The Hawaiian Islands have it all—from palm-fringed bays and dramatic cliffs to incredible marine life and a unique, ancient culture. Experience four of these picture-perfect islands aboard a 36-guest boutique yacht. With everything you need on board the ship—kayaks, paddle boards, snorkel gear, and hiking poles—you'll be totally equipped to immerse yourself in the land of aloha. On magical Moloka'i, enjoy a cultural lesson in poi making or choose a hike to a waterfall in Halawa's cathedral valley. Explore towering sea cliffs, volcanic plugs, and the famed sweetheart rock on the private island of Lana'i. Kayak or snorkel among coral gardens in a sea turtle habitat off West Maui, and anchor offshore of the big island with a chance to go for a night swim with Giant Pacific Manta rays. In the evenings, settle into the laid-back spirit of Hawaii while you watch for dolphins out in the Pacific.
Arrive: Molokai, Hawaii (or reverse)
Depart: Kailua-Kona, Hawaii (or reverse)
Note: This trip is not exclusive to, nor operated by, Wilderness Travel, who acts solely as an agent in booking your reservation with the operator. Please download the Rate Sheet in the Dates & Pricing section to see the full pricing details and contact our Cruise Collection Specialists to check availability.
Welcome to Hawaii! You'll be transferred to our hospitality area in Kailua. Later, the captain and crew greet you with smiles and champagne as you board the awaiting Safari Explorer. This evening, settle in and enjoy dinner aboard the yacht, before a presentation about your week ahead.
On embarkation day, your flight should arrive no later than 2:00 pm
Kealakekua Cove, known as a premier snorkeling and kayaking destination in the Hawaiian Islands, is also the historic site of the Cook Monument, marking where Captain Cook met his end in February 1779. Here, you can encounter vibrant marine life, including tropical fish, sea turtles, and possibly dolphins. Enjoy these activities in this picturesque bay before we depart after lunch. In the afternoon, we set off on a Marine Mammal Search, potentially taking us to the remote South Point area.
This morning, join us on a rocky hike up the cool and misty slopes of Hualalai Volcano. Explore our private trail at 6,500 ft above the Kona coast with your own naturalist guide. Cross surreal scenes of black lava flows, pass pit craters and stroll through native dryland forest. You’ll discover a lava tube and learn how lava flows from the early 19th century reshaped the coastline below you. This evening you'll anchor at an offshore location to search for and night snorkel with Giant Pacific Manta rays. This excursion offers snorkelers the opportunity to observe these majestic animals up close and personal. Marine life is often within inches, offering a unique experience with wild animals in their environment. Strict guidelines are followed to lessen any disturbance of these beautiful creatures.
Today we snorkel among coral gardens teeming with underwater life and a known sea turtle habitat called “Turtle Town.” The Humpback National Marine Sanctuary located between Lana’i, Molokai, and Maui provides front-row seats as you cruise through these productive breeding grounds searching for dolphins, whales, and other marine life. Look above and below the surface.
Gear up for a day of play on the “Private Island.” Snorkel far away from the crowds this morning along the coastline of Lana'i. Thousand-foot sea cliffs line the shore and ancient volcanic plugs sit both above and below the water’s surface and play host to a wide diversity of marine life. Suit your fancy and the weather - explore Lana’i village, hike, or take a bike excursion.
Embark on an unforgettable trip to the captivating seascapes of Hawaii. Your day may include a kayaking adventure along Maui's hidden coves, paddling through turquoise waters, and discovering the untouched beauty of its coastline. Transition to Lana'i, where kayaking takes you to remote areas between the cerulean ocean and lush greenery. You may cruise along Moloka'i's dramatic northern cliffs, experiencing the awe-inspiring vista of soaring precipices and an occasional frolicking dolphin. As the day unfolds, enjoy cruising for critters and charismatic sea life from the top deck, savoring some of our signature drinks while expert naturalist guides introduce you to the rich marine life and bird species that call these waters home. Today, each experience we choose is a brushstroke on the canvas of your memory, showcasing the beauty that makes Hawaii's seascapes truly extraordinary.
A warm aloha spirit gives you a sense of Hawaii long ago. No stop lights, no high-rises, just a welcome slower pace. “Talk story” with locals and experience their land and traditions as few visitors do. You’ll hear legends and lore, then take in a cultural lesson in taro patches and poi making, or hike to a towering waterfall in Halawa’s cathedral valley, one of the island’s most historic places. This evening, enjoy an evening pa?ina (feast), complete with a home-style Hawaiian jam session.
After one more Hawaiian breakfast, you'll be transferred to the Molokai Airport.
On disembarkation day your flight should leave no earlier than 10:00AM
Day 1 Molokai / Embarkation
On embarkation day, your flight should arrive no later than 3:30PM
Day 2 Molokai
Day 3 Captain's Choice
Day 4 Lana'i City
Day 5 Maui
Day 6 Big Island
Day 7 Big Island
Day 8 Kailua-Kona / Disembarkation
On disembarkation day, your flight should leave no earlier than 12:00PM
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
The trip is rated Level 1, Easiest, and is appropriate for anyone in good health who is physically active.
"An amazing way to see the natural beauty of Hawaii, its marine wildlife, and to explore its history and culture. Molokai and Lanai were unexpectedly delightful. Excellent snorkeling and humpback whales everywhere. Just a dream vacation!"
Grant G.
Cleveland, OH
"We absolutely loved it—it was all very well organized, and we would recommend Wilderness Travel to anyone in the future. Great trip!"
Simon R.
Denver, CO
Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
Submit the form below to download itinerary
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult.