30 days in Hawaii Itinerary

30 days in Hawaii Itinerary

Created using Inspirock Hawaii visit planner

Make it your trip
Fly
1
Princeville, Kauai
— 7 nights
Fly
2
Honolulu, Oahu
— 5 nights
Fly to Hoolehua, Taxi to Molokai
3
Molokai
— 2 nights
Taxi to Hoolehua, Fly to Lahaina
4
Lahaina, Maui
— 2 nights
Drive
5
Kihei, Maui
— 6 nights
Fly
6
Kailua-Kona, Island of Hawaii
— 7 nights
Fly

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Princeville, Kauai

— 7 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. Eschew the tourist crowds and head to Hanalei Valley Lookout and Puu Hinahina Lookout. Venture out of the city with trips to Koke`e State Park (in Kekaha) and Puuo Kila (in Waimea). Next up on the itinerary: experience rural life at Hawaiian Organic Noni Farm, admire the majestic nature at Hāʻena State Park, stroll through Secret Beach, and discover the deep blue sea with Reef Guides Hawaii.

To see maps, other places to visit, more things to do, and more tourist information, go to the Princeville attractions planner.

Vancouver, Canada to Princeville is an approximately 9.5-hour flight. The time zone difference when traveling from Vancouver to Princeville is minus 2 hours. Prepare for warmer weather when traveling from Vancouver in January: high temperatures in Princeville hover around 79°F and lows are around 65°F. Wrap up your sightseeing on the 8th (Sat) to allow time to fly to Honolulu.

Things to do in Princeville

Outdoors · Parks · Wildlife · Nature

Side Trips

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.
You'll explore the less-touristy side of things at Waikiki Beach Walk and Pearl Harbor Aviation Museum. Get out of town with these interesting Honolulu side-trips: Kahuku Farms (in Kahuku), Banzai Pipeline (in Pupukea) and Haleiwa (Sunset Beach Park & Waimea Bay). There's lots more to do: trek along Koko Crater Railway Trail, take in the dramatic natural features at Ka'ena Point State Park, enjoy the sand and surf at Lanikai Beach, and tour the pleasant surroundings at Kailua Beach Park.

Take the guesswork out of planning a Honolulu vacation by using our trip itinerary maker.

Fly from Princeville to Honolulu in 2.5 hours. In January, plan for daily highs up to 81°F, and evening lows to 67°F. Wrap up your sightseeing on the 13th (Thu) to allow time to travel to Molokai.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Molokai

— 2 nights

The Friendly Isle

Start off your visit on the 14th (Fri): make a trip to United States Postal Service, then explore the ancient world of Ili'ili'opae Heiau, then admire the sheer force of Halawa Falls, and finally immerse yourself in nature at Palaau State Park. Keep things going the next day: stroll through Kawakiu Beach, then tour the pleasant surroundings at Waialua Beach, and then appreciate the history behind Molokai War Memorial.

To find reviews, where to stay, other places to visit, and more tourist information, use the Molokai route planning website.

Do a combination of flight and taxi from Honolulu to Molokai in 2.5 hours. January in Molokai sees daily highs of 79°F and lows of 64°F at night. Finish your sightseeing early on the 15th (Sat) to allow enough time to travel to Lahaina.

Things to do in Molokai

Parks · Outdoors · Beaches · Nature

Lahaina, Maui

— 2 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.
On the 16th (Sun), contemplate the long history of Old Lahaina Courthouse, experience rural life at Punakea Palms, and then get a new perspective on things with Boat Tours & Water Sports. On the next day, explore the activities along Lahaina Harbor, then take an in-depth tour of Baldwin Home Museum, then don't miss a visit to Dragon's Teeth, and finally enjoy the sand and surf at Kahekili Beach Park.

To find ratings, other places to visit, photos, and more tourist information, go to the Lahaina tour itinerary planner.

You can do a combination of taxi and flight from Molokai to Lahaina in 2.5 hours. January in Lahaina sees daily highs of 78°F and lows of 67°F at night. Wrap up your sightseeing on the 17th (Mon) to allow time to drive to Kihei.

Things to do in Lahaina

Parks · Outdoors · Nature · Tours

Side Trip

Kihei, Maui

— 6 nights
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.
You'll discover tucked-away gems like Wailea Beach Path and Saint Theresa Roman Catholic Church. Change things up with a short trip to Sliding Sands Trail in Haleakala National Park (about 40 minutes away). And it doesn't end there: take in the architecture and atmosphere at Keawala'i Congregational Church, make a trip to Maalaea, take in the pleasant sights at Kealia Coastal Boardwalk, and tour the pleasant surroundings at Kealia Pond National Wildlife Refuge.

For where to stay, more things to do, and other tourist information, you can read our Kihei visit planner.

You can drive from Lahaina to Kihei in an hour. Alternatively, you can take a bus. In January in Kihei, expect temperatures between 81°F during the day and 63°F at night. Cap off your sightseeing on the 23rd (Sun) early enough to catch the flight to Kailua-Kona.

Things to do in Kihei

Outdoors · Parks · Beaches · Wildlife

Side Trips

Kailua-Kona, Island of Hawaii

— 7 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.
Step off the beaten path and head to Hawaiian Vanilla Company and Waipiʻo Valley Lookout. Change things up with a short trip to Waialea Beach in Waimea (about 46 minutes away). There's still lots to do: relax in the rural setting at Hula Daddy Kona Coffee, take an unforgettable tour with a helicopter tour, take an in-depth tour of Hulihe'e Palace, and go for a stroll along the water at Honokohau Marina.

To find more things to do, other places to visit, and other tourist information, use the Kailua-Kona online trip maker.

Traveling by flight from Kihei to Kailua-Kona takes 2.5 hours. In January, daily temperatures in Kailua-Kona can reach 80°F, while at night they dip to 67°F. Wrap up your sightseeing on the 30th (Sun) to allow time to fly back home.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Tours

Side Trips

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.