Itinerary map here

The major Hawaiian Islands in 14 days

4 nights: Oahu for a perfect mix of history, culture, food and natural beauty of the Hawaiian Islands, including Pearl Harbor, Iolani Palace, Waikiki Beach, North Shore shrimp trucks, Lanikai Beach, Makapu’u Lighthouse, Halona Blow Hole, and Sandy’s Beach.
4 nights: Big Island for the Volcanoes National Park, Mauna Kea Observatory, snorkeling at the “Two-Step”, Black Sand Beach, Kona coffee, Macadamia nuts and Kona beer.
3 nights: Maui for Makena Beach, Mt. Haleakala, sunrise diving at Molokini, whale-watching in the Spring, Road to Hana, and tropical night life on Lahaina.
1 day/0 night: Lanai for Hulopoe Beach, Sweetheart Rock, Shipwreck beach, Garden of the Gods, and Lanai pineapple.
2 nights: Kauai for Napali Coast, Waimea Canyon, Poipu Beach, Princeville and Hanalei.

" This is the perfect itinerary to discover the major islands of Hawaii including Oahu, Big Island, Maui, Lanai and Kauai in two weeks only. Be ready for some island hopping fun! "

Some general information:

The best to travel within an island is to rent a car. To travel in between islands, book flight tickets in advance.



4 nights


Oahu is the perfect mix of urban and island life and the gateway to the history, culture, food and natural beauty of the Hawaiian Islands. For history and cultural buffs, you will enjoy visits to Pearl Harbor, the state Capitol, Iolani Palace and other historical landmarks. For foodies and party goers, Oahu has the most restaurants, waterholes and clubs of any other Hawaiian island. For nature lovers, there are miles of pristine beaches and hiking trails to explore, tons of golf courses and kayak opportunities. For surfing addicts, come in December to March where you may catch 20+ feet monster waves on Oahu’s famed North Shore.

What to do:

Day 1 (Waikiki and Downtown Honolulu) - Arrive, pick up rental car (a necessity in Hawaii!), get and settle in.

In downtown Honolulu, you will find Iolani Palace, the only royal palace in the U.S., the Supreme Court of Hawaii with the golden statue of King Kamehameha in front, State Capitol with the statue of St. Damien and the Eternal Flame to commemorate the service men of Hawaii, Kawaiahao Church, the Westminister Abbey of Hawaii, and Honolulu City Hall (best during its annual Christmas lights and sculptures show). They are all in one strip on King Street, so it’s easy to hit all of them on a casual stroll. Break for lunch. Drive to the Roundtop for panoramic views of Honolulu.

Depending on the time you get in, you may be able to squeeze in a 30-minute hike up to the summit of Diamond Head for gorgeous, panoramic views of world-famous Waikiki Beach, the iconic, crescent-shaped beach of Hawaii. Take a leisurely stroll through the Waikiki beachfront towards Ala Moana, popping into cute souvenir shops that dot the main drag of Kalakaua Ave or pop your towel down on a section of the beach whenever you get tired. The sand behind the Moana Surfrider Hotel is so fine that you won’t be able to stop digging your toes into the finest white powder ever, or try Kahanamoku Beach, a peaceful lagoon, on the beachside of the Hilton Hawaiian Village. If you want to try out surfing, surfboard rentals and surfing lessons are offered right on the beach. Stop for happy hour/sunset drinks on the beachfront or in an ocean cruise, followed by dinner at one of the numerous options in Waikiki. If you are artistically inclined, art galleries open their doors for an evening of gallery walks around historic Chinatown on the first friday of each month.

Day 2 (East Oahu) - Snorkel at Hanauma Bay for half a day (open everyday except Tuesdays). Be sure to get there by 8am or 8:30am because 1) the parking lot will be full by 9 or 10 am and you will have to park really far away, and 2) the water is clearer early in the morning so you will be able to see more fish. You can buy your own or rent snorkeling gear at the beach.

