Hawaii Trip: The Ultimate Vacation Guide
Hawaii’s pristine beaches and picture-perfect panoramas have likely already earned it a place on your bucket list of dream holiday destinations.
Hawaii is a volcanic archipelago consisting of six main islands in the Pacific Ocean, and the 50th US state. Its lush rainforests and idyllic surf towns have served as the backdrop for TV phenomenon Lost, as well as big screen hits such as Jurassic Park and Indiana Jones: Raiders of the Lost Ark.
There is so much to see and do across all the islands that forming an itinerary for a Hawaii trip there often proves to be a struggle.
Luckily, we’ve done the hard work for you, and created the ultimate two-week itinerary for a Hawaiian holiday, covering Oahu, the lesser-known Molokai, Maui, and Hawai’i, commonly known as ‘The Big Island’.
We suggest flying into Oahu’s Honolulu Airport (HNL). As Hawaii’s largest airport, it’s very likely that flying into HNL will be the simplest and most direct route to start your Hawaii trip.
Skyscanner.com is your best bet for bagging a good deal – especially if you’re browsing incognito. Use it to compare airline prices, and plan your flight.
We also highly recommend renting a car on each island – especially Maui and Hawai’i – but if this is a little out of your budget, then there are other ways to get around too.
You’ll be spending a total of four nights on the island of Oahu, so once you arrive, settle in and relax in preparation for starting your first full day in Hawaii!
Day One: Aloha, Hawaii!
It’s your first day in Oahu!
Wake up in Honolulu and travel back in time with a tour of Pearl Harbor, including the USS Arizona, and on-site museums and galleries.
This visit concludes with a driving tour of Honolulu, where you’ll see historic attractions such as ‘Iolani Palace, Washington Place, and the state capital building.
In the afternoon, take a stroll through the trendy Waikiki neighborhood, where you can find some great dinner spots down by the beach.
Day Two: Tour the North Shore
Choose a Full-day tour package. You will be sure to catch all of the highlight of the island's north shore!
There are several options to be picked up in Waikiki, and begin your day of spectacular scenery in the Ko’olau Mountains, where you’ll visit the Valley of Temples.
The best options include a visit to a traditional shrimp farm, the beautiful Waimea Canyon, rare green turtles at Turtle Beach, and the small surf town of Haleiwa, before tucking into a delicious lunch at a North Shore Shrimp Shack.
Day Three: The Flavors of Hawaii
Enjoy a lazy morning on one of Oahu’s many beaches: the clear, calm waters of Lanikai beach make it our favorite.
Later in the day, take an authentic, 3-hour cooking class, where you’ll learn how to make classic Hawaiian dishes such as poke, and coconut shrimp, as well as local snacks and desserts.
You’ll enjoy your freshly made dishes at the end of the class, before leaving with full bellies and new recipes to take home with you!
Day Four: Last Day on Oahu
Spend your final morning in Oahu hiking up the Diamond Head Summit Trail.
Diamond Head (or Le’ahi, as it is locally known), is an extinct volcano offering astounding views over Oahu, the ocean, and the huge volcanic crater that lies just beneath it. A must in your Hawaii trip.
You won’t break too much of a sweat – it takes less than an hour to reach the top!
In the afternoon or evening, grab a 30-minute flight to the friendly isle, Molokai, where you’ll be spending the next three nights.
Day Five: ‘The Friendly Isle’, Molokai
Molokai is far quieter and less busy than the other Hawaiian Islands, making it the perfect place to take some time to yourselves.
Head to Dixie Maru beach, where you can kick back and unwind. Be sure to pack your own food and drink, and plenty of sunscreen, because this sheltered cove makes for a private paradise – although you may find yourself in the company of some happy, sunbathing monk seals!
If you fancy exploring deeper into the island, head north to the quirky Hoolehua post office, where you can post a hand painted Molokai coconut – send it to a loved one in place of a traditional postcard, or have it delivered back home as a holiday keepsake that you’ll cherish forever.
Day Six: Exploring Kalaupapa
At the northern tip of the island lies the remote Kalaupapa National Park.
When Hansen’s disease – or leprosy, as it was known then – arrived on the island in the 19th century, Kalaupapa was used as an isolation settlement for those affected. Today, the disease is curable, but some descendants of the original colonies still live in this secluded peninsula.
It is difficult to access Kalaupapa, but you can do so by taking a cliff-edge mule ride into the park, offering breathtaking views along the way.
You’ll spend the day exploring the park and the existing settlement, and enjoying a picnic lunch looking over the devastating beauty of the Kalawao coastline.
Be sure to secure a place on this tour well in advance, as spots get booked up fast!
Return from your tour to enjoy your third and final night in Molokai!
Day Seven: Voyage to ‘The Valley Isle’
Take a flight from Molokai to Maui, where you’ll get settled in your accommodation and take some time to relax.
We really advise renting a car in Maui due to the freedom it will give you in exploring the island.
Start by taking an afternoon helicopter ride around the island for a truly unforgettable experience. We recommend to check the routes offered by Blue Hawaiian Helicopter Tours. Don’t forget your camera for this one, the best snaps on your Hawaii trip - sweeping panoramas of rugged coastlines, cascading waterfalls, misty rainforest peaks, vast valleys, and the Haleakala Crater.
