Sailing Packages

Sailing Hawaii -- Image of a luxurious Yacht from Above with woman swimming beside it.


Relax on white-sand beaches and swim in brilliant turquoise water, test your hand at sailing or just relax on the deck, wander through local culture, taste traditional Hawaiian food, hike to spectacular viewpoints & more.

A yacht adventure is the ideal way to experience what many consider the world’s most beautiful islands: the Hawaiian Islands. Sail for up to 15 days aboard our 15m (49 ft) yachts, with time for hiking, snorkelling, and relaxing. Explore ancient archaeological sites and tiki bar-lined harbours, dine on fresh seafood — don’t forget to try the Ahi Poke!


  • Sailing aboard a 15m (50 ft) sailing yacht (14 kts)
  • Fully licensed skipper
  • Snorkeling equipment
  • Basic items on the boat will be covered by a shared food pantry of about $100US per person.
  • 15m (50 ft) sailing yacht
  • Skipper/CEO throughout.
  • Small group experience; Max 8
  • 4 twin/double occupancy cabins, 3 shared bathrooms, 3 showers


Day 1 | Honolulu, Oahu

Arrival day. Join the group at 12:00 for a welcome meeting and safety briefing before beginning the sailing journey around the South Shore of Oahu. Enjoy a traditional Hawaiian night of fire and dancing under the stars at The Big Kahuna Luau.

Day 2 | West & Noth, Oahu

Get ready to sail to the West Side where we can find dolphins. There’s nothing like it, a magical experience beyond words. Jump right in and get up close with playful Spinner Dolphins in their home, the Pacific Ocean! Our experienced boat crew will lead you in to dolphin playgrounds, where you will explore an underwater world teeming with marine life. Sea turtles have been known to swim by, too! Sail to the North Shore and stop for lunch in Haleiwa Town.

Days 3–6 | Pearl Harbor & Circle Island, Oahu

Morning at Pearl Harbor, visiting the USS Arizona. In the afternoon, take a land tour around the Island of Oahu.

Day 7 | Lahaina, Maui

Celebrate the arrival on Maui by visiting the local towns and enjoying a cocktail on the beach. The valleys and waterfalls add adventure to the picturesque island.

Day 8 | Hana, Maui

Enjoy a free day in one of the most famous towns in Maui: Hana. Join the group at 17:00 to welcome some new friends before beginning the journey to Molokini.

Day 9 | Molokini Adventure

Once you reach Molokini Islet, the snorkel fun really begins. Enter the beautiful blue waters via the easy to use steps, or the fun and exciting waterslide! Keep your eyes peeled as there are over 250 species of fish that call this area home. View the beautiful fish, colorful reef, and perhaps even Hawaiian Green Sea Turtles during your time below the surface.

Days 10–13 | Molokai

Flexible itineraries give our experienced skippers the opportunity to showcase all the hidden gems you’re looking for, we follow the desires of the group and cater to the sailing experience to provide each group a quality journey while on board.

Day 14 | Lanai

Lanai is an island of intriguing contrasts. Hike the lunar landscape of Keahiakawelo (Garden of the Gods) or picnic overlooking Puu Pehe (Sweetheart Rock), named for a maiden Puu and her handsome warrior.

Day 15 | Honolulu

Depart at any time.

Call us at 808-690-9050 to arrange for your trip of a lifetime!

Couple jumping from a yacht into the water. Sea Turle diving deeper. Couple holding hands while snorkeling. Sailboat cruising through a channel. View of a sailboat cruising towards the sunset.