at Kauai Coffee Company, kick your exploration up a notch at some of the top local zipline courses and adventure parks, enjoy the sand and surf at Poipu Beach Park, and explore the striking landscape at Spouting Horn.

To find traveler tips, ratings, other places to visit, and more tourist information, you can read our Poipu trip generator.

Boston to Poipu is an approximately 15.5-hour combination of flight and taxi. The time zone difference moving from Eastern Standard Time to Hawaii Standard Time is minus 5 hours. Plan for a bit warmer temperatures traveling from Boston in May, with highs in Poipu at 81°F and lows at 71°F. Finish your sightseeing early on the 24th (Wed) so you can drive to Princeville.

Things to do in Poipu

Outdoors Parks Beaches

Side Trips

Kauai Coffee Company, Scuba & Snorkeling, Kalapaki Beach
Highlights from your plan
Shipwreck Beach ©
Shipwreck Beach
Kalapaki Beach ©
Kalapaki Beach
Poipu Beach Park ©
Poipu Beach 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. Relax by the water at Pali Ke Kua Beach (Hideaway s Beach) and Anini Beach. Take a break from the city and head to Ke'e Beach and Kalalau Trail. When in Princeville, make a side trip to see Kauai Path in Kapaa, approximately 36 minutes away. Spend the 28th (Sun) observing fascinating marine mammals with a dolphin and whale watching tour. The adventure continues: kick back and relax at Tunnels Beach, examine the collection at Waioli Mission House, take in the architecture and atmosphere at Waioli Huiia Church, and stroll through Hanalei Beach.

To see other places to visit, more things to do, and tourist information, read Princeville holiday 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 30th (Tue) so you can travel to Wailea.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Hanalei, Kauai, Kauai Path, Ke'e Beach
Highlights from your plan
Ke'e Beach ©
Ke'e Beach
Pali Ke Kua Beach (Hideaway s Beach) ©
Tunnels Beach ©
Tunnels Beach

5
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Discover out-of-the-way places like Maluaka Beach and Kamaole Beach Park III. Visit Ulua Beach and Kapalua Beach for some beach relaxation. Get out of town with these interesting Wailea side-trips: Ho'okipa Beach Park (in Paia), Haliimaile Distilling Company (in Makawao) and Zipline (in Haleakala National Park). There's much more to do: kick back and relax at Kamaole Beach Park II, stroll through Wailea Beach, get some jogging in at Wailea Beach Path, and look for gifts at Sweet Paradise Chocolatier.

To see more things to do, photos, ratings, and other tourist information, read Wailea trip itinerary builder.

You can do a combination of taxi and flight from Princeville to Wailea in 2 hours. In May, daytime highs in Wailea are 85°F, while nighttime lows are 68°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel to Kailua-Kona.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Kihei, Kapalua Beach, Haliimaile Distilling Company, Ho'okipa Beach Park, Napili Beach
Highlights from your plan
Ulua Beach ©
Ulua Beach
Wailea Beach Path ©
Wailea Beach Path
Ho'okipa Beach Park ©
Ho'okipa Beach Park

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.
You'll enjoy a bit of beach vacationing at Manini'owali Beach (Kua Bay) and Kahaluu Beach. Discover out-of-the-way places like Greenwell Farms and Swim with Dolphins. Get out of town with these interesting Kailua-Kona side-trips: Kealakekua Bay (in Captain Cook) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). And it doesn't end there: 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, and explore the galleries of Kona Coffee Living History Farm.

To see other places to visit, reviews, photos, and tourist information, you can read our Kailua-Kona travel itinerary creator.

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

Things to do in Kailua-Kona

Outdoors Parks Wildlife

Side Trips

Captain Cook, Kahaluu Beach, Hula Daddy Kona Coffee, Pu'uhonua O Honaunau National Historical Park, Greenwell Farms
Highlights from your plan
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Kahaluu Beach ©
Kahaluu Beach
Swim with Dolphins

Similar Plans

19 days in Hawaii BY A USER FROM UNITED STATES August, teens, kids, culture, outdoors, romantic, beaches, historic sites, hidden gems PREFERENCES: August, teens, kids, culture, outdoors, romantic, beaches, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 60 days in Hawaii BY A USER FROM NEW ZEALAND March, teens, kids, culture, relaxing, beaches, historic sites, shopping, popular sights PREFERENCES: March, teens, kids, culture, relaxing, beaches, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 19 days in Hawaii BY A USER FROM CANADA April, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: April, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 18 days in Hawaii BY A USER FROM AUSTRALIA April, teens, kids, culture, outdoors, relaxing, beaches, hidden gems PREFERENCES: April, teens, kids, culture, outdoors, relaxing, beaches ATTRACTION STYLE: Hidden gems PACE: Medium 15 days in Hawaii BY A USER FROM CANADA December, teens, kids, culture, beaches, historic sites, popular sights PREFERENCES: December, teens, kids, culture, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 29 days in Hawaii BY A USER FROM AUSTRALIA August, culture, relaxing, historic sites, museums, shopping, slow & easy, popular sights PREFERENCES: August, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 18 days in Hawaii BY A USER FROM AUSTRALIA May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 18 days in Hawaii BY A USER FROM CANADA March, popular & hidden gems PREFERENCES: March ATTRACTION STYLE: Popular & hidden gems PACE: Medium 19 days in Hawaii BY A USER FROM UNITED STATES September, popular & hidden gems PREFERENCES: September ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Hawaii BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Hawaii BY A USER FROM CANADA June, culture, outdoors, historic sites, fast-paced, popular sights PREFERENCES: June, culture, outdoors, historic sites ATTRACTION STYLE: Popular sights PACE: Fast-paced 28 days in Hawaii BY A USER FROM AUSTRALIA March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, fast-paced, popular sights PREFERENCES: March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Fast-paced
See more plans