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: Chicago
Fly:  13 h
1
Honolulu, Oahu
— 5 nights
Fly:  2 h
2
Kailua-Kona, Island of Hawaii
— 3 nights
Fly + Bus:  2 h
3
Kihei, Maui
— 4 nights
Taxi + Fly:  1 h 15 min
4
Lihue, Kauai
— 3 nights
Fly:  12 h 15 min
End: Chicago

5
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your list of things to see and do now includes Friday Night Fireworks at Hilton Hawaiian Village Waikiki Beach Resort, Nuuanu Pali Lookout, The Byodo-In Temple, and other attractions.

To see where to stay, traveler tips, maps, and more tourist information, read Honolulu holiday planner.

Chicago to Honolulu is an approximately 11.5-hour combination of subway and flight. The time zone difference when traveling from Chicago to Honolulu is minus 4 hours. Expect much warmer temperatures when traveling from Chicago in February; daily highs in Honolulu reach 80°F and lows reach 68°F. You will leave for Kailua-Kona on the 11th (Sun).

Things to do in Honolulu

Shopping Parks Beaches

Side Trips

Oahu, Haleiwa, Turtle Bay Beach, Dole Plantation, Banzai Pipeline
Highlights from your plan
Duke's Marketplace ©
Duke's Marketplace
Sunset Beach Park ©
Sunset Beach Park
Turtle Bay Beach ©
Turtle Bay Beach

3
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.
South Point (Ka Lae) and Green Sand Beach has been added to your itinerary. When in Kailua-Kona, make a side trip to see The Painted Church in Honaunau, approximately 38 minutes away.

To find reviews, photos, traveler tips, and tourist information, read Kailua-Kona trip generator.

Getting from Honolulu to Kailua-Kona by combination of flight and bus takes about 3.5 hours. February in Kailua-Kona sees daily highs of 81°F and lows of 69°F at night. Finish your sightseeing early on the 14th (Wed) to allow enough time to travel to Lihue.

Things to do in Kailua-Kona

Historic Sites Beaches Parks

Side Trips

The Painted Church, Papakōlea Green Sand Beach
Highlights from your plan
Papakōlea Green Sand Beach ©
Papakōlea Green Sand Beach

4
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Step off the beaten path and head to Kamaole Beach Park II and Stand-Up Paddleboarding. You'll get in some beach time at Kamaole Beach Park III and Ka'anapali Beach. Get out of town with these interesting Kihei side-trips: Lahaina (Kayaking & Canoeing, Glass Mango, & more). It doesn't end there: look for gifts at Sweet Paradise Chocolatier.

For ratings, maps, and other tourist information, refer to the Kihei custom trip planner.

Fly from Kailua-Kona to Kihei in 2.5 hours. Traveling from Kailua-Kona in February, expect little chillier with lows of 63°F in Kihei. Wrap up your sightseeing on the 18th (Sun) early enough to travel to Lihue.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Lahaina, Sweet Paradise Chocolatier
Highlights from your plan
Kamaole Beach Park II ©
Kamaole Beach Park II
Kamaole Beach Park III ©
Kamaole Beach Park III
Kayaking & Canoeing

3
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Your list of things to see and do now includes Kaakaaniu Plantation Tours, Opaekaa Falls, Fern Grotto, and other attractions. You'll discover tucked-away gems like Kilauea Point National Wildlife Refuge and Hanalei Valley Lookout. Your itinerary includes some good beach time at Pali Ke Kua Beach (Hideaway s Beach) and Makawehi Bluff. When in Lihue, make a side trip to see Scuba & Snorkeling in Poipu, approximately 40 minutes away. Next up on the itinerary: take in the dramatic natural features at Spouting Horn.

To see ratings, other places to visit, where to stay, and more tourist information, you can read our Lihue trip itinerary maker.

You can fly from Kailua-Kona to Lihue in 4 hours. In February, daytime highs in Lihue are 78°F, while nighttime lows are 66°F. You'll have a few hours on the 18th (Sun) to wrap things up before traveling to Kihei.

Things to do in Lihue

Parks Nature Outdoors

Side Trips

Kilauea, Poipu, Kauai, Hanalei, Pali Ke Kua Beach (Hideaway s Beach)
Highlights from your plan
Makawehi Bluff ©
Makawehi Bluff
Pali Ke Kua Beach (Hideaway s Beach) ©
Hanakapiai Falls ©
Hanakapiai Falls

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 21 days in Hawaii BY A USER FROM FRANCE August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 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 20 days in Hawaii BY A USER FROM GERMANY November, outdoors, relaxing, romantic, beaches, popular sights PREFERENCES: November, outdoors, relaxing, romantic, beaches 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 16 days in Hawaii BY A USER FROM CANADA August, kids, beaches, slow & easy, popular & hidden gems PREFERENCES: August, kids, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 16 days in Hawaii BY A USER FROM UNITED STATES June, teens, popular sights PREFERENCES: June, teens ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Hawaii BY A USER FROM CANADA June, romantic, beaches, hidden gems PREFERENCES: June, romantic, 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 18 days in United States BY A USER FROM IRELAND January, popular sights PREFERENCES: January ATTRACTION STYLE: Popular sights PACE: Medium
See more plans