On the whole, Hawaiʻi is pictured as a tropical paradise, characterised by golden beaches, swaying palm trees and azure waters, and while you’ll certainly find plenty of that, Hawaiʻi offers so much beyond the postcard-perfect views. Made up of eight main islands, the 50th U.S. state is fascinating. View the incredible scenery, much of which you’ll recognise from your favourite Hollywood blockbusters, but also immerse yourself in a culture shaped by centuries of Polynesian heritage and a deep connection to the land and sea.
Here is our guide to four of Hawaiʻi’s most popular islands, and how to spend your next two week vacation exploring. Let us help you make the most of your Hawaiʻi holiday.
Oʻahu is home to the famous city Honolulu and the beach of Waikīkī. It is also where you can discover peaceful retreats along the unspoilt North Shore, explore breathtaking beaches, poignant historical sites, and a buzzing food scene. Whether you’d like to try your hand at surfing, learn about Hawaiʻi’s history, hike to magnificent viewpoints, or immerse yourself in Hawaiian traditions, Oʻahu has so much to offer…
Honolulu is a buzzing city, awash with dazzling colours. The city is surrounded by vivid blue waters and golden beaches, contrasted by the bright lights on the city skyscrapers and a backdrop of lush greenery.
When you touchdown in this island paradise, collect your car from the airport and check in to your hotel, before venturing out to explore the city. The perfect introduction to these incredible islands is immersing yourself in the history of Hawaiʻi. Get an insight into the Hawaiian monarchy, by exploring the ornate architecture and fascinating history of the ʻIolani Palace, the only royal palace in the US. The Bishop Museum showcases history and science exhibitions, offering an insight into Hawaiʻi’s fascinating culture, as well as the islands’ geology and ecosystems.
Head down to Kāhala Beach in the evening and treat yourself to a Mai Tai as you watch the glorious sunset over the ocean.
Our recommended Honolulu hotel: Outrigger Reef Waikīkī Beach Resort
One of the most famous beaches in the world, Waikīkī is the perfect place to learn to surf, or spend an afternoon relaxing on the soft sands. Waikīkī’s buzzing beach resorts are framed by modern skyscrapers and luxurious hotels, but there’s an inimitable laid-back vibe that permeates the warm air here.
After wandering the beach, overlooked by towering Lē’ahi (Diamond Head Crater), you can reverse your vantage point, by hiking up to the crater. At 760 feet high, it offers spectacular views over Waikīkī and Honolulu, in return for a challenging hike. Over time, it has had various uses, including an ancient place of worship and a military fort, so you can gain an insight into Hawaiʻi’s past, as well as taking in the views.
If you’d rather a less intense walk, the Waikīkī Historical Trail provides a fascinating insight into the history of the area, as well as an opportunity to stretch your legs and take in the views. Along the route, surfboards plastered with information take visitors on a journey back in time – the perfect way to spend a few hours.
In the evening, head towards Kalākaua Avenue, lined with shops, bars and restaurants. Experience Hawaiʻi’s famous hospitality, and get involved in a traditional lū’au celebration. The perfect place to immerse yourself in Hawaiian traditions is Kūhiō Beach, that hosts the weekly ‘Kūhiō Beach Hula Show’. This free performance is the perfect way to experience authentic Hawaiian music and traditional Hālau Hula performers as the sun sets over the beach.
The next day, explore one of the most historical sites in the US: Pearl Harbor. Deriving its name from the pearl oysters that were originally harvested there, on December 7th 1941, it was the site of an unexpected air assault by Japanese pilots and saw the USA enter World War II. Learn about the tragedy through five informative but sobering historical sites, and listen to tales from survivors, see photographs showing the destruction and remember those who were lost at the memorial statues.
That afternoon, travel 30 minutes further east to Kualoa, a spectacular nature reserve. It is no surprise that this striking scenery has featured in numerous Hollywood films, starring in Jumanji, Godzilla and Jurassic Park. Explore the reserve by e-bike or catamaran, hike around the reserve, travel by 4×4 or even on horseback.
