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Holidays

Thinking of a Hawaii Holiday? Let’s Make It Happen!

Dreaming of a tropical escape in 2025 or 2026? You're not alone — Hawaii continues to be one of the most sought-after holiday destinations in the world. With jaw-dropping scenery, luxury resorts, and unique experiences across six stunning islands, it's the perfect place to unwind, explore, and make unforgettable memories.

Why Book with Tailormade Hawaii?

At Tailormade Hawaii, we’re Hawaii specialists — it’s what we do every day! Our expert team has years of hands-on experience exploring the islands, finding the best hotels, and uncovering hidden gems to make your trip truly special.

  • We tailor each trip around your dream Hawaii experience
  • Access to exclusive hotel perks and offers
  • ATOL and ABTA protected — book with confidence
  • We’re official Hawaiian specialists with the Hawaiian Tourist Board

Flights Made Easy

We work closely with trusted airline partners like Virgin Atlantic, British Airways, American Airlines, United and Hawaiian Airlines to bring you:

  • The best fares on flexible routes
  • Stopover options to break up the journey
  • Seamless multi-island itineraries

Make the Most of a Stopover

Hawaii is about a 5-hour flight from the US mainland — so why not turn that into part of the adventure?

  • Popular stopovers: Los Angeles, San Francisco, San Diego, Las Vegas
  • Other options: New York or Vancouver
  • Perfect chance to tick off iconic American cities on the same holiday!

Six Islands, Endless Experiences

Each of Hawaii’s six main islands offers something completely unique. Why visit one when you can explore more?

  • Oahu – Iconic Waikiki Beach & historic Pearl Harbour
  • Maui – Dramatic coastlines & romantic resorts
  • Big Island – Volcanoes, black sand beaches & epic hikes
  • Kauai – Lush landscapes & jaw-dropping waterfalls
  • Lanai & Molokai – Peaceful, authentic escapes

Island hopping is easy with frequent inter-island flights from Hawaiian Airlines. We’ll handle all your transfers or set you up with a hire car if you’d rather explore at your own pace.

Weddings, Honeymoons & Special Celebrations

Planning a honeymoon, wedding, vow renewal, or anniversary in 2025/2026? We’ve got you covered:

  • Expertly arranged beach weddings — ceremony, venue, and paperwork
  • Special honeymoon packages and resort perks
  • Free vow renewal arrangements for our clients
  • Option to marry on one island, honeymoon on another!

With an average year-round temperature of 27°C, Hawaii is the ideal destination any time of year — perfect for fitting around school breaks or annual leave.

Cruise & Stay Options

Want to explore the islands in comfort and style? Ask us about cruise and stay holidays, including:

  • The award-winning Pride of America by Norwegian Cruise Line
  • 7-night cruises paired with luxury pre- or post-cruise resort stays

Let’s Plan Your Trip

Whether you're booking a once-in-a-lifetime honeymoon, planning a multi-island adventure, or just want to unwind in paradise — our expert team is ready to help.

  • We’ll help you find the best value for your 2025/2026 Hawaii holiday
  • Everything can be 100% tailored to your preferences
  • Call or email us anytime for free advice — no obligation

Tailormade Hawaii is part of Charter Travel, an ABTA and ATOL-protected company — giving you total peace of mind when booking.

Your Dream Hawaii Holiday Starts Here

We can't wait to help you start planning! Let us turn your ideas into a personalised itinerary filled with unforgettable moments.

Explore Holidays

Oahu Holidays
Oahu is also known as the 'Gathering Place' and is home to the majority of Hawaii's residents. It is also the island where you will find the world famous Waikiki Beach, Pearl Harbour and Diamond Head.
The Big Island
Big Island is the largest of the Hawaiian Islands, and is also the youngest. The volcanic activity that created the Hawaiian Islands continues to this day, constantly shaping and reshaping the island.
Kauai Holidays
Situated just 20 minute flight from Oahu Island, Kauai offers both crystal clear blue waters of the Pacific Ocean and is a true natural spectacle, referred to as the 'Garden Isle'
Maui Holidays
Maui has a selection of beaches considered to be amongst the finest in the world. Our holidays to Maui will make you fall in love with this beautiful island