Hawaii Island Hopping Holidays

Discover More with a Three-Island Hawaiian Getaway

If you’re ready for a more immersive Hawaiian experience, consider combining three islands. Here are two standout combinations:

• Maui, Oahu, and Big Island: This option is perfect for those looking to experience diverse landscapes and activities. Start with Oahu’s vibrant city life, then move on to Maui’s laid-back luxury and breathtaking coastlines. Finish your trip on the Big Island, where you can explore the awe-inspiring volcanic landscapes, lush rainforests, and star-studded skies of Mauna Kea. Three islands, each offering unique experiences, create the ultimate Hawaii adventure for those with a bit more time to spare.
• Oahu, Kauai, and Maui: A great combination for those seeking both natural beauty and some traditional cultural experiences. Oahu’s history and vibrant atmosphere contrast beautifully with the tranquil, lush landscapes of Kauai. Maui ties it all together with its diverse offerings—from beaches and volcanoes to charming towns. You’ll get a healthy balance of city life, stunning natural beauty, and adventurous activities with this option.

Combine All Four Islands for the Ultimate Hawaii Island Hopping Holiday

For the ultimate island-hopping experience, why not explore all four of Hawaii’s major islands? Oahu, Maui, Kauai, and the Big Island offer a wide range of activities, scenery, and cultures that make for an extraordinary trip.

• Oahu, Maui, Kauai, and the Big Island: From the lively streets of Honolulu to the serene beaches of Kauai, the volcanic wonders of the Big Island, and the picturesque beauty of Maui, combining all four islands ensures you experience the very best that Hawaii has to offer. This option is ideal for those with a sense of adventure, as it allows you to explore different landscapes, from tropical rainforests and arid deserts to volcanic craters and coral reefs. Each island brings something new, making it the perfect way to truly immerse yourself in the magic of Hawaii.

Hawaii Island Hopping is a fantastic way to see more than one of the Hawaii islands, if you are considering a holiday to Hawaii but are struggling to decide between the Islands, why choose? Let our knowledgeable and specialist team at Tailormade Hawaii help to create that unforgettable, once in a life-time, Hawaii Island Hopping holiday. Whether you're looking to soak up the sun on pristine beaches, explore dramatic volcanic landscapes, or experience rich Hawaiian culture, we have the perfect holiday for you.

Oahu: The Heart of Hawaii

Oahu, known as "The Gathering Place," is home to Hawaii's vibrant capital city, Honolulu. This island offers a mix of history, culture, and outdoor adventures. Why not hike the iconic Diamond Head crater for panoramic views of Waikiki Beach, visit Pearl Harbor and immerse yourself in American history, and relax on the world-famous beaches, including Waikiki and Ala Moana Beach Park.

Top 3 Oahu Highlights:

• Waikiki Beach: Enjoy sunbathing, surfing, and shopping in the heart of Honolulu.
• North Shore: Witness legendary surf waves and explore charming beach towns.
• Hanauma Bay: Snorkel in a protected marine embayment, home to abundant sea life.

Hotel Options on Oahu:

1. The Royal Hawaiian: A luxury resort with a historical touch, located on Waikiki Beach.
2. Alohilani Resort Waikiki Beach: Modern amenities with stunning ocean views.
3. The Kahala Hotel & Resort: A more secluded option with top-tier service and a private beach.

Maui: The Valley Isle

Maui, often considered the most romantic of the Hawaiian islands, boasts a stunning mix of lush rainforests, volcanic landscapes, and pristine beaches. We highly recommend driving the scenic Hana Highway, with waterfalls, black sand beaches, and panoramic views. Make sure to explore the Haleakalā National Park and watch the sunrise from the top of a dormant volcano, and snorkel with sea turtles and vibrant fish at Molokini Crater.

Top 3 Maui Highlights:

• Road to Hana: A winding journey through tropical rainforests, waterfalls, and hidden beaches.
• Lahaina Town: A charming historic town with art galleries, shops, and whale watching.
• Kaanapali Beach: A beautiful spot for sunbathing, swimming, and sailing.