Day Eight: Maui's Natural Beauty
Today’s itinerary is especially perfect for a romantic retreat, although it can still be enjoyed by everyone!
Early in the morning, head out to the Nakalele Blowhole, a natural geyser on the northwestern coast of Maui. If you take the trail in from the 38.5-mile marker out of Kapalua, you’ll catch sight of Maui’s famous heart-shaped rock, a perfect opportunity for a sentimental photograph!
Watch the geyser in action as it ejects a pillar of water 100 feet in the air. You’ll see rainbows shimmering in the mist around the blowhole on your morning visit, and if you’re lucky you’ll be able to spot some whales in the ocean behind it! Just remember not to get too close, and stay on the dry rocks!
Spend the afternoon in the quaint town of Lahaina – don’t miss the shops on Front Street, or the fascinating Banyan court to see the oldest living tree on Maui.
End your day with a romantic dinner date at the incredible Lahaina Grill, where you can treat yourself to their tasty beef filet, or their mouthwatering vegetarian option, Portobello mushroom ravioli.
Day Nine: The Road to Hana
This mini road trip across Maui from Kahului to Hana is one of the most scenic drives in the world, so it makes sense to devote a whole day to it.
Make your first stop at the hippy surf town of Paia, where you can grab an awesome breakfast or brunch at the Paia Inn Café.
You can see all the best stops on the Road to Hana on the official website, but some of our highlights include the short, picturesque hike to Twin Falls, the freshly baked banana bread at the ‘Halfway to Hana’ stand, and of course, the charming Hana Town itself.
The entire route is jam-packed with incredibly photogenic views of the ocean, rolling hills, and vivid bamboo forests – not to be missed!
Day Ten: A Day at Molokini
Today is an early morning start in your Hawaii trip, but you’ll thank us for it.
Book the Mololo Catamaran from Maalaea Harbor for a visit to Molokini, a crescent-shaped, partially submerged volcanic crater off the Maui coast.
To start off, savor your continental breakfast on board the boat, and stop for an hour of snorkeling within the vibrant marine life around the crater.
Once back on board you will be treated to a tour of Molokini’s wildlife, most notably the abundance of seabirds that live there. You’ll then enjoy a deli lunch as you sail from Molokini to Turtle Town, where you’ll stop for more snorkeling, this time in the midst of Hawaii’s rare green turtles.
Once you arrive back at the harbor in the early afternoon – you will probably want to take the rest of the day to relax after your busy morning, either on the beach or just lounging at your room.
Day Eleven: Kula and Goat Yoga
You’ll commence your day with a picturesque drive ‘up-country’ through the stunning Kula district, where you’ll take some time for yourself with a unique yoga class on the hilltop, surrounded by miniature goats!
Refuel with lunch on the garden terrace at Kula Lodge, where you can dine on wood-oven pizza with a spectacular view.
Later in the afternoon or evening, travel to ‘The Big Island’ for the last leg in your Hawaiian journey.
Day Twelve: ‘The Big Island’
On your first day in Hawaii, head to the sunny Kona coast and spend your day on one of the many beaches there, or ambling around the old Kailua-Kona village.
Later on, take part in night snorkeling while huge Manta Rays swim beneath you!
Day Thirteen: Hilo and Hot Springs
Today, you’ll experience the many delights of the town of Hilo, and its surrounding area with an exciting tour!
Your tour begins with a trip to the gorgeous Akaka Falls, and leads on to the Hilo farmers market, the Nani Mau botanical gardens, and the Lava Trees state park.
The tour culminates with a visit to Kapoho, where you can take a refreshing dip in the warm tide pools.
Celebrate your final evening in Hawaii with dinner and cocktails right on the sand at the Beach Tree restaurant.
Day Fourteen: Final Day
It’s the final day of this amazing Hawaii trip!
Spend your last morning at the Volcanoes National Park, where you can hike the Sulphur Bank trail, and trek around the Kilauea’iki crater.
After this, fit in a few last hours of sunbathing on the remarkable black sands of Punalu’u Beach (any trip to Hawaii absolutely requires a visit to a black sands beach!), before heading back to your accommodation and preparing to leave the island.
Take a short domestic flight back to Oahu, where you’ll be able to catch your flight home!
So, there we have it!
Our ultimate 2-week itinerary, packed with adventure, relaxation, and glorious views!
We understand that all the activities we’ve mentioned may not be for everyone, but one of the many great things about Hawaii is that there’s just so much to see and do – if there’s something that doesn’t take your fancy, you can easily swap it for something else that does!
You can also easily lengthen your Hawaii trip to include another island, or simply spend more time in each place. And of course you can cut out an island to shorten your trip!
While you may not want to follow every last detail of this plan, it serves as a great base when planning the trip of a lifetime to Hawaii!
We hope you enjoyed our itinerary recommendations for a Hawaiian holiday – make sure you check out our
vacation rentals section to see the best places to stay in Maui and Honolulu- and keep an eye on our blog for more travel tips and itineraries!