Hawaii Holidays

At Charter Travel, we specialise in tailor-made Hawaii holidays designed around the way you want to travel. Whether you are planning a luxury honeymoon in Maui, an island-hopping adventure across Hawaii, a family holiday combining Oahu and the Big Island, or an adventurous trip to Kauai, our experienced travel specialists create bespoke itineraries with carefully selected hotels, flights and experiences. Since 1988, we have helped UK travellers discover the Hawaiian Islands with tailor-made ABTA (F8106)  and ATOL 4151 protected holidays, expert advice and personalised service from start to finish. From beachfront resorts in Waikiki to luxury escapes in Kauai, we use our destination knowledge to create unforgettable Hawaii holidays that go far beyond standard package tours.

Hawaii Holiday for 2026/2027

A Hawaii Holiday in 2026/2027 promises an unforgettable escape to paradise. Hawaii consists of four main islands, Oahu / Maui / Kauai, Big Island and the private island of Lanai - each offering unique landscapes and experiences. While you can't fly direct to Hawaii, you can fly direct to various USA cities including Los Angeles, San Francisco, or Seattle with airlines including Virgin Atlantic and connect with partner airlines such as Hawaiian Airlines and/or Delta Airlines onwards to Hawaii.

If you’re unsure which island is right for you, our team of Hawaii specialists is here to help. With expert knowledge and firsthand experience, we can recommend the best hotels and activities based on your preferences. Speak to one of our Hawaii Specialists today to start planning your Hawaii Holiday.

Plan your tailor-made Hawaii itinerary today!

Hawaii Island Hopping Holidays

One of the best ways to experience Hawaii is with an island-hopping holiday, allowing you to discover the unique character of each Hawaiian island in one unforgettable trip. Many travellers choose to combine Oahu, Maui, Kauai and the Big Island to experience everything from vibrant beaches and luxury resorts to volcanoes, waterfalls and rainforest landscapes. At Charter Travel, we create tailor-made Hawaii island hopping holidays with inter-island flights, carefully selected hotels and personalised itineraries designed around your interests. Whether you want to explore Pearl Harbor in Oahu, drive the Road to Hana in Maui or discover Hawaii Volcanoes National Park on the Big Island, our Hawaii specialists can build the perfect multi-centre itinerary from the UK.

Which Hawaiian Island Is Right For You?

Each Hawaiian island offers something completely different, which is why choosing the right combination is one of the most important parts of planning your Hawaii holiday.

Oahu

Oahu is ideal for first-time visitors thanks to its mix of iconic Waikiki beaches, nightlife, surfing and historic attractions including Pearl Harbor. Our Travel Specialists recommended hotels on Oahu include The Royal Hawaiian – A historic luxury hotel on Waikiki Beach and Hilton Hawaiian Village Waikiki Beach – A fantastic choice for families. Whilst on Oahu be sure to visit Pearl Harbor and the USS Arizona Memorial, hike Diamond Head for breathtaking views of Honolulu, experience world-class surfing on the North Shore, and enjoy shopping and nightlife in Waikiki.

Maui

Maui is perfect for luxury travellers and honeymooners looking for upscale resorts, scenic coastal drives and world-class beaches. Our Travel Specialists recommended hotels on Maui include the Four Seasons Resort Maui at Wailea – A five-star beachfront resort offering ultimate luxury and AC Hotel by Marriott Maui Wailea – A contemporary option with modern amenities. Whilst exploring Maui be sure to drive the iconic Road to Hana, watch the sunrise at Haleakalā National Park, snorkel at Molokini Crater, a protected marine sanctuary, and attend a traditional Hawaiian luau.

Kauai

Kauai, known as the “Garden Isle”, is best for nature lovers wanting dramatic landscapes, hiking trails and a more peaceful atmosphere. Our Travel Specialists recommended hotels on Kauai include the Grand Hyatt Kauai Resort & Spa – A luxurious escape featuring a golf course & world-class dining and 1 Hotel Hanalei Bay – A sustainable and wellness-focused retreat. Whilst on Kauai be sure to hike the stunning Kalalau Trail along the Nā Pali Coast, take a helicopter ride over Manawaiopuna Falls (featured in Jurassic Park), visit Waimea Canyon, the "Grand Canyon of the Pacific, and kayak the scenic Wailua River.

