Hawaii Island Hopping

9 Nights & 10 Days

Oahu > Big Island > Maui

There is variety between each of the Hawaiian Islands, each having a deep sense of their own personality. We know the best way to get the best from your trip – visiting the right islands in the right order, seeing the right sites and meeting the right people.



Today you will arrive on the beautiful island of Oahu. Like Honolulu-born former President Obama, Oahu is proud of its multicultural heritage, and through it pulses the lifeblood of Hawaiian traditions. Here you can surf the North Shore’s giant waves, hike atop knife-edged pali (cliffs), dive into Hanauma Bay’s outdoor fishbowl, go windsurfing or kayak to uninhabited islands off Kailua – and still be back in Waikiki for sunset drinks. Your Hawaiian adventure will start from here!

Upon arrival, your driver will be waiting for you and will assist you with your luggage to your waiting vehicle. From here he will take you to your hotel for check-in. You will have the rest of the day to relax at the hotel. Head into Waikiki (main tourist/shopping district) if you are looking for some nightlife or evening entertainment.

Overnight at The Kahala Hotel and Resort


This morning your driver-guide will pick you up at the Kahala Resort for a full day tour of Oahu (9-5pm, approximately).

First, head to the North Shore one of the most iconic parts of the Hawaiian Islands. If there is such a thing as a perfect wave, you’ll likely find it on Oahu’s North Shore. The big, glassy winter waves of this legendary surf mecca attract the best surfers in the world! Stretching for more than 7 miles, the beaches of the North Shore host the world’s premier surfing competitions during the peak winter months. Here your guide will bring you to one of the top beaches for a Surfing Lesson or you can visit small tributaries for Stand Up Paddle (SUP) Board Lesson (one lesson per person included).

After your lesson, head to Haleiwa Town, where you can shop, have a local lunch and cool off with rainbow flavored shave ice.

In the afternoon begin your trip back towards Honolulu where you have the late afternoon and evening free to enjoy at leisure.

Overnight at The Kahala Hotel and Resort


Enjoy breakfast at your hotel and check out. Then, accompanied by your expert guide (and taking your luggage with you), go on a half-day tour of Pearl Harbor and the Arizona Memorial, the final resting place for the 1,102 U.S. sailors and Marines killed during the surprise attack by Japanese forces on December 7, 1941 that secured U.S. involvement in World War II.

The memorial is a stark reminder of the sacrifices made by the men and women of the U.S. armed forces to protect American freedoms. During your tour, your guide will paint the picture of what happened on that fateful day on the walk of remembrance and at the two memorial museums. During this time you will discuss the events leading up to the War, the attack itself, and significant battles during the war.

Head to the airport to catch your flight to Big Island. Upon landing at the airport, your driver will meet you at the baggage claim and take your to your hotel.

The Big Island is as large as the other Hawaiian islands combined. This is the place where not only the raw creation occurs, but also the dizzying diversity. The rest of the day is at your leisure to relax.

Overnight at Fairmont Orchid


This morning you will be picked up and brought to the east side of the island- to Hilo to begin your volcano adventure (estimated drive time is two hours). Upon arrival at the heliport, check-in for your helicopter ride above the volcanoes! After landing you will meet your expert driver-guide who will take you on a journey through the remote and rugged landscape of Kaʻū — home to Hawai’i Volcanoes National Park, historic farming plantations and the famous black sand beach of Punaluʻu. Some of the highlights of your private tour include:

  • Discover all the “must-see” spots within the Park; including Jaggar Museum, Nāhuku (Thurston Lava Tube) and Halema‘uma‘u Crater
  • Immerse yourself in stories of Hawaiian legends and mythology, with a focus on Pele, the Hawaiian goddess of fire, lightning, wind and volcanoes
  • Lunch at the Volcano House – Perched on the edge of the Kilauea Crater

After touring your driver will drive you back across the island, back to the Kona side where your resort is located.

Have the rest of the evening at leisure.

Overnight at Fairmont Orchid


Have the morning free to relax at the hotel.

In the evening, board your private catamaran and set sail in time to view the beautiful Kona sunset. Your boat will offer ample seating, lighting and bathrooms. After the sun sets and you’ve had time to take in the scenery, you will prepare for a private night snorkel adventure. You will need to wear a swimsuit and a wetsuit top will be provided.

