32 days in Hawaii Itinerary

32 days in Hawaii Itinerary

Created using Inspirock Hawaii route planner

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

— 4 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.
Change things up with these side-trips from Hilo: Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Volcano Art Center Gallery, Kilauea Iki Trailhead, &more). Next up on the itinerary: admire the sheer force of Akaka Falls State Park, see the interesting displays at Pacific Tsunami Museum, admire the natural beauty at Liliuokalani Gardens, and head off the coast to Coconut Island.

To find maps, where to stay, other places to visit, and tourist information, use the Hilo trip itinerary tool.

Las Vegas to Hilo is an approximately 10-hour flight. You'll gain 2 hours traveling from Las Vegas to Hilo due to the time zone difference. Expect slightly colder weather when traveling from Las Vegas in May: highs in Hilo hover around 82°F, while lows dip to 67°F. Finish your sightseeing early on the 12th (Wed) so you can drive to Kailua-Kona.

Things to do in Hilo

Parks · Museums · Outdoors · Wildlife

Side Trips

Find places to stay May 8 — 12:
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Kailua-Kona, Island of Hawaii

— 5 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.
Change things up with these side-trips from Kailua-Kona: Puukohola National Historic Park (in Kawaihae), Captain Cook (Big Island Bees & Kealakekua Bay) and Hapuna Beach State Recreation Area (in Puako). And it doesn't end there: get close to the beloved marine mammals with a swim-with-the-dolphins experience, tee off at Mauna Lani Resort , explore the fascinating underground world of Kula Kai Caverns, and take an in-depth tour of Kona Coffee Living History Farm.

To find traveler tips, reviews, ratings, and other tourist information, you can read our Kailua-Kona trip itinerary maker website.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. Traveling from Hilo in May, expect a bit warmer with lows of 73°F in Kailua-Kona. Finish your sightseeing early on the 17th (Mon) to allow enough time to fly to Lahaina.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay May 12 — 17:
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Lahaina, Maui

— 7 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.
Venture out of the city with trips to Makawao (Maui Veterans Cemetery & Ho'omana Spa Maui), Haleakala Crater (in Haleakala National Park) and Kalepolepo Beach Park (in Kihei). Spend the 24th (Mon) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: see some colorful creatures with a scuba or snorkeling tour, hit the best photo ops around with an inspiring photography tour, enjoy the sand and surf at Napili Beach, and admire the majestic nature at Iao Valley.

For photos, where to stay, ratings, and other tourist information, go to the Lahaina trip builder site.

Getting from Kailua-Kona to Lahaina by flight takes about 2.5 hours. In May, plan for daily highs up to 81°F, and evening lows to 70°F. Wrap up your sightseeing on the 24th (Mon) early enough to fly to Lihue.

Things to do in Lahaina

Outdoors · Parks · Beaches · Scenic Drive

Side Trips

Find places to stay May 17 — 24:
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Lihue, Kauai

— 5 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Get out of town with these interesting Lihue side-trips: Waimea (Aunty Liliko'i, Waimea Canyon State Park, &more), Na Aina Kai Botanical Gardens (in Kilauea) and Kekaha (Boat Tours & Water Sports & Kokee Natural History Museum). There's much more to do: tour the pleasant surroundings at Na Pali Coast State Park, take in nature's colorful creations at Limahuli Garden and Preserve, enjoy the sand and surf at Poipu Beach Park, and admire all the interesting features of Sleeping Giant Trail.

For where to stay, photos, and tourist information, you can read our Lihue tour itinerary builder website.

Traveling by flight from Lahaina to Lihue takes 2.5 hours. In May, daily temperatures in Lihue can reach 82°F, while at night they dip to 71°F. Finish your sightseeing early on the 29th (Sat) to allow enough time to fly to Honolulu.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay May 24 — 29:
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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.
Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Pupukea Beach Park, Sunset Beach Park, &more). There's lots more to do: trek along Diamond Head State Monument, admire the sheer force of Manoa Falls, admire the masterpieces at Honolulu Museum of Art, and see some colorful creatures with a scuba or snorkeling tour.

For more things to do and tourist information, read Honolulu road trip planning tool.

Traveling by flight from Lihue to Honolulu takes 2.5 hours. In May, daytime highs in Honolulu are 84°F, while nighttime lows are 71°F. On the 8th (Tue), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in Honolulu

Outdoors · Parks · Beaches · Museums

Side Trips

Find places to stay May 29 — Jun 8:
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Hawaii travel guide

4.4
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.