Big Island (Hawai'i Island)

The Big Island offers adventure, volcanoes, black sand beaches and incredible natural diversity. Our Travel Specialists recommended hotels on Big Island include the Hilton Waikoloa Village – A stunning, family-friendly resort with extensive facilities and Sheraton Keauhou Bay Resort & Spa – A peaceful retreat with breathtaking ocean views. Whilst on the Big Island of Hawaii be sure to explore Hawaii Volcanoes National Park and witness active lava flows, stargaze from Mauna Kea, the world’s tallest mountain (from base to peak), snorkel in Kealakekua Bay, where Captain Cook first landed in Hawaii, and take a tour of Kona coffee plantation and taste world-famous Hawaiian coffee.

Lanai (The Private Isle)

Lanai is a secluded and luxurious escape, perfect for those seeking tranquility and exclusivity. With its limited number of resorts, it offers an intimate Hawaiian experience. Our Travel Specialists recommended hotels on Lanai include the Four Seasons Resort Lanai – A five-star resort offering world-class dining and oceanfront views and Hotel Lanai – A charming and historic boutique hotel in the heart of Lanai City. Whilst on Lanai be sure to explore the surreal landscape of Keahiakawelo, also known as the "Garden of the Gods", relax on the pristine Hulopo‘e Beach, a marine preserve teeming with vibrant sea life, take a 4x4 adventure to Polihua Beach, one of the most secluded beaches in Hawaii, play a round of golf at Manele Golf Course, with stunning ocean views, and discover Lanai City’s unique plantation-era charm with boutique shops and cafes.

Our Hawaii travel specialists can help you decide which islands best match your travel style, budget and holiday plans. Start designing your Hawaii Holiday with a true Hawaii Holiday Expert! 

Best Time To Visit Hawaii

Hawaii is a fantastic year-round destination thanks to its warm tropical climate, making it one of the most popular long-haul holiday destinations from the UK. The best time to visit Hawaii depends on what you want from your trip. April to June and September to November are often considered ideal thanks to pleasant temperatures, lower crowds and excellent value. Winter months from December to March are popular for whale watching, surfing and winter sun holidays, while summer offers fantastic beach weather and family holiday opportunities. Whether you are planning a luxury honeymoon, island-hopping adventure or family holiday to Hawaii, our travel specialists can help you choose the perfect time to travel based on weather, budget and island experiences.

Hawaii Twin Centre Holidays

Hawaii twin centre holidays are one of the most popular ways to experience the islands, allowing you to combine contrasting destinations into one unforgettable trip. Many travellers choose to pair the vibrant atmosphere of Oahu with the luxury beaches of Maui, while others combine Kauai’s natural beauty with the volcanic landscapes of the Big Island. Hawaii also works exceptionally well as part of a wider USA itinerary, with popular combinations including Hawaii and California holidays or Hawaii and Las Vegas twin-centre trips. Our tailor-made Hawaii twin centre holidays are designed around your interests, with carefully planned flights, handpicked hotels and expert recommendations from our Hawaii specialists.

Hawaii Honeymoon Holidays

Hawaii is one of the world’s most romantic honeymoon destinations, offering luxury beachfront resorts, spectacular sunsets, private island experiences and breathtaking scenery across the Hawaiian Islands. Many couples choose Maui for its luxury hotels and relaxed atmosphere, while Kauai is perfect for secluded romance surrounded by lush tropical landscapes. Oahu combines luxury resorts with vibrant dining and nightlife, while the Big Island offers unique experiences including volcanoes, helicopter tours and stargazing.

For couples looking for privacy and romance, the Ritz-Carlton Oahu, Turtle Bay offers a more peaceful side of Oahu with dramatic coastal scenery, luxury accommodation and spectacular sunsets away from the crowds of Waikiki. For complete seclusion and barefoot luxury, our Hawaii honeymoon specialists often recommend Four Seasons Resort Lanai, one of Hawaii’s most exclusive resorts with stunning ocean views, exceptional service and a truly tranquil atmosphere. Maui is also incredibly popular for honeymoon holidays thanks to its luxury beachfront resorts, fine dining and scenic drives along the Road to Hana.

