Hawaii Itinerary: The Two-Week All-Island Trip

Hawaii Travel Itinerary - The Two-Week All-Island Trip

You can be forgiven for thinking that the islands are all the same. They’re so close to each other and so isolated in the middle of the Pacific. How much could they differ? In fact, each island has its own unique personality, its own geography, plant and bird life, culture, activities, historical sites—and opportunities for new experiences. It’s possible to see the best of all the islands in two weeks. If you have more time, follow the advice below to extend your stay to three weeks for full immersion in island living.

Getting between the islands is a quick flight: thirty minutes at most. O‘ahu, Maui, the Big Island, and Kaua‘i all have airports servicing international, national, and interisland carriers. So with proper planning, you can begin a multi-week itinerary from any island. However, most national and international flights travel through Honolulu International Airport, so O‘ahu makes a great starting point. Whichever islands you’re visiting, it’s easy to spend an extra day or two on O‘ahu at the beginning or end of your trip.

Getting between the islands is a quick flight: thirty minutes at most. Flight time across the entire state, tip to tip from the Big Island to Kaua‘i, is about ninety minutes, although many flights stop for a quick layover on O‘ahu. Car rental companies are located at all major airports and each island has ample accommodations. You’ll have to pack up camp and get re-situated with each island hop, but it’s a small price for enjoying the diversity of the islands.

Map of Hawaii's Inter-Island Air Routes

Inter-Island Air Routes


Day 1

After arriving on O‘ahu, you’ll most likely head straight to Waikiki, where most of the island’s accommodations are located. Acclimate by swimming and relaxing on the beach. If you’re ready for something more active, take surf lessons, go for an outrigger canoe ride, or hike the Diamond Head crater. Treat yourself to a delicious meal at Duke’s Waikiki or Sansei Seafood Restaurant and Sushi Bar and get a good night’s rest to adjust for any time difference.

Famous Waikiki beach with Diamond Head in the distance.

Famous Waikiki Beach with Diamond Head in the distance. Photo © Christopher Howey/123rf.

Day 2

Venture out and explore. Head to the Pearl Harbor historic sites, getting there early to beat the crowd. Heading back into Downtown Honolulu, visit the Historic and Capitol District, where museums and historic buildings abound. End the afternoon with some relaxing beach time. That evening, walk to Chinatown, just a few blocks away, and take in the burgeoning art and food scene. Restaurants, bars, clubs, markets, shops, and art galleries line the streets. Sample the culinary diversity with pizza and beer at J.J. Dolan’s, Chinese at Little Village Noodle House, or try Middle Eastern fare at Kan Zaman.

Day 3

After breakfast, hop on the freeway and over to the windward side for one of the prettiest drives on the island. Take the coast highway up the windward side to the North Shore. If it’s winter, relax at the beach and check out the waves. If it’s summer, get in the water and snorkel. Sharks Cove, Three Tables, and Waimea Bay have the most marine life, but will also be the most crowded. Head back through historic Hale‘iwa town where you can shop, eat and drink. Haleiwa Joe’s is one of the best restaurants on the North Shore. And don’t miss the legendary Matsumoto Shave Ice.

Extend Your Stay

If you have a few more days to spend on O‘ahu, pack your bags and relocate to the North Shore. Consider a stay at Turtle Bay Resort or a vacation rental along the North Shore beaches, where you can really immerse yourself in the beauty of the area. Or stay put in your Waikiki hotel, using it as a base to visit the southeast corner of the island, from Hawai‘i Kai to Kailua. Water activities abound in Maunalua Bay, with surf schools, fishing and dive charters, and recreational boating. Koko Crater is home to a dryland botanical garden, there are hikes from Makapu‘u to Kailua. Yokohama Bay, at the end of the road on the leeward side, is one of the most pristine and uncrowded spots on the island. It’s also the starting point of a hike to Ka‘ena Point, where a natural preserve is home to monk seals and seabirds.

