17 days in Hawaii Itinerary

17 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route planner

Make it your trip
Hilo, Island of Hawaii
— 2 nights
Kailua-Kona, Island of Hawaii
— 2 nights
Koloa, Kauai
— 7 nights
Honolulu, Oahu
— 4 nights


Hilo, Island of Hawaii

— 2 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Kick off your visit on the 11th (Tue): pick up some local products at Hilo Farmers Market, take in the dramatic scenery at Rainbow Falls, then admire the majestic nature at Akaka Falls State Park, and finally explore the striking landscape at Thurston Lava Tube (Nahuku). On the 12th (Wed), you'll have a packed day of sightseeing: trek along Kipuka Puaulu (Bird Park) Trail, see the interesting displays at Jagger Museum, and then contemplate the geological forces at Kīlauea.

To find reviews, photos, maps, and other tourist information, read our Hilo trip planner.

Boston to Hilo is an approximately 15-hour flight. You'll gain 5 hours traveling from Boston to Hilo due to the time zone difference. Traveling from Boston in January, expect Hilo to be much warmer, temps between 81°F and 64°F. Wrap up your sightseeing on the 12th (Wed) to allow time to drive to Kailua-Kona.

Things to do in Hilo

Parks · Nature · Trails · Outdoors

Side Trips

Kailua-Kona, Island of Hawaii

— 2 nights

Heart of the Kona Coast

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.
Keep things going the next day: take in the awesome beauty at Mauna Kea.

For ratings, maps, more things to do, and tourist information, read our Kailua-Kona day trip planning tool.

You can drive from Hilo to Kailua-Kona in 2 hours. Another option is to take a bus. January in Kailua-Kona sees daily highs of 80°F and lows of 67°F at night. Finish up your sightseeing early on the 14th (Fri) so you can catch the flight to Koloa.

Things to do in Kailua-Kona

Parks · Nature · Beaches · Outdoors

Side Trips

Koloa, Kauai

— 7 nights
Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Step out of the city life by going to Poipu Beach Park and Hanalei Beach. Your cultural itinerary includes sights like Seductions of Kauai Gallery and Lawai International Center. Get out of town with these interesting Koloa side-trips: Wailua River State Park (in Wailua), Na Pali Coast State Park (in Wainiha) and Waimea Canyon State Park (in Waimea). Next up on the itinerary: tour the pleasant surroundings at Shipwreck Beach, take in the dramatic natural features at Spouting Horn, pause for some serene contemplation at St. Raphael Church, and get engrossed in the history at Kauai Museum.

You can plan Koloa trip in no time by asking Inspirock to help create your itinerary.

You can fly from Kailua-Kona to Koloa in 2.5 hours. In January, plan for daily highs up to 79°F, and evening lows to 65°F. Finish your sightseeing early on the 21st (Fri) so you can fly to Honolulu.

Things to do in Koloa

Parks · Historic Sites · Nature · Beaches

Side Trips

Honolulu, Oahu

— 4 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.
USS Arizona Memorial and Iolani Palace will appeal to history buffs. Take a break from the city and head to Diamond Head State Monument and Hanauma Bay Nature Preserve. The adventure continues: kick back and relax at Waikiki Beach and pause for some photo ops at King Kamehameha Statue.

To find photos, more things to do, other places to visit, and other tourist information, use the Honolulu trip itinerary maker app.

Traveling by flight from Koloa to Honolulu takes 2.5 hours. In January in Honolulu, expect temperatures between 81°F during the day and 67°F at night. On the 25th (Tue), you're off to home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Hawaii travel guide

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.