After exploring the south of the island, head to Oʻahu’s laid-back North Shore. A high-profile surf spot, North Shore hosts some of the world’s most prestigious surfing competitions, including the ‘Vans Triple Crown of Surfing’. The waves are best suited to confident surfers during the winter months, whilst in spring and summer, the waters are more tranquil and ideally suited to swimming or beginner surfers.
Haleʻiwa is a historic surf town and the cultural hub of the North Shore, with a buzzing food scene, charming art galleries and boutique shops. One of the best ways to experience Hawaiʻi’s delicious food offerings is by checking out the area’s famous food trucks. It’s the perfect way to support local businesses, and sample a few different Hawaiian dishes. The must-try dishes in Hawaiʻi include famous poke, a seafood salad, often featuring marinated tuna. Kālua pig is also delicious, slow-cooked and seasoned with salt before smoking. If you’re in need of some hearty, comfort food, why not try Loco Moco, comprised of a hamburger, rice, gravy and a fried egg.
Known as the “Garden Island”, Kauaʻi is draped in emerald valleys and gushing waterfalls, and punctuated by sharp mountains and jagged cliffs. A filming location for Jurassic Park, King Kong and Pirates of the Caribbean, amongst others, Kauaʻi’s stunning landscapes are unrivalled. This makes for incredible hiking and outdoor activities.
Kauaʻi is the next stop on your Hawaiʻi island-hopping holiday. You will fly into Līhuʻe, the second largest town on the island, where you can pick up your car. In Līhuʻe, buy up some poke and explore the Kauaʻi museum, before heading to Poʻipū Beach. Famous for its snorkelling, fishing, surfing and bodyboarding, get stuck into some water sports, or simply soak up the sun from the beach and watch the action.
Spending the afternoon at Poʻipū Beach, there is a good chance you will able to spot the resident Hawaiian monk seals sunbathing on the shores. One of only two mammals endemic to the Hawaiian islands, monk seals are endangered, so it is important to keep your distance if you are lucky enough to spot one, staying at least 150 feet away!
If you’re seeking adventure, Kauaʻi’s reputation as the “Garden Island” lends itself perfectly to outdoor activities. Soar through Kauaʻi’s lush mountainous backcountry on a zipline tour, or float through the magnificent scenery on a tubing adventure!
Our recommended Kauaʻi hotel: Koloa Landing Resort at Poʻipū
Continue to explore the island’s incredible scenery throughout next day. Just north of Līhuʻe, you’ll find Wailua River State Park. At the southern end of the river, it begins to meander forming two streams that cast a spectacular double waterfall. Wailua Falls hold deep significance in Hawaiian history, as, according to legend, Hawaiian warriors once proved their bravery by leaping from the top of the falls into the swirling waters below. Wailua Falls are easily accessible by road, so take a moment to admire the sheer power of this natural wonder before continuing your journey to the Kalalau Trail.
The Kalalau Trail is an 11 mile network of challenging trails, offering spectacular views of cascading waterfalls, lush greenery and the jagged coastline. Whilst hiking the entire trail involves a multi-day backpacking adventure, a popular day hike takes you from Keʻe Beach to Hanakāpīʻai Beach. On a 4 mile round trip you can explore the Nā Pali coastline and enjoy beautiful ocean views. Just make sure to make a reservation for the Hāʻena State Park before you go!
Known as the ‘Grand Canyon of the Pacific’, the canyon was carved by the Waimea River, thousands of years ago. Stretching a whopping 14 miles in length, 1 mile in width and 3,600 feet in depth, this geological wonder is unlike anything else you’ll find on the Hawaiian Islands. The layers of rock offer a fascinating insight into the island’s volcanic history.
Take in the views of miles of rugged crags and deep valley gorges, the orange hues of the rock offering a striking contrast to the lush greenery scattered over the rockface. If you’re feeling adventurous, you can hike up the canyon, with trails suitable for beginners and seasoned hikers alike, but if you’d simply like to enjoy the views, there are several lookouts accessible by car.