Big Island of Hawai‘i

Day 4

You’re Big Island bound! If ocean recreation is your priority, fly into Kailua Kona and set up a home base on the leeward side. If the volcanoes are your focus, base yourself in Hilo. Long driving distances separate the coasts, so you’ll need to relocate your accommodations from one side to the other and plan your time wisely to see the whole island. Get an early start by exploring the beautiful waters and town of Kailua-Kona. No trip to the area is complete without a visit to the Captain Cook Monument and Kealakekua Bay State Historical Park, which can also serve as a starting point for a kayaking tour. In the afternoon, visit Pu‘uhonua O Honaunau National Historical Park to get a glimpse of ancient Hawaii at this safe haven for defeated chiefs and kapu-breakers, then explore the coffee plantations and tasting rooms around Kona. Or relax near your hotel, taking advantage of the sunshine.

View of Hilo and the countryside from the edge of the bay.

Hilo’s weather makes it a natural greenhouse; botanical gardens and flower farms surround Hilo like a giant lei. Photo © David Fulmer, licensed Creative Commons Attribution.

Day 5

Drive north to the Kohala Coast, stopping to enjoy the white sands of Hapuna Beach or the Puako tide pools, one of the best snorkeling spots on the island. In the afternoon, head inland to the upcountry paniolo town of Waimea. Dine at Merriman’s Market Café, one of the originators of Hawaii Regional Cuisine. Or head back to the coast to Kawaihae for dinner and dancing at Blue Dragon Coastal Cuisine & Musiquarium. Another option is a prearranged guided tour to the top of Mauna Kea for sunset and star gazing. Stay the night on the Kohala Coast.

Day 6

Take a scenic drive to beautiful Waipi‘o Valley. Arrange for a scenic tour of the valley or hike down if you’re adventurous. Drive along the Hamakua Coast, stopping at Onomea Bay, where a short trail leads down to a beautiful cove. Then drive into Hilo for the farmers market followed by dinner. Try delicious and popular Café Pesto. Stay the night in Hilo.

Day 7

Today is all about Hawai‘i Volcanoes National Park. After about an hour drive from Hilo, you’ll enter the park, where you can explore the visitor’s center, lava fields, drive around and view and active volcano, and hike through lava tubes and native Hawaiian forests. After a full day in the park, enjoy food and art in Volcano Village before heading back to your hotel in Hilo.

Extend Your Stay

It’s easy to extend a stay on the big island. Just hang tight for more in-depth exploration in the region of your choice. Add a day trip over the Saddle Road between Mauna Kea and Mauna Loa. Or spend more time in Hawai‘i Volcanoes National Park, staying overnight at quaint lodgings in Volcano Village for a full two or more days of exploration.

Mountain tops peek out above a sea of clouds as the sun rises and paints the sky brilliant colors.

A beautiful mountain top sunrise in Maui’s Haleakala National Park. Photo © Max Earey/123rf.

Maui, Lana‘i, and Moloka‘i

Day 8

A change of scenery is in store on Maui, where long stretches of beautiful sandy beaches are the main draw. Stay along in Kihei on the south side or around Ka‘anapali on the west side. Greet Maui by soaking up the sun at D.T. Fleming Beach Park or Keawakapu Beach. Enjoy the refreshing water and take a long sunset stroll.

Day 9

Head upcountry and visit Haleakala, a dormant volcano that dominates all of the views on the island. Drive to the top and hike around, or take a biking tour of the area. Guides can take you to the top to witness sunrise above the clouds, then cycle with you along the windy road down the mountain and through green pastures. Break up your ride with a stop in the upcountry town of Kula. Afterwards, check out Pa‘ia, enjoying food and drink at Charley’s or Mama’s Fish House. Or head to the old whaling town of Lahaina to explore island history and enjoy dinner at Lahaina Grill or Koa’s Seaside Grill.

Day 10

Take a snorkeling, scuba diving, fishing, or whale-watching tour. Tour operators leave from Lahaina, Ma‘alaea Harbor and Ka‘anapali. You can select snorkeling and diving tours to Molokini, Lana‘i, Moloka‘i, and up and down Maui’s coast. Molokini is a must see, but make sure to get the early boat to avoid the crowds. If a secluded beach day is more to your liking, take the ferry to Moloka‘i or Lana‘i for the day.

