28 days in Hawaii Itinerary

28 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

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

— 3 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: Pu'uhonua O Honaunau National Historical Park (in Honaunau), Puukohola National Historic Park (in Kawaihae) and Hapuna Beach State Recreation Area (in Puako). There's lots more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, see the interesting displays at Halualoa ukelele gallery, experience rural life at Heavenly Hawaiian Kona Coffee Farm, and play a few rounds at Mauna Lani Resort .

To find more things to do, maps, traveler tips, and other tourist information, you can read our Kailua-Kona trip planner.

Jacksonville to Kailua-Kona is an approximately 15-hour flight. The time zone changes from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST), which is usually a -5 hour difference. When traveling from Jacksonville in February, plan for somewhat warmer days and warmer nights in Kailua-Kona: temperatures range from 81°F by day to 69°F at night. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Hilo.

Things to do in Kailua-Kona

Outdoors · Parks · Beaches · Nature

Side Trips

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.
Venture out of the city with trips to Hawaii Volcanoes National Park (Kipuka Puaulu (Bird Park) Trail, Nature & Wildlife Tours, &more) and Jagger Museum (in Volcano). There's lots more to do: immerse yourself in nature at Akaka Falls State Park, take in the dramatic scenery at Rainbow Falls, see the sky in a new way at Imiloa Astronomy Center, and admire the natural beauty at Liliuokalani Gardens.

For photos, where to stay, more things to do, and tourist information, read Hilo trip planner.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. In February in Hilo, expect temperatures between 81°F during the day and 65°F at night. Cap off your sightseeing on the 8th (Mon) early enough to travel to Lahaina.

Things to do in Hilo

Parks · Outdoors · Museums · Trails

Side Trips

Lahaina, Maui

— 8 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.
Explore Lahaina's surroundings by going to Maui Veterans Cemetery (in Makawao), Haleakala Crater (in Haleakala National Park) and Wailuku (Hale Ho'ike'ike at the Bailey House & Iao Valley). Spend the 11th (Thu) 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, kick back and relax at Maluaka Beach, observe the fascinating underwater world at Maui Ocean Center, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To find photos, more things to do, ratings, and tourist information, read Lahaina tour itinerary planner.

Getting from Hilo to Lahaina by flight takes about 4.5 hours. In February in Lahaina, expect temperatures between 78°F during the day and 67°F at night. Finish up your sightseeing early on the 16th (Tue) so you can travel to Lihue.

Things to do in Lahaina

Outdoors · Parks · Beaches · Scenic Drive

Side Trips

Lihue, Kauai

— 3 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Change things up with these side-trips from Lihue: Waimea (Polihale State Park & Waimea Canyon State Park) and Na Aina Kai Botanical Gardens (in Kilauea). Next up on the itinerary: whizz through the canopy at some of the top local zipline courses and adventure parks, look for gifts at Kela's Glass Gallery, appreciate the extensive heritage of Kalalau Lookout, and take an unforgettable tour with a helicopter tour.

To see reviews and more tourist information, use the Lihue trip maker.

Getting from Lahaina to Lihue by flight takes about 4 hours. In February, daily temperatures in Lihue can reach 78°F, while at night they dip to 66°F. Wrap up your sightseeing on the 19th (Fri) early enough to travel to Honolulu.

Things to do in Lihue

Parks · Outdoors · Nature · Tours

Side Trips

Honolulu, Oahu

— 9 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.
Change things up with these side-trips from Honolulu: Haleiwa (Waimea Bay, Sunset Beach Park, &more), Kailua Beach Park (in Kailua) and Pu’u O Mahuka Heiau State Monument (in Pupukea). And it doesn't end there: explore the different monuments and memorials at USS Arizona Memorial, kick back and relax at Waikiki Beach, admire the sheer force of Manoa Falls, and explore the activities along Hanauma Bay Nature Preserve.

Before you visit Honolulu, use our trip planner to discover what you can do and see there.

You can fly from Lihue to Honolulu in 2.5 hours. In February in Honolulu, expect temperatures between 81°F during the day and 69°F at night. Cap off your sightseeing on the 28th (Sun) early enough to travel back home.

Things to do in Honolulu

Parks · Outdoors · 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.