At Charter Travel, we create tailor-made Hawaii honeymoon holidays from the UK with luxury accommodation, island hopping itineraries and personalised experiences designed to make your honeymoon truly unforgettable.

Luxury Hawaii Holidays

Our luxury Hawaii holidays are designed for travellers seeking exceptional resorts, personalised service and unforgettable experiences across the Hawaiian Islands. From five-star beachfront hotels in Maui and Waikiki to exclusive luxury resorts on Kauai and the Big Island, we create bespoke itineraries tailored to your style of travel. Enjoy private ocean-view suites, world-class spas, fine dining, helicopter tours, sunset cruises and luxury island-hopping experiences. Whether you are celebrating a honeymoon, anniversary or special occasion, Charter Travel’s Hawaii specialists can create a tailor-made luxury holiday with premium flights, handpicked hotels and expert planning from start to finish.

Family Holidays to Hawaii

Hawaii is an incredible destination for families, combining beautiful beaches, outdoor adventures and family-friendly resorts across the islands. Oahu is especially popular for family holidays thanks to its safe swimming beaches, cultural attractions and activities suitable for all ages. Maui offers relaxed luxury and fantastic snorkelling opportunities, while the Big Island is ideal for adventurous families wanting to explore volcanoes, waterfalls and wildlife. At Charter Travel, we create tailor-made family holidays to Hawaii with spacious accommodation, multi-centre itineraries and carefully planned experiences designed around your family’s needs. From beach days in Waikiki to exploring tropical rainforests and marine life, Hawaii offers unforgettable experiences for every generation.

Hawaii Holidays From the UK

Planning a Hawaii holiday from the UK may seem complex, but our experienced travel specialists make the process seamless from start to finish. Most Hawaii holidays from the UK include a stopover in cities such as Los Angeles, San Francisco, Seattle or Vancouver before continuing to Honolulu or the neighbouring islands. Many travellers choose to combine Hawaii with California or Las Vegas to create an unforgettable twin-centre itinerary. At Charter Travel, we arrange flights, stopovers, hotels and island-hopping connections to create fully tailor-made Hawaii holidays from the UK. Whether you are looking for a luxury honeymoon, family holiday or multi-centre adventure, we can help design the perfect itinerary.

Our Hawaii Specialists Recommend

Best Luxury Hotels in Hawaii

Hawaii is home to some of the world’s most luxurious beachfront resorts, with each island offering a completely different experience. For ultra-luxury and exceptional service, our Hawaii specialists highly recommend the Four Seasons resorts across Maui and Lanai, known for their stunning oceanfront locations, world-class dining and relaxed Hawaiian elegance. The Westin resorts are perfect for travellers looking for luxury combined with family-friendly facilities and excellent beachfront locations, especially on Maui and Oahu. On the Big Island, the Fairmont Orchid offers a fantastic blend of luxury, authentic Hawaiian atmosphere and incredible coastal scenery. For travellers seeking luxury on more manageable budgets, Hilton Hawaiian Village in Waikiki remains one of the best-value resorts in Hawaii thanks to its beachfront setting, extensive facilities and excellent location for exploring Oahu.

Best Hawaiian Island Combinations

Choosing the right island combination is one of the most important parts of planning a tailor-made Hawaii holiday. For first-time visitors, Oahu, Maui and Kauai offer the perfect balance of vibrant city life, luxury resorts and authentic Hawaiian scenery. Oahu combines iconic Waikiki beaches, nightlife and cultural attractions, while Maui offers luxury resorts, beautiful beaches and incredible coastal scenery. Kauai is ideal for travellers wanting lush landscapes, waterfalls and a more peaceful atmosphere. Nature lovers will particularly enjoy Maui and Kauai thanks to their snorkelling, rainforest hikes and dramatic scenery. For a more authentic Hawaiian feel, the Big Island and Kauai are excellent choices, offering volcanoes, black sand beaches, local farms and charming boutique stays. Travellers looking for a more modern luxury experience often prefer combining Maui and Oahu, where you will find some of Hawaii’s best luxury resorts, restaurants and beachfront experiences. 

