Big Island, Maui, Lanai, and Molokai aboard the Safari Explorer
Hawaiian Seascapes
BOOKING DISCOUNT
- 15% off all cabins on select 2025 & 2026 departures
Overview
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)
Highlights
- Search for dolphins, whales, and other marine life during voyages, visit the Humpback National Marine Sanctuary—located between Lanai, Molokai, and Maui
- Snorkel in pristine Hawaiian waters, including Olowalu on Maui and Kealakekua Bay on the Big Island
- Savor a pa'ina (feast), “talk story” with locals, and experience their land and traditions as few visitors ever do
Itinerary
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 on Moloka'i. 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.
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 ever 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. At the Moloka'i Museum, discover the history of this ancient homeland as you enjoy an evening pa'ina (feast), complete with a home-style Hawaiian jam session.
Gear up for a day of play on the “Private Island.” Thousand foot sea cliffs line the shore and ancient volcanic plugs sit both above and below the water's surface as host to a wide diversity of marine life. Snorkel, paddle board, kayak, explore by skiff, or stretch your legs on hike—whichever activities suit your fancy. Take a stroll to Sweetheart Rock, a sea stack jutting 80 feet above the crashing surf, and discover the legend of the princess Puu Pehe. Learn about the islands plantation days with a visit to the quaint Lanai Culture and Heritage Center.
In ancient times, Olowalu was considered a place of refuge. Today, it delivers a treat of snorkeling among coral gardens teeming with underwater life and a known sea turtle habitat. The Humpback National Marine Sanctuary—located between Lanai, Molokai, and Maui—provides front-row seats as you cruise through these productive marine breeding grounds searching for dolphins, whales, and other marine life.
Leave it to your Captain and crew to seek out and unveil the best opportunities the islands hold in store today. Dramatic volcanic backdrops, marine life sightings, and chances for snorkeling, kayaking, and paddle boarding are all possible!
Snorkel, kayak, or swim in crystal-clear waters off the Kona coast. Depending on weather and your mood, spend the day in the water or you can explore the rugged coastline on a skiff ride. This evening you'll anchor at an offshore location to 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.
This morning, take a rocky hike up the cool and misty slopes of Hualalai Volcano and explore a private trail at 6,500 feet 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 re-shaped the coastline below you. Enjoy magnificent vistas and walk amid stunning lava formations in a forest of native birdsong.
For your final afternoon, relax onboard or go for one last dip. This evening celebrate with the Captain's Dinner and photographic recap of your adventure.
For your final afternoon, relax onboard or go for one last dip. This evening celebrate with the Captain's Dinner and photographic recap of your adventure.
As the Safari Explorer docks at Kawaihae Harbor, you'll be transferred to the Kona Airport or to your extended UnCruise hotel stay.
Day 1 Arrive Kailua-Kona / Embarkation
Molokai to Molokai Summer Itinerary-in-Brief (July-August) This departure will sail roundtrip from Molokai and take advantage of the warmer water and gentle trade winds of summer, offering the opportunity to see the north shore of the islands whenever possible.
Day 1 Molokai / Embarkation
Day 2 Hanomalino Bay
Day 3 Kealakekua Bay / Kailua-Kona
Day 4 Captain's Choice Exploration
Day 5 Lana'i
Day 6 Olowalu / West Maui
Day 7 Molokai
Day 8 Molokai / Disembarkation
Molokai to Molokai Summer Itinerary-in-Brief (July-August) This departure will sail roundtrip from Molokai and take advantage of the warmer water and gentle trade winds of summer, offering the opportunity to see the north shore of the islands whenever possible.
Day 1 Molokai / Embarkation
Day 2 Captain's Choice
Day 3 Lana'i
Day 4 Kallua-Kona
Day 5 Hawai'i, The Big Island
Day 6 Olowalu / West Maui
Day 7 Halawa Valley
Day 8 Molokai / Disembarkation
Accommodations
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
What the Trip is Like
The trip is rated Level 1, Easiest, and is appropriate for anyone in good health who is physically active.
Client Testimonials
"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
Book your trip today
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!
Itinerary
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Trip Levels
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.