Take lunch break at Koko Marina Shopping Center, where Kona Brewing Company serves up a delicious pint of coconut-flavored locally-brewed beer. Drive east along the picturesque Kalanianaole Highway towards the Halona Blowhole, where you will love the spray of the ocean mist on your face as the water squirts out in a glorious gush and spills onto the rocks. DO NOT go over the guardrails near the blowhole itself as the rocks can be slippery. Next to the blowhole, there’s a romantic little hidden gem of a beach dubbed the Eternity Beach where the movie, From Here to Eternity, was shot. Hike a few short steps down to the small, secluded beach and you will be the envy of all the blowhole onlookers. Continue to drive to Sandy’s Beach for top-notch waves and join in the boogie boarders! But watch for surf advisory signs as the waves at Sandy’s are extremely strong, so tighten that swim suit! Also a great spot to fly kites as the wind is very strong here. Alternatively, if you’ve had enough water for the day, hike the 1000+ stairs straight up Koko Head Crater for sunset views of East Oahu.

Day 3 (Kailua and Kaneohe) - Drive east along Kalanianaole Highway and do an easy, morning hike to Makapu’u Light House for rewarding views and possible humpback whale sightings from December to March. Enjoy the spectacular Koolau mountain range on your left and the gorgeous beaches on your right as you drive towards Waimanalo Beach, Bellows Beach Park, or Kailua Beach Park, all family-friendly beaches with pine tree shades, showers and picnic areas. If you see a sign for “Huli-Huli Chicken” on the roadside, do stop and thank your lucky stars that the stand is open. Best BBQ chicken ever--Hawaiian style. After you are delightfully fed, you will be ready to hit Lanikai Beach, the most beautiful beach on Oahu--or anywhere for that matters--where two small islets, Moku Nui and Moku Iki, juts out from aqua blue waters in the background. You can rent a kayak to get to these islets or rent a SUP (stand up paddleboard) to enjoy the calm blue waters. Stop for lunch in Kailua Town where there are tons of restaurants serving anything from fish tacos to burgers or plate lunch, a local favorite. On the drive back, visit the Pali Lookout for spectacular views of Kailua and Kaneohea (bring for jacket for the gusty Pacific winds up there).

Day 4 (Pearl Harbor and North Shore) - Visit Pearl Harbor to witness first-hand the destruction that lead to America joining World War II and the US Missouri Battleship to see the kind of big gun that helped America to win the fight.

Drive to Haleiwa, a quaint surfer town on Oahu’s North Shore. Get shave ice at Matsumoto’s, a local favorite for the better half of the last century. Get a late lunch at one of the famous shrimp trucks on the north shore: Giovanni’s or Fumi’s. In the winter months, check out monster waves at Pipeline Bonzai or Sunset Beach and try to attend one of the pipeline surfing competitions come November to December. Reserve the afternoon for golf, either at the ritzy Turtle Bay Golf Course or the cheap, local alternative, Kahuku Golf Course, which has equally nice ocean views for a fraction of the price.

Additional tips:

Hike through the tropical rainforest for the opportunity to splash into a tropical waterfall at Manoa Falls or Maunawili Falls.

For shoppers, check out Ala Moana Shopping Center, the biggest outdoor shopping mall in the world and just next door to Waikiki, Waikele Outlet Mall for name-brand bargains, and Aloha Stadium for cheap souvenirs on swap meet days on Wednesdays and weekends. For families with kids, Sea Life Park, which offers dolphin shows, is across the street and is great for kids. For adventurers, Makapu’u Beach Park offers paragliding lessons.

Eat & drink:

Lunch - Nico’s Pier 38 for seafood, Kaka’ako Kitchen for gourmet plate lunch, Helena’s Hawaiian Food for haupia, lomi lomi salmon, poke, and kalua pork, Wailoa Shave Ice for shave ice ((my favorite flavor is rainbow with mochi balls, ice cream, and condensed milk) and spam musubi, breakfast at Koko Head Cafe. Leonard’s for malasadas or portuguese donuts.Yakiniku Hiroshi (Japanese BBQ). Aracino (Italian). Addiction, the nightclub located at The Modern Honolulu (smart casual dress code).


Get on a 30-minute interisland flight on Hawaiian Airlines to the Big Island, either to the Kona-Kailua Airport or the Hilo Airport. Expect to pay around $100 one way.