The largest in the archipelago, the Island of Hawaiʻi boasts incredibly diverse geography and lends itself to a holiday filled with unique experiences. Scattered with volcanic peaks, lush green forests and sweeping bays, this is a holiday backdrop that is reminiscent of a coffee table book or a movie scene.
After flying into Kona Airport, head to Kailua Village (Kailua-Kona), just 15 minutes south. Once a sleepy fishing village, then a retreat for Hawaiian royalty, Kailua-Kona is now a lively seaside town. Take a stroll down Aliʻi Drive offering some of the island’s best shopping, great restaurants, and several historic spots. You’ll find Mokuʻaikaua Church, dating back to 1820 when the first Christian missionaries arrived, and Huliheʻe Palace, previously a holiday home for Hawaiian royalty.
After exploring Kailua Kona, head to the beaches of North Kona and the Gold Coast of South Kohala. These shores are stunning, with a striking blend of black lava rock and glistening white sands. The beaches are a snorkeller’s paradise, and there’s a great chance you’ll spot turtles and manta rays! It is also the perfect place to watch the sunset.
The next day, head to Kona, a region famous for its coffee. No trip to the Island of Hawaiʻi would be complete without sampling some of its specialty brews, so we’d suggest you take a tour of one of the region’s coffee farms. Regarded as some of the best in the world, Kona blends tend to have a distinctive smooth and slightly nutty flavour. Explore the 5.5 acres of Kona Coffee Living History Farm, where you’ll have a front row seat to the working farm’s agricultural processes and coffee production.
To sample some more local delicacies, head to Kona Farmers’ Market, with an array of offerings all produced or crafted on the Island of Hawaiʻi. Thanks to the area’s climate, Kona’s soil is said to be some of the richest soil in the world. This means you’ll find delicious, fresh fruits and vegetables, and beautiful, bright flowers. Spend the afternoon wandering through the stalls, chatting to the vendors and artisans, and maybe treat yourself to a unique souvenir.
Our recommended Kona hotel: Royal Kona Resort.
Maunakea is a dormant volcano, and is the highest point in all of the Hawaiian Islands. Named by early Hawaiians as “white mountain” due to its snow-capped peaks, it is breathtaking from the ground, and, naturally, boasts spectacular views from the top.
Hawaiʻi is famed for its dark, clear night skies, making it a perfect place to marvel at the stars. One of the best locations to stargaze is the summit of Maunakea. You can reach the top by hiking independently, or take a guided tour to learn about the region and the constellations to really make the most of your trip.
Another fantastic reason to take a tour here is that Maunakea is a sacred place for Hawaiians. It is where Poliʻahu, the snow goddess, resides and hiking with a knowledgeable guide is the perfect way to gain an insight into the culture and mythology of the archipelago. For the best views, aim to arrive half an hour before sunset to enjoy mesmerising views of the islands before the stars start twinkling.
An active volcano, Kīlauea Volcano is one of the most popular sights on the island. Standing more than 1,200 metres tall, this iconic mass emerged over 100,000 years ago and is a focal point of the Southern Shore and the Hawaiʻi Volcanoes National Park. Spanning over 1,300 square kilometres, the park is a magnificent geographical wonderland, with lava fields speared by conical cauldrons and giant craters.
Guided hikes, helicopter tours and even ocean excursions offering sensational views from the ocean are popular ways to take in the sights and wonders of the island’s volcanoes. Tours, meanwhile, provide incredible views of molten lava and an appreciation of the scale and dominance of the park’s main attractions.
Visit Hawaiʻi Volcanoes National Park as part of our Hawaiian Discovery Tour.
Spend the final three days of your Hawaiʻi holiday on the paradise island of Maui. Arguably, the best-known of the islands, Maui has certainly earned its reputation. Maui boasts Hawaiʻi’s signature golden beaches and swaying palm trees, as well as towering mountains and rich farmlands. You can fill three days without any problems, but we’d recommend you experience these highlights.
