28 days in Hawaii Itinerary

28 days in Hawaii Itinerary

Created using Inspirock Hawaii journey planner
Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 4 nights
Drive
2
Hilo, Island of Hawaii
— 3 nights
Fly
3
Lahaina, Maui
— 7 nights
Fly
4
Koloa, Kauai
— 5 nights
Fly
5
Honolulu, Oahu
— 8 nights
Fly

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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.
Explore the numerous day-trip ideas around Kailua-Kona: Hapuna Beach State Recreation Area (in Puako), Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Puukohola National Historic Park (in Kawaihae). And it doesn't end there: get close to the beloved marine mammals with a swim-with-the-dolphins experience, experience rural life at Heavenly Hawaiian Kona Coffee Farm, tee off at Mauna Lani Resort , and get great views at Pololu Valley Lookout.

For reviews, maps, photos, and other tourist information, read Kailua-Kona vacation website.

San Diego to Kailua-Kona is an approximately 7.5-hour flight. The time zone changes from Pacific Standard Time (PST) to Hawaii-Aleutian Standard Time (HST), which is usually a -2 hour difference. In September, Kailua-Kona is a bit warmer than San Diego - with highs of 87°F and lows of 76°F. Cap off your sightseeing on the 2nd (Sun) early enough to go by car to Hilo.
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Parks · Outdoors · Beaches · Nature
Side Trips

Hilo, Island of Hawaii — 3 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). It doesn't end there: admire the natural beauty at Liliuokalani Gardens and take in the dramatic scenery at Akaka Falls State Park.

To find more things to do, other places to visit, where to stay, and tourist information, read Hilo online travel route builder.

You can drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in October, Hilo is a bit cooler at night with lows of 70°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to fly to Lahaina.
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Parks · Outdoors · Trails · Nature
Side Trip

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.
Change things up with these side-trips from Lahaina: Ho'okipa Beach Park (in Paia), Makawao (Ho'omana Spa Maui & Maui Veterans Cemetery) and Iao Valley (in Wailuku). Spend the 6th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: discover the deep blue sea with a scuba or snorkeling tour, kick your exploration up a notch at some of the top local zipline courses and adventure parks, enjoy the sand and surf at Ka'anapali Beach, and walk around Lahaina Banyan Court.

To find photos, other places to visit, more things to do, and tourist information, read Lahaina trip itinerary planning site.

Traveling by flight from Hilo to Lahaina takes 2.5 hours. October in Lahaina sees daily highs of 84°F and lows of 73°F at night. Finish your sightseeing early on the 12th (Wed) so you can fly to Koloa.
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Outdoors · Parks · Beaches · Scenic Drive
Side Trips

Koloa, Kauai — 5 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Venture out of the city with trips to Waimea (Waimea Canyon State Park, Koke'e Mountains, &more), Na Pali Coast State Park (in Wainiha) and Hanalei (Hanalei Valley Lookout & Hanalei Beach). There's still lots to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, see the world from above with a helicopter tour, enjoy the sand and surf at Tunnels Beach, and surround yourself with nature on Kauai Safaris.

For reviews, where to stay, other places to visit, and more tourist information, read our Koloa holiday planning app.

You can fly from Lahaina to Koloa in 2.5 hours. In October, plan for daily highs up to 84°F, and evening lows to 74°F. Finish your sightseeing early on the 17th (Mon) so you can fly to Honolulu.
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Parks · Outdoors · Nature · Tours
Side Trips

Honolulu, Oahu — 8 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 Haleiwa (Sunset Beach Park & Waimea Bay), Turtle Bay Golf (in Kahuku) and Kailua (Kailua Beach Park & Lanikai Beach). Next up on the itinerary: explore the different monuments and memorials at USS Arizona Memorial, contemplate the long history of Battleship Missouri Memorial, capture your vacation like a pro with an inspiring photography tour, and identify plant and animal life at Wildlife Areas.

To see photos, other places to visit, traveler tips, and more tourist information, read Honolulu travel route builder website.

Traveling by flight from Koloa to Honolulu takes 2.5 hours. October in Honolulu sees daily highs of 87°F and lows of 74°F at night. On the 25th (Tue), wrap the sightseeing up by early afternoon so you can fly back home.
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Outdoors · Parks · Beaches · Historic Sites
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.
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