The manta ray is among the largest fishes in the ocean with wingspans of up to 20 feet and more. The Kona Coast offers the best opportunity to encounter these amazing creatures. At night, spotlights are used to attract mantas that feed off the plankton illuminated by the light. As intimidating as these otherworldly mantas look, they are actually quite friendly and do not have stingers.

After an hour swims with these beautiful creatures, you will return to the Kailua pier in the evening.

Overnight at Fairmont Orchid


The morning is at your leisure to do as you please.

In the early afternoon, you will be transferred to the airport in time for your flight to Maui. Upon landing, your car and driver will take you to your hotel.

After checking in and freshening up, the rest of the day is at your own leisure.

Overnight at Fairmont Kea Lani


Early this morning your driver-guide will pick you up for a day of adventure and incredible sights along the Road to Hana and looping around the entire mountain! First, if hungry, you will make a stop breakfast at a local favorite. Along the Road to Hana, your guide will make numerous stops, providing ample time to explore the highlights of Ke’anae Peninsula, Hanawi waterfall and the black sand beach at Wai’anapanapa.

Enjoy freshly baked banana bread while taking in the remote coastline views and make a stop for lunch in the open-air dining room at Travaasa Hana Hotel. The views on this trip are stunning and will provide endless sights for waterfalls, pristine valleys and spectacular seascapes. There is also an opportunity for swimming and short walks by various loop trails.

Arrive back at your hotel at around 5:00 PM. The rest of the evening is at your leisure.

Overnight at Fairmont Kea Lani


Today you will explore the magnificent Turtle Town on a private kayaking tour. After a water safety and paddling orientation, depart from beautiful Makena Landing in the heart of Turtle Town. As you glide across the pristine clear waters you’ll enjoy stunning views of Haleakala summit, Molokini Crater, Pu`u Olai, the Makena/Wailea coastline and surrounding Islands, including the Big Island on a clear day! Along the journey you will  stop at one of the many snorkel spots Turtle Town has to offer so you can begin to explore this incredible underwater world! This area offers unique reef structures and underwater caves and turtle sightings are guaranteed!

Once you return to your hotel, your afternoon is at leisure.

At 5:00 PM, your driver will then pick you up and bring you to the West Side of Maui for an authentic Hawaiian luau. A luau s a traditional Hawaiian party that is usually accompanied by vibrant entertainment and delicious, traditional food such as poi, kalua pig, poke, lomi salmon, opihi, haupia and beer. Of course the luau would not be complete without traditional Hawaiian music and hula!

When you arrive for the luau, you will be greeted with a fresh flower lei and shown to your own private table. For dinner tonight is a multi-course meal inspired by the culture and traditions of Polynesia. Each course represents a modern twist on traditional island cuisine as you are treated to four courses each representing a different island culture. For many visitors the highlight of a Maui luau is the amazing Samoan fire knife dance. Brave performers will treat you to death defying feats of astonishing dexterity as they pass the flaming knife through their legs and behind there backs, giving you a perfect send off for a perfect evening!

Overnight at Fairmont Kea Lani


Your final full day in Hawaii is at your own leisure to relax.

In the evening, enjoy expansive unobstructed views of the beautiful Maui coastline during a private sunset cruise. You will meet your captain at the beach for boarding. This experience begins approximately 3 hours prior to sunset so that you may enjoy a full spectrum of colors as the sky transitions into night. During this leisurely cruise, you will be able to escape the hustle of the city and relax as you sail on calm waters.

Overnight at Fairmont Kea Lani


After you check out of your hotel, your car and driver will be waiting for you to take you to the airport in time for your flight home.


This pre-designed itinerary can be booked as is or be completely customized to your tastes. You can change details like upgrading accommodation or adding extra nights and excursions to suit your budget, interests and needs.


  • Learn to surf or stand-up paddleboard on Oahu’s legendary North Shore
  • Explore Pearl Harbor and the Arizona Memorial with your expert guide
  • Helicopter over Hawaii’s volcanos …with the doors open!
  • Swim with manta rays on a private sunset catamaran sail
  • Swim beneath waterfalls and hike the legendary Road to Hana
  • Kayak and snorkel Turtle Town before heading to an authentic luau
  • Cruise the Maui coastline at sunset on a private yacht