31 days in Hawaii Itinerary

31 days in Hawaii Itinerary

Created using Inspirock Hawaii holiday maker

Make it your trip
Fly
1
Lahaina, Maui
— 6 nights
Fly
2
Hilo, Island of Hawaii
— 5 nights
Drive
3
Kailua-Kona, Island of Hawaii
— 4 nights
Fly
4
Lihue, Kauai
— 5 nights
Fly
5
Honolulu, Oahu
— 10 nights
Fly

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Lahaina, Maui

— 6 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.
You'll find plenty of places to visit near Lahaina: The Awakening Church (in Kihei), Haleakala Crater (in Haleakala National Park) and Iao Valley (in Wailuku). Spend the 2nd (Sun) exploring the striking scenery along Hana Highway - Road to Hana. There's lots more to do: discover the deep blue sea with a scuba or snorkeling tour, kick back and relax at Wailea Beach, stroll around Lahaina Banyan Court, and tour the pleasant surroundings at Kapalua Beach.

To see more things to do, other places to visit, where to stay, and other tourist information, use the Lahaina trip itinerary maker site.

Cleveland to Lahaina is an approximately 14-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST) is minus 5 hours. Prepare for a bit warmer weather when traveling from Cleveland in May: high temperatures in Lahaina hover around 81°F and lows are around 70°F. Wrap up your sightseeing on the 7th (Fri) to allow time to travel to Hilo.

Things to do in Lahaina

Parks · Outdoors · Beaches · Scenic Drive

Side Trips

Hilo, Island of Hawaii

— 5 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.
Get out of town with these interesting Hilo side-trips: Hawaii Volcanoes National Park (Volcano Art Center Gallery, Kilauea Iki Trailhead, &more) and Jagger Museum (in Volcano). There's still lots to do: take in the dramatic scenery at Akaka Falls State Park, get up close and personal with brilliant marine life at Mokupapapa Discovery Center, see the sky in a new way at Imiloa Astronomy Center, and take an unforgettable tour with a helicopter tour.

For ratings, reviews, where to stay, and tourist information, go to the Hilo trip planner.

You can fly from Lahaina to Hilo in 4.5 hours. In May in Hilo, expect temperatures between 82°F during the day and 67°F at night. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Museums · Wildlife

Side Trips

Kailua-Kona, Island of Hawaii

— 4 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.
You'll find plenty of places to visit near Kailua-Kona: Kealakekua Bay (in Captain Cook), Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Papakōlea Green Sand Beach (in Naalehu). There's lots more to do: take a tour by water with Boat Tours & Water Sports, kick back and relax at Mauna Kea Beach, head outdoors with Aloha Rail Company, and relax in the rural setting at The Vanillerie.

To find reviews and other tourist information, read our Kailua-Kona travel itinerary planner.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. Traveling from Hilo in May, you can expect nighttime temperatures to be somewhat warmer in Kailua-Kona, with lows of 73°F. Finish your sightseeing early on the 16th (Sun) so you can travel to Lihue.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

Side Trips

Lihue, Kauai

— 5 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Venture out of the city with trips to Na Aina Kai Botanical Gardens (in Kilauea), Waimea (Aunty Liliko'i, Waimea Canyon State Park, &more) and Boat Tours & Water Sports (in Kekaha). There's much more to do: immerse yourself in nature at Na Pali Coast State Park, contemplate the long history of Kilohana, see the world from above with a helicopter tour, and play a few rounds at Poipu Bay Resort Golf Course.

To see traveler tips, more things to do, ratings, and other tourist information, read our Lihue trip builder tool.

Getting from Kailua-Kona to Lihue by flight takes about 2.5 hours. In May in Lihue, expect temperatures between 82°F during the day and 71°F at night. Finish your sightseeing early on the 21st (Fri) so you can travel to Honolulu.

Things to do in Lihue

Parks · Outdoors · Tours · Beaches

Side Trips

Honolulu, Oahu

— 10 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.
Explore Honolulu's surroundings by going to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Ehukai Pillbox Hike, Sunset Beach Park, &more). There's still lots to do: tour the pleasant surroundings at Diamond Head State Monument, make a trip to Polynesian Cultural Center, take in the dramatic scenery at Manoa Falls, and admire the masterpieces at Honolulu Museum of Art.

To see reviews, ratings, photos, and other tourist information, refer to the Honolulu tour planner.

Traveling by flight from Lihue to Honolulu takes 2.5 hours. In May in Honolulu, expect temperatures between 84°F during the day and 71°F at night. Cap off your sightseeing on the 31st (Mon) early enough to travel back home.

Things to do in Honolulu

Parks · Outdoors · Museums · Beaches

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.