Fly into Kahului Airport, before heading to Kāʻanapali Beach, just less than an hour away. Once earning the title of America’s best beach, Kāʻanapali Beach boasts a three mile stretch of pristine white sands.
Kāʻanapali Beach is the gateway to some of Hawaiʻi’s best whale watching. After spending the summer in Alaskan waters, Humpback Whales make the incredible 3,500 mile journey down to the warm waters of Maui every autumn, sheltering in the Auʻau Channel to mate and give birth. They rest here for the winter, before migrating back by the end of April. Although whales can be spotted from all of the Hawaiian Islands, the Auʻau Channel offers one of the best whale-watching spots in the world.
Whales are particularly culturally significant for Native Hawaiians, as they play a considerable role in Hawaiian legend, and the return of Humpback Whales is viewed as a homecoming. Take a whale-watching tour to witness these incredible creatures up close for yourself.
Returning to Kāʻanapali Beach for the evening, you can watch the daily cliff diving ceremony. At sunset, a cliff diver dressed in traditional attire will light torches along the cliff, offer his lei to his ancestors, before diving into the water below, a fearless re-enactment of a feat performed by Maui’s revered King Kahekili.
Our recommended Kāʻanapali Beach hotel: Outrigger Kāʻanapali Beach
The following day, make your way to Kula, in Upcountry Maui. The rich volcanic soil of Haleakalā means the region is known for its farming and delicious fresh produce. The perfect way to start your day is with a farm-to-table breakfast. A feast of knowledge and delicious food, learn about sustainable farming whilst you enjoy a meal crafted with fresh, local ingredients.
The best way to experience Kula is by taking a farm tour, with a huge variety experiences on offer. One of the most unique tours is a visit to the Ali’i Lavender Farm, perched on the slopes of the Haleakalā Mountain. Wander through the fragrant gardens, take in the soft pastels of the lavender fields and enjoy a refreshment with panoramic views over Maui.
Perhaps indulge in some of the island’s signature wellness practices in the afternoon, heading to a spa for a Lomi Lomi massage. This ancient Hawaiian healing art consists of rhythmic movements and long forearm strokes that aim to sooth, realign the body and improve circulation. Alternatively, a traditional sound healing session offers a meditative experience. Using the sounds of crystal singing bowls and gongs, the practise promotes relaxation and stress reduction.
Scaling the dizzy heights of Haleakalā is undeniably the best way to see the awe-inspiring natural beauty of the island of Maui, making it the perfect ending to your Hawaiʻi holiday. Dotted around the giant rim of the gaping mouth of the volcano, lookouts provide spectacular views of volcanoes, lava fields and the golden beaches in the distance.
Hiking here is a special experience and it’s also possible to cover the rugged terrain on two wheels. For those keen to enjoy everything the park has to offer and profit from an authentic under-the-stars experience, camping is also available with a permit. Be sure to take a look in the visitor centre, which has all the information needed to plan a hike or find the best viewpoints.
When it comes to exploring on foot, the Pīpīwai Trail is a popular choice. The meandering trail takes around two hours in total to complete and brings visitors through bamboo groves and river banks along the Palikea Stream. The cascading torrents of Makahiku and Waimoku Falls make for spectacular sights along the way.
Whether you have two weeks or more to explore, or just a few days for an island getaway, a Hawaiʻi holiday is the perfect way to experience a little slice of paradise and learn about a fascinating culture. You can embark on an Hawaiʻi island-hopping holiday, or learn from the experts on an escorted Hawaiʻi Four Island Adventure.
If you’d like to build a unique itinerary from scratch, get in touch with our America Experts, who would be delighted to plan you a personalised itinerary.
Holidays to Hawaiʻi by Freedom Destinations
Grace is part of the Marketing Team at Freedom Destinations, having recently returned from 3 months backpacking around Australia. Her travels have also taken her to Canada, the U.S. and Thailand so far, but her travel wish list is far from complete!