Best First-Time Hawaii Itinerary

For first-time visitors to Hawaii, our specialists usually recommend a Hawaii island-hopping itinerary combining Maui, Oahu, Kauai and the Big Island, with around four to five nights on each island. This allows travellers to experience the incredible diversity Hawaii has to offer, from the beaches and nightlife of Waikiki to the waterfalls of Kauai, the luxury resorts of Maui and the volcanic landscapes of the Big Island. It is the ultimate bucket-list Hawaii holiday and one of the best ways to fully experience the Hawaiian Islands. Returning visitors often prefer spending longer on fewer islands to enjoy a slower pace. Oahu and Kauai create a fantastic contrast between vibrant city life and peaceful natural beauty, while Maui and Oahu are ideal for travellers seeking a more luxury-focused Hawaii holiday with exceptional resorts, dining and beaches.

Hidden Gems in Hawaii

Beyond Hawaii’s famous beaches and resorts, there are countless hidden gems that make a tailor-made Hawaii holiday truly unforgettable. On Maui, many travellers drive the Road to Hana in a single day, but our Hawaii specialists strongly recommend staying overnight in Hana to experience the quieter side of Maui and fully enjoy the waterfalls, rainforest scenery and black sand beaches without rushing. On Oahu, some of the island’s best local food can be found at small food trucks serving authentic Hawaiian dishes away from the main tourist areas. Adventurous travellers should also visit the famous Green Sand Beach on the Big Island or explore Maui’s striking black sand beaches along the Hana coastline. For one of the most unforgettable experiences in Hawaii, we highly recommend a helicopter tour over Kauai or the Big Island to see hidden waterfalls, dramatic cliffs and volcanic landscapes that cannot be reached by road.

Insider Tips From Our Hawaii Specialists

Booking your Hawaii holiday early is one of the best ways to secure lower prices on flights and luxury resorts, especially during peak travel periods and school holidays. Travellers looking to reduce costs on Oahu can often save significantly by staying around Honolulu Harbour rather than directly on Waikiki Beach while still remaining close to the main attractions. If you are planning to drive the famous Road to Hana in Maui, book the iconic Mama's Fish House at least 6 months prior to arrival to ensure you get to experience this beloved Maui restaurant! Our travel specialists also recommend considering flights via Seattle rather than the more popular Los Angeles or San Francisco, as these routes can sometimes offer better value and cheaper flight prices from the UK. With careful planning and expert advice, it is possible to create a tailor-made Hawaii holiday that balances luxury, value and unforgettable experiences across the islands.

Hawaii Holidays FAQs

How much does a Hawaii holiday cost from the UK?

The cost of a Hawaii holiday from the UK depends on the time of year, length of stay, hotel standard and number of islands you visit. As a guide, tailor-made Hawaii holidays typically start from around £2,500–£5,000 per person including flights and accommodation for a two-week trip. Luxury Hawaii holidays and honeymoon itineraries with five-star beachfront resorts can cost significantly more, especially during peak travel seasons. Island-hopping holidays across Oahu, Maui, Kauai and the Big Island are one of the most popular ways to experience Hawaii and can be tailored to suit a range of budgets and travel styles.

Which Hawaiian island is best for first-time visitors?

Oahu is generally considered the best Hawaiian island for first-time visitors thanks to its mix of iconic beaches, luxury resorts, nightlife, culture and famous attractions including Waikiki and Pearl Harbor. However, many travellers choose a multi-centre Hawaii holiday combining Oahu with Maui or Kauai to experience a wider variety of landscapes and experiences. Maui is ideal for luxury and honeymoon holidays, while Kauai is perfect for nature lovers looking for waterfalls, hiking and dramatic scenery.

How long should I spend in Hawaii?

