29 days in Hawaii, Island of Hawaii & Maui Itinerary

29 days in Hawaii, Island of Hawaii & Maui Itinerary

Created using Inspirock United States trip planner
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Fly
1
Lihue, Kauai
— 3 nights
Fly
2
Honolulu, Oahu
— 9 nights
Fly
3
Hilo
— 4 nights
Drive
4
Waikoloa
— 3 nights
Fly
5
Wailuku
— 1 day
Drive
6
Lahaina
— 9 nights
Fly

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Lihue, Kauai — 3 nights

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Step off the beaten path and head to Kauai Path and Queen's Bath. Change things up with a short trip to Pali Ke Kua Beach (Hideaway s Beach) in Princeville (about 56 minutes away). Next up on the itinerary: kick back and relax at Kalapaki Beach, relax and rejuvenate at some of the best spas, stroll through Secret Beach, and trek along Kuilau Ridge Trail.

For more things to do, traveler tips, reviews, and other tourist information, go to the Lihue journey planner.

Los Angeles to Lihue is an approximately 7.5-hour flight. Traveling from Los Angeles to Lihue, you'll gain 2 hours due to the time zone difference. Expect somewhat warmer evenings in Lihue when traveling from Los Angeles in June, with lows around 73°F. Cap off your sightseeing on the 5th (Sat) early enough to catch the flight to Honolulu.
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Outdoors · Parks · Trails · Beaches
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.
You'll explore the less-touristy side of things at Photography Tours and Food Tours. Venture out of the city with trips to Waimanalo Beach (in Waimanalo), Kailua (Kailua Beach Park, Pillbox Hike, &more) and Byodo-In Temple (in Kaneohe). Next up on the itinerary: look for all kinds of wild species at Wildlife Areas, stroll around Fort DeRussy Beach Park, go for a walk through Diamond Head State Monument, and contemplate the waterfront views at Hanauma Bay Nature Preserve.

To find traveler tips, ratings, other places to visit, and other tourist information, you can read our Honolulu trip itinerary planning tool.

Traveling by flight from Lihue to Honolulu takes 2.5 hours. In June in Honolulu, expect temperatures between 86°F during the day and 74°F at night. Finish up your sightseeing early on the 14th (Mon) so you can catch the flight to Hilo.
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Parks · Outdoors · Beaches · Tours
Side Trips

Hilo — 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.
You'll explore the less-touristy side of things at Kilauea Iki Trailhead and Richardson Beach Park. Venture out of the city with trips to Hawaii Volcanoes National Park (Devastation Trail & Holei Sea Arch), Kula Kai Caverns (in Ocean View) and Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz (in Naalehu). There's still lots to do: head off the coast to Coconut Island, examine the collection at Pacific Tsunami Museum, cruise along Chain of Craters Rd, and get interesting insight from Tours.

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

Fly from Honolulu to Hilo in 2.5 hours. Traveling from Honolulu in June, you can expect nighttime temperatures to be little chillier in Hilo, with lows of 69°F. Finish your sightseeing early on the 18th (Fri) to allow enough time to drive to Waikoloa.
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Parks · Outdoors · Nature · Beaches
Side Trips

Waikoloa — 3 nights

Waikoloa Village is a census-designated place (CDP) in Hawaii County, Hawaii, United States. Kick off your visit on the 19th (Sat): contemplate the long history of Puukohola National Historic Park, then contemplate the waterfront views at Puako Bay, and then play a few rounds at Waikoloa Village Golf Club. On the 20th (Sun), you'll have a packed day of sightseeing: get interesting insight from Dolphin Quest, tour the pleasant surroundings at Waikoloa Petroglyph Preserve, and then get a taste of life in the country at Dahana Ranch.

For photos, other places to visit, maps, and other tourist information, go to the Waikoloa online holiday maker.

You can drive from Hilo to Waikoloa in 1.5 hours. Alternatively, you can drive; or take a bus. In June, plan for daily highs up to 85°F, and evening lows to 74°F. Finish your sightseeing early on the 21st (Mon) so you can fly to Wailuku.
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Outdoors · Parks · Golf · Wildlife
Side Trips

Wailuku — 1 day

Wailuku is a census-designated place (CDP) in Maui County, Hawaii, United States. On the 21st (Mon), observe the fascinating underwater world at Maui Ocean Center, discover the deep blue sea with Maui Reef Adventures, and then get engrossed in the history at Story of Hawaii Museum.

To find ratings, more things to do, maps, and more tourist information, read Wailuku online travel planner.

You can fly from Waikoloa to Wailuku in 2.5 hours. In June, daytime highs in Wailuku are 87°F, while nighttime lows are 71°F. Cap off your sightseeing on the 21st (Mon) early enough to go by car to Lahaina.
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Wildlife · Outdoors · Tours · Zoos & Aquariums
Side Trips

Lahaina — 9 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 explore the less-touristy side of things at Zipline and Kayaking & Canoeing. Next up on the itinerary: look for all kinds of wild species at Honolua Bay, see Off-Road Tours, experience rural life at Punakea Palms, and contemplate the waterfront views at Lahaina Harbor.

For more things to do, other places to visit, traveler tips, and more tourist information, you can read our Lahaina trip maker app.

Getting from Wailuku to Lahaina by car takes about an hour. Other options: take a bus. In June, plan for daily highs up to 84°F, and evening lows to 72°F. You will have some time to spend on the 30th (Wed) before leaving for home.
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Outdoors · Parks · 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.
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Island of Hawaii travel guide

4.5
Scuba & Snorkeling · Swim with Dolphins · Beaches
The Big Island
Aptly nicknamed the "Big Island," the Island of Hawaii features sunny, black-sand beaches on the western side by Kona and a tropical rain forest on the eastern by Hilo. In between, the massive mountain Maunaloa covers half the island, and Kilauea, one of the world's most active volcanoes, erupts continuously. Twice as large as all the other Hawaiian Islands combined, this big chunk of land in the Pacific manages to retain a laid-back atmosphere despite its immense popularity with tourists. Instead of spending your entire vacation at one of the island's luxurious tourist resorts, go on tours of this Pacific haven's coffee and macadamia nut plantations and working ranches, or explore its nature reserves and rugged trails.
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Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Zipline
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.
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