Day 11

Today is the day: Road to Hana. Start off as early as possible. The drive takes at least three hours (from the beginning, just past Ho‘okipa) and you’ll want to make lots of stops along the way. Take your time. Hike to waterfalls, eat at a roadside fruit stand, and take lots of pictures. Visit a heiau and botanical gardens in Hana, grab lunch from the general store, and find a nook on Pa‘iloa Beach to relax and take it all in.

Mist above waterfall on the Road to Hana, Maui, Hawaii.

The Road to Hana is Maui’s most popular attraction: a winding drive to a sleepy town in a lush setting. Photo © iofoto/123rf.

Extend Your Stay

If you extend your stay on Maui, take the time to enjoy the island at a slower pace. Spend the night in Hana to break up the drive over two days. Or plan on longer side trips to Moloka‘i and Lana‘i, which are easiest to do from Maui. Or enjoy more beach time at your resort or vacation rental.


Day 12

On Kaua‘i, choose either the North Shore or South Shore as a home base. The South Shore is much sunnier, while the North Shore is lush due to frequent showers. Begin with a beach day at Po‘ipu. The National Tropical Botanical Garden and Spouting Horn blowhole nearby are available for exploration. The quaint town of Koloa is a perfect place to grab lunch. After lunch, head into Lihue for a stop at the Kaua‘i Museum and dinner at Duke’s on Kalapaki Beach or Gaylord’s at the Kilohana Plantation.

Day 13

Wake early and drive to Waimea Canyon, where amazing photo-ops await at the lookout. If you’re the adventurous type, take a hike in forested Koke‘e State Park. On the way back to your hotel, stop in historic Waimea town and Hanapepe, full of art galleries and curious shops and eateries.

Day 14

Time to explore the North Shore, one of the most beautiful places in all the state. Take your beach gear. Stop at the lighthouse in Kilauea and see the wildlife refuge, where seabirds nest in the cliffs. Continue on to Hanalei Bay, filled with shops and eateries. The perfect half-moon beach is great for surfing or stand-up paddling. After lunch in Hanalei, head north to the end of the road at Ke‘e Beach. Swim, relax, and head to must-see Limahuli Botanical Garden when you need a break from the sun.

The beach at Hanalei Bay. Photo © Kimi Owens.

The beach at Hanalei Bay. Photo © Kimi Owens.

Extend Your Stay

Plan on splitting your time with a few days on both the North and South Shores to fully experience each region to its fullest. Spend an extra day taking a helicopter tour of Waimea Canyon and the inaccessible Na Pali Coast or a boat tour of the Na Pali Coast.

Excerpted from the First Edition of Moon Hawaiian Islands.

Leave a Reply

Your email address will not be published. Required fields are marked *


  1. iamandoni says:

    Hi Kevin,

    Thanks for this post.

    How much it’s gonna cost for that trip ?

    Many thanks in advance

    • Kimi Owens (admin) says:

      All the pricing information for the locations that Kevin suggests are available in his travel guide (Moon Hawaiian Islands)! Because this itinerary is meant for a range of budgets (tighter budgets might opt to stay in a rental and cook meals vs stay at a resort, for example) there is no ballpark. Personally, when budgeting for a trip, I start with airfare/car rental, lodging, food and key activities in the length of time I would like to stay, and then adjust where needed to fit my budget.

  2. izhar finkelstein says:

    My wife and I looking for an organized group tour of 2 weeks in the islands of Hawaii. Starting date around Sep 22, 2016 can you recommend us a tour company?

    • Kimi Owens (admin) says:

      Hi Izhar,

      Our books are geared towards independent travelers who are seeking to plan their own adventures, so guided tours are more commonly recommended than organized tours. While in some destinations our authors may have recommendations for organized tours or treks, we don’t have any for Hawaii. You might try browsing the official tourism agency site for companies offering group tours: http://www.gohawaii.com/

  3. John Reid says:

    Kevin, my wife and I are planning a trip to Hawaii for our 25th wedding anniversary in May 2015. 8-10 days, two islands. Any suggestions for an itinerary (places to visit, eat, stay etc.)?
    John Reid

    • Kimi Owens (admin) says:

      Hi John,

      If the itineraries on this page aren’t enough to get you started, Kevin has some great suggestions for “island pairings” in his book that can help you get an idea of which two islands might make for the best trip for you and your wife.