Find more info: Oahu on Wikivoyage


Big Island

3 nights


Big Island is raw with beauty. It is the youngest and biggest of the Hawaiian islands and has a dry, sunny Kona-side and a wet, lush Hilo-side, so it’s best to book separate accommodations on either side to avoid a long, tiring drive back. It is only island where you can catch the flow of red hot lava from a hot spot right beneath the island and the only place in Hawaii where it snows. Excellent for star gazing, snorkeling and eating.

What to do:

Day 1: Arrive at Hilo Airport and pick up rental car (four-wheel drive best). You can to see active volcanoes by air, water or on foot. If you are pressed for time and can spare the cash, do a one-hour helicopter ride (expect to pay about $200 per person). Book in advance for the tour. On a normal day, you will see smoke, some molten lava slowly snaking its way down the volcano, and older lava flows that spared a few houses while it swallowed the rest of the town, as well as waterfalls and acres and acres of macadamia tree farms. If you get lucky, you may see more active lava action and clouds of steam as boiling lava rushes into the cool blue ocean.

After the helicopter ride, drive north along Highway 19 to Hilo Farmer's Market in the morning for local crafts and food. Continue the drive to Akaka Falls, a half-mile loop footpath leading up to a 400+-foot scenic waterfall. On the way back to the main highway, stop by the tropical fruit stand and pick up some ripe mangoes and papayas. For the more adventurous-type, you can call ahead to book a half-day zipline tour over the many waterfalls in this area.

Drive south to Hawaii Volcanoes National Park to learn about volcanoes and Hawaii’s geology. Check out the onsite museum and then walk inside the barren volcano crater and dark lava tubes, smell the steam from sulfur banks, and explore the fern forests that have colonized hardened lava left from previous eruptions. If you are lucky, you may see a red glow, especially at dusk, from the crater. Amazing photo ops here. Stay overnight in Hilo or one of towns near Hawaii Volcanoes National Park.

Day 2: Because the drive from Hilo to Kona takes 3 hours, hit the road early and do a pit stop at Punalu'u Black Sand Beach on route and get up close and personal with sea turtles sunbathing on the black sand beach. DO NOT touch them as that is illegal. Drive around the southern tip of the Big Island, the southernmost point in the U.S., and stop by Pu'uhonua o Honaunau National Historical Park where the site of an ancient Hawaiian heiau, or temple, offered refuge, and essentially asylum, to those condemned in ancient Hawaii. It’s also next to the much-beloved local snorkeling haven called the “Two-Step”, where the tiered lava shelf is one of the most incredible snorkeling spots on the planet. Because much of the hardened lava has not had time to erode into sand, the “Two-Step” has some of the clearest waters for snorkeling in the world. Arrive before noon for calm water and to avoid crowds. DO NOT go in if the currents are too turbulent and cloudy. Drive further north and stop by one of the Kona coffee plantations for a local tour and tasting. Pick up a bag of Kona coffee.

Day 3: Drive north on Highway 190 to check out rural pastures and Big Island farms in Waimea. Stop by Parker Ranch for a historical tour of the local paniolo, or cowboy, culture. Drive further to Kapaau, the northern most point on the island and the birthplace of King Kamehameha I, where the first bronze statue of the king, which was previously lost at the sea, now stands. Arrive at Pololu Valley Lookout and hike around there for some stunning views of the majestic North Kohala district. On the drive back, visit cute souvenir shops and cafes that line the streets along Highway 250 and enjoy a delicious, locally-sourced, all-natural, grass-fed black Angus beef burger at Village Burger in Waimea. Drive up Mauka Kea before sunset and stargaze 14,000 feet above sea level at the Mauna Kea Observatory (the only place on Hawaii that snows!). Make sure you have a full tank of gas and four-wheel drive, especially during the winter months. Drive back to Kona to enjoy poke, or Hawaiian sashimi, and wash it all down with a pint of Kona Longboard at the Kona Brewing Company.