For a first-time Hawaii holiday from the UK, we usually recommend spending at least 10 to 14 nights across two to four islands. Hawaii is a long-haul destination, so a longer stay allows you to fully experience the islands at a relaxed pace. Many travellers spend four to five nights on each island during an island-hopping itinerary, combining destinations such as Oahu, Maui, Kauai and the Big Island. If you are returning to Hawaii, spending a week on two islands can offer a more relaxed and immersive experience.

Do UK travellers need an ESTA for Hawaii?

Yes, UK travellers visiting Hawaii must usually apply for an ESTA before travelling to the United States, as Hawaii is a US state. ESTA stands for Electronic System for Travel Authorisation and is required for most British passport holders travelling to the USA for tourism purposes under the Visa Waiver Program. Travellers should apply before departure and ensure their passport meets the latest US entry requirements

Is Hawaii good for honeymoon holidays?

Hawaii is one of the world’s most popular honeymoon destinations thanks to its luxury resorts, spectacular beaches, scenic landscapes and romantic atmosphere. Maui is particularly popular for honeymoon holidays due to its luxury beachfront hotels, fine dining and stunning coastal scenery, while Kauai offers a more secluded and peaceful experience surrounded by lush tropical landscapes. Couples often choose island-hopping honeymoons combining Maui, Oahu and Lanai for the perfect mix of luxury, adventure and relaxation.

Which island is best for families?

Oahu is often considered the best Hawaiian island for families thanks to its family-friendly beaches, wide choice of resorts, activities and attractions suitable for all ages. Waikiki offers calm swimming beaches, shopping, dining and easy access to excursions including Pearl Harbor and snorkelling trips. Maui is another excellent option for family holidays thanks to its relaxed atmosphere, luxury family resorts and fantastic beaches. Families looking for adventure often enjoy the Big Island with its volcanoes, waterfalls and outdoor activities.

Can you island hop in Hawaii?

Yes, island hopping is one of the best ways to experience Hawaii and is highly recommended for first-time visitors. Frequent inter-island flights make it easy to combine islands such as Oahu, Maui, Kauai and the Big Island within one tailor-made itinerary. Each island offers a completely different atmosphere and landscape, from the beaches and nightlife of Waikiki to the waterfalls of Kauai and the volcanic scenery of the Big Island. Our Hawaii specialists can create seamless island-hopping holidays from the UK with flights, hotels and personalised itineraries included.

What is the cheapest month to visit Hawaii?

Generally, the cheapest times to visit Hawaii are during the shoulder seasons, particularly April to early June and September to mid-November. During these periods, flights and hotels can often offer better value compared to peak holiday seasons such as Christmas, New Year and summer school holidays. Booking early is also one of the best ways to secure lower prices on flights and accommodation, especially for luxury resorts and island-hopping holidays.

Is Hawaii expensive?

Hawaii is considered a premium long-haul destination, particularly compared to many Caribbean or European beach holidays. However, there are ways to make a Hawaii holiday more affordable without compromising the experience. Choosing mixed hotel categories, travelling during shoulder seasons and staying slightly outside premium beachfront locations can significantly reduce costs. Resorts such as Hilton Hawaiian Village on Oahu offer excellent value for travellers seeking a balance between location, facilities and affordability. Tailor-made Hawaii holidays can also be designed to suit a wide range of budgets.

Can I combine Hawaii with California or Las Vegas?

Yes, combining Hawaii with California or Las Vegas is one of the most popular ways to create a multi-centre USA holiday from the UK. Many travellers choose to spend time in Los Angeles, San Francisco or Las Vegas before continuing to Hawaii, creating an itinerary that combines cities, beaches and island experiences in one trip. Hawaii and California holidays are particularly popular for first-time visitors, while Las Vegas and Hawaii combinations are ideal for travellers looking to combine entertainment, luxury hotels and tropical relaxation.

How long is the flight from the UK to Hawaii?

There are currently no direct flights from the UK to Hawaii, so most journeys include a stopover in cities such as Los Angeles, San Francisco, Seattle or Vancouver. Total travel time from the UK to Hawaii is typically around 17 to 22 hours depending on flight routes and connection times. Many travellers choose to include a stopover in the USA as part of a twin-centre holiday, allowing them to break up the journey and explore destinations such as California or Las Vegas before arriving in Hawaii.