A First Timer’s Guide to Hawaii Holidays 

Hawaii—nicknamed The Aloha State, a fitting name for these welcoming islands—is home to volcanic landscapes, the highest sea cliffs on earth, otherworldly sunsets, historic landmarks like WW2 Pearl Harbour memorials, and of course, Moana. Comprising four major tourist islands including Hawaii (Big Island), Oahu, Kauai, and Maui, the USA’s 50th state presents a beautiful holiday destination for couples, families, and groups. 

If you’re a first-timer, all these options might leave you wondering where to begin. Yet each island presents its own unique experiences, scenery, and culture, and we’re here to help you plan a bespoke Hawaii holiday. 

(Mahalo us later). 
 

Hawaii (Big Island) 

Great for… nature  

The Big Island is twice the size of all the other Hawaiian Islands combined yet feels unexpectedly quiet in comparison to its busier sisters. With varied landscapes encompassing several climate zones, you can explore colossal volcanic elevations, lush inland valleys, and captivating black-sand beaches. 



You don’t need to be a geologist to be mesmerised by the striking volcanic landscapes of The Big Island. Its primary attraction, Hawaii Volcanoes National Park, is a must-visit for anyone making a trip here and is the home to one of the world’s most active volcanoes, Kīlauea, as well as the world’s largest, Mauna Loa. With diverse terrain throughout its 523 square miles, you can hike challenging trails and rugged lava fields, explore tropical rainforests, and drive round the crater rim or Chain of Craters Road to witness the dramatic landscape up close. 

The Kona District on the island’s western coast is the main tourist hub and features everything from chilled out coffee farms and picturesque beaches to a rich culture, found in Puʻuhonua o Hōnaunau National Historical Park. 
 

Maui 

Great for… activities and family fun 

Maui is considered a good all-rounder destination for its classic island holiday vibes, embodying the best of both worlds: urban and nature. Luxury resort hotels, impeccable sand beaches in all colours, and world-class experiences and activities make this island a great base for families and thrill-seekers alike. 



On land, Maui offers adventure at every turn. Take to riding horseback across its rolling hills, tee off on its pristine golf courses, zipline through leafy canopies or rappel down a cooling waterfall to get the most out of this marvellous place. And in the water, you’re all set for snorkelling, kayaking, or swimming on its glorious beaches—check out the picture-perfect Kapalua Beach or Makena Beach for golden sands and crystal-blue waters. Maui is also one of the best places in the world for whale-watching; your best time to witness these humpback giants is between November and April. 
 

Laid-back seclusion – Kauai 

The ‘Garden Isle’ feels a world away from the hubbub of the tourist hotspots in Oahu and Maui, with lush jungles, underground canyons, and scenery so astonishingly beautiful it needs to be seen to be believed. Over half of the island is a conservation area, so there are plenty of opportunities for peaceful birdwatching, paddleboarding, and hiking in near-isolation.  



The breathtaking, serrated cliffs of the Nā Pali Coast are perhaps most well-known for the helicopter scene in the original Jurassic Park, and you can even book your own chopper excursion to get that full-on movie experience!  
 

Urban fun and famous beaches – Oahu 

With Honolulu—the state capital—and the famous resort of Waikīkī to its name, Oahu packs a punch and is home to most of the state’s diverse population. If you’re seeking a mix of gleaming skyscrapers, iconic beaches, and historical landmarks, this may be the destination for you. Your Hawaiian dream will likely begin here as most international flights touch down in Honolulu, which presents a great spot for city living – think rooftop pools, pumping bars and restaurants, and world-class shopping. 



History buffs will also love exploring Pearl Harbor, and there are plenty of cultural landmarks and museums to visit including the National Cemetery of the Pacific, Honolulu Museum of Art, ‘Iolani Palace, and The Bishop Museum for a glimpse into Hawaii’s native culture and rich history. 



If chilling out and gentle surfing are your main goals, stick to the golden sands of Waikīkī Beach and enjoy the plethora of luxury resorts, excellent restaurants, and lively entertainment options along its shores. 
 

How many days are needed in Hawaii 

Distance alone rules Hawaii out from being a weekend break, as flight times from the UK are around 17 hours with one stop in-between. If you plan to stay in one place, then a week should be enough time to explore, relax, and get a feel for the island.  

However, if island-hopping is on your agenda, 10 days or two weeks will be ideal. There are no ferries between islands, but frequent flights lasting about 30-45 minutes mean that getting around Hawaii is a breeze.  
 

Hawaii multi-centre ideas 

Sitting in the Pacific Ocean, the islands of Hawaii make for a great beach destination if you’re planning on travelling to the USA’s West Coast. Pair Hawaii with a fun city break in Los Angeles or San Francisco or combine an exciting Disneyland trip in Anaheim, California with a relaxing stint on Waikīkī Beach to unwind and shake off those theme park thrills. 



There are several cruise lines operating in Hawaii too, meaning you can island hop without the fuss of packing and repacking to go to the airport! 
 

What to pack 

There’s no bad time of year to visit Hawaii and you’ll be comfortable in shorts and t-shirts year-round. But Hawaii is also home to 10 of the world’s 14 climates, so a bikini one day may need replacing with a sturdy raincoat the next, depending on where you visit!  

If you plan on hiking and swimming then you’ll need a good pair of walking shoes or boots, appropriate swimwear, hats, sunglasses, insect repellent, and waterproof jackets for those drizzly rainforests.  
 

Planning tips 

Consider renting a car 

Renting a car in Hawaii is a great way to make the most of your trip and explore beyond the main tourist areas. If you're staying in Waikiki on Oahu, you might find that you don’t need a car every day as there’s plenty to do within its compact two-mile strip.  

To save money on pricey hotel parking fees, consider renting a car only on the days you plan to venture out and explore the island. On the other, less populated islands, a car is a must for exploration! 
 

Travel during the shoulder season 

Hawaii is a year-round destination, so the weather shouldn’t make too much of an impact on your preferred travel dates. However, there are still busier seasons and quieter ‘shoulder’ seasons (April/May and September/October) with fewer crowds and cheaper costs, which may influence your decision.  


 

Make a list of experiences you want to do 

With so much to do on all the islands, you’ll struggle to get everything done even if you were here for a whole month, so it’s always a good idea to jot down and plan your must-do activities so you can maximise your time in Hawaii.