Eat & drink:

Village Burger for amazing grass-fed burgers, Kona Brewing Company for beer tasting, Manago Restaurant for the best and biggest pork chop ever, Da Poke Shack or Umeke’s for poke, Honu’s Beachside Restaurant for casual fine dining.

Where to sleep:

We stayed at Bebo’s Bunkhouse-Kona Coffee Farm for a rustic, warm farm experience with Bebo’s dog, chickens and farm fresh vegetables.

Additional tips:

Here you can try yourself to some cool activities such as night diving or snorkeling with manta rays as well deep sea fishing.

Flying in Hilo and flying out from Kona is the best way to optimize your time.


Get on a 30-minute interisland flight on Hawaiian or Mokulele Airlines to Maui ’s Kahului Airport. Expect to pay around $100 one way.

Find more info: Big Island on Wikivoyage



3 nights


Maui is known for having the most serene, beautiful beaches in Hawaii, whale-watching in the Spring, unforgettable sunset on Mt. Haleakala, and country charm in rural Hana. If you are a licensed diver, you can dive in Molokini.

What to do:

Day 1: Arrive in Kahului Airport, pick up rental car and drive 1.5 hours to Mt. Haleakala, a dormant volcano with spectacular colors and plants 10,000 feet above sea level, and watch the sunset from the summit. Notice the landscape changing from tropical to foggy tundra and finally to volcanic above the cloud layer. Drive down and stay at Kihei or Lahaina.

Day 2: Book sunrise scuba diving tour at Molokini, a small islet off that boasts turtles, manta rays and reef sharks and other residents. From December to March, you may also encounter whales on the boat ride to Molokini or hear their songs as you are diving. Spend the rest of the day beach hopping along the Wailea coast where it has some of the most serene, beautiful beaches on Maui, including the popular Makena Beach. Or rent a surfboard or a SUP (stand up paddleboard) and learn how to surf or paddleboard (it’s harder than it looks!).

Day 3: Drive along the titillating curves on the Road to Hana, and enjoy photo ops at every turn! Watch sunset cliff diving at Kaanapali Beach. It’s only 15 minutes, so don’t be late! Drive back to Lahaina for the tropical night life.


Take the first morning ferry to Lanai for a day trip. Book in advance for tickets. Expect to pay $30 per person roundtrip.

Find more info: Maui on Wikivoyage



0 nights


Lanai is famous for its pineapples and, most recently, as the an island privately purchased by Larry Ellison, the founder and CEO of Oracle. That said, it is open to public visitors. Come for a swim in the tidepools with dolphins at Hulopoe Beach, world class golf, horseback riding or a sight of Sweetheart Rock or petroglyphs at Shipwreck beach, and Martian landscape at the Garden of the Gods.

What to do:

Enjoy the beautiful sunrise ferry on route to Lanai. Arrive at the dock and take a 30-minute bus to Lanai City to pick up rental car (only jeeps or four wheel drive allowed on the island). Examine petroglyphs and enjoy pristine beaches at Shipwreck Beach where you can still see the tanker shipwrecked on a reef. Check out the Four Seasons in Lanai City and play a round of croquet on its grounds or enjoy the dozens of orchids in its white conservatory. Those staying overnight and not pressed for time can take a horseback ride on the many ranches in Lanai City. Drive to see barren, red Martian landscape at the the Garden of the God. Return rental car in Lanai City and take the shuttle bus down to sea level for a enjoyable lunch at the Four Seasons in Manele Bay (remember to order some Lanai pineapple). Take a dip in the tidepools with dolphins in Hulopoe Beach, and if time permits, hike to Sweetheart Rock.

Eat & drink:

It’s worth stopping by the Four Seasons in Manele Bay for a drink on the terrasse with a splendid view.


Take ferry back to Lahaina and drive one hour to Kahului Airport and take a one-hour plane ride to Kauai’s Lihue Airport. Expect to pay $100 one-way. Alternatively, fly out directly from Lahai Airport and transfer to Kauai’s Lihue Airport from Honolulu.

Find more info: Lanai on Wikivoyage


That’s it for a packed 14-day itinerary! You can fly back home from Honolulu. With more time, you can tack on several more days on the island of Molokai for some beach time, hiking and horseback riding!