Hotel Options on Maui:

1. Four Seasons Resort Maui at Wailea: An upscale, beachfront resort with world-class amenities.
2. The Ritz-Carlton, Kapalua: A luxury property nestled in the lush Kapalua Bay area.
3. Montage Kapalua Bay: Perfect for those seeking an indulgent and relaxing beachfront escape.

Big Island: The Island of Adventure

The Big Island, also known as Hawaii Island, is a land of contrasts with volcanic landscapes, lush rainforests, and tranquil beaches. Whilst on the Big Island be sure to visit Hawai'i Volcanoes National Park and experience active volcanic landscapes. Then, relax on the beautiful black sand beaches of Punalu'u Beach Park and discover the charm of the Waipi’o Valley, a lush, secluded area ideal for hiking and scenic drives.

Top 3 Big Island Highlights:

• Kilauea Volcano: Experience the active lava flows and dramatic landscapes.
• Akaka Falls State Park: Visit these stunning waterfalls set in a tropical rainforest.
• Mauna Kea Summit: Take a stargazing tour at one of the world’s best astronomical observation spots.

Hotel Options on Big Island:

1. Four Seasons Resort Hualalai: An exclusive, luxurious beachfront resort near Kona.
2. Mauna Lani, Auberge Resorts Collection: Ideal for those seeking peace and luxury with a deep connection to nature.
3. Hilton Waikoloa Village: A family-friendly resort with tropical gardens and a private lagoon.

Kauai: The Garden Isle

Kauai, often referred to as “The Garden Isle,” is the oldest and most lush of the Hawaiian islands, offering a tranquil retreat amidst verdant landscapes. Whilst on Kauai be sure to explore the stunning Na Pali Coast by boat or hiking trail, kayak the Wailua River and visit the beautiful Wailua Falls, and take a scenic drive to Waimea Canyon, known as the “Grand Canyon of the Pacific.”

Top 3 Kauai Highlights:

• Na Pali Coast: Stunning cliffs and secluded beaches, accessible by foot, boat, or helicopter.
• Hanalei Bay: A picture-perfect crescent-shaped beach with great surfing and calm waters.
• A haven for hiking with panoramic views of the island.

Hotel Options on Kauai:

1. A luxurious resort surrounded by tropical gardens and ocean views.
2. The Westin Princeville Ocean Resort Villas: Perfect for those seeking a blend of home-like comfort and resort luxury.
3. A boutique resort with modern amenities and beachfront relaxation.

Lanai: The Pineapple Isle

Lanai, often referred to as the "Pineapple Isle," is a small yet extraordinary destination that offers an intimate escape from the more popular Hawaiian islands. With its serene beaches, rugged landscapes, and luxurious resorts, Lanai is perfect for those looking for peace, seclusion, and a true island retreat. On Lanai, be sure to explore the otherworldly landscapes of Shipwreck Beach, where the remains of an old vessel rest on the shore. Visit the Garden of the Gods, a unique rock formation that offers stunning views of the island and beyond, and take a guided tour of the Lanai Pineapple Plantation, where you can learn about the island’s history and heritage.

Top 3 Lanai Highlights:

• Shipwreck Beach: A striking, remote beach that features the rusted remains of a ship and great views.
• Garden of the Gods: An otherworldly landscape of red and black rocks that make for an unforgettable experience.
• Lanai City: A charming, peaceful town offering art galleries, unique boutiques, and local dining options.

Hotel Options on Lanai:

1. Four Seasons Resort Lanai: A luxurious, high-end resort set on the island's southern coast with world-class amenities and stunning ocean views.
2. Hotel Lanai: A charming, intimate boutique hotel located in Lanai City, perfect for those seeking a peaceful getaway.
3. Sensei Lanai, A Four Seasons Resort: A wellness-focused resort offering immersive experiences that help you unwind and rejuvenate in a tranquil setting.

Tailormade Hawaii is Charter Travel's dedicated Hawaii website. Charter Travel is a member of both ABTA and ATOL so you may book with complete peace of mind, knowing that your money is safe with us. As registered Hawaiian specialists with the Hawaiian Tourist board and a specialist agent for a number of Hawaiian hotels we are able to provide our clients with many little extra features not usually available to other agents - we welcome the opportunity to be part of your plans.