We invite you to experience luxury world class sailing on our classic 60ft Columbia sailing yacht. As you know Maui offers some of the most pristine and breathtaking waters on the planet, and there’s no better way to experience it all than aboard your very own private charter on Island Star.

The next anchorage in your Island Paradise is always within sight and invariably as beautiful as the last. Whatever your desires, snorkeling, scuba, sailing Island Star will provide the vacation on a lifetime. The combination of gentle trade winds and pristine warm waters makes Maui the ideal place on earth to create a memorable charter adventure.

Where do you want to go? Just want a romantic sunset sail with your sweetheart? Or do you want to escape and adventure around all of the islands! Our experienced crew are eager to indulge your wishes and make it a memorable vacation. All of our trips involve snorkeling Maui’s exquisite reefs and searching for dolphins (and whales when in season). We encourage all our guests to get involved with the sailing aspect of our trips and allow everyone helm time if desired. Fishing lines are always out in hopes of catching a tuna, Mahi Mahi or even Ono, much to our crew’s delight; Scuba diving are also available with proper notice. We have a complete galley on board where we have the ability to prepare scrumptious lunches such as a hot BBQ, a gourmet deli-style lunch, or fresh island grilled fish.

All of our crew are current in First Aid and C.P.R. as well as being Coast Guard licensed captains.

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Trip: Dolphin Watch, Most Popular, Snorkeling, Whale Watching

Depart Ma‘alaea Harbor for Coral Gardens or Olowalu, or any one of our local favorite snorkel spots. After an hour of sailing aboard the Island Star, we’ll drop anchor near a beautiful reef, allowing for plenty of time to snorkel while your crew prepares your lunch.  Snorkel on pristine coral reefs with an abundance of tropical fish, a variety of colorful corals and the endangered Green Sea Turtles. After a hot lunch on deck, we set sail back to port.

We recommend this as a morning trip due to Tradewinds that tend to increase in the afternoons.

Set sail from Ma‘alaea Harbor on Maui for a full day of sailing, snorkeling, and fun in the sun aboard the Island Star. Anchor on the south side of the island in a remote, protected area. Snorkel on pristine coral reefs with an abundance of tropical fish, a variety of colorful corals and the endangered Green Sea Turtles.

During our sail, we will be in constant search for the ever playful Spinner Dolphins and Humpback Whales when they’re in season. The whales are seasonal visitors, arriving around the middle of December and remaining through the middle of May; if your trip occurs during these months, we will spend ample time observing these breathtaking giants.

The full day gives us the extra time to snorkel a second or third reef. After a full day of sailing, snorkeling, chef prepared lunch and sunbathing on deck, we’ll return to the marina just in time for sunset at sea.

Join us for two hours of sailing around Ma‘alaea Bay. Enjoy appetizers prepared by our onboard chef or catered by one of Maui’s finer restaurants while you sip on your favorite beverages. The full galley below decks enables onboard meal preparation. Extend your trip an hour to accommodate a delicious dinner served on the aft deck. After viewing Maui’s spectacular sunset at sea we return to port.

Island Star can cater to many different special events and our most popular a Maui Wedding and the Island Star makes for a perfect wedding site. We can provide you with wedding coordinators that we work with here on Maui, who can take care of all your needs. Our wedding sails are 3 hours. Arrangements can be made to HONEYMOON aboard the Island Star for your wedding night. The Island Star has a master stateroom featuring a deluxe king-size bed with an overhead light/hatch. Stereo speakers and a private shower and head, making it the ideal honeymoon suite.

Captain Nick

Captain Nicholas's Blecke grew up in Chicago, IL his passion for adventure began at a young age. Sailing in Lake Michigan is where it all started. Soon that passion lead him to the ocean, where he has sailed thousands of nautical miles crossing the pacific two times....

Captain Trent

Captain Trent Welsh was born and raised in Australia on the Sunshine Coast. Living close to the water he developed a passion for the ocean at a very young age. While growing up surfing and diving, he obtained his speed boat license which led him Nth to the Great...

Captain Timothy

Originally hailing from the North Fork of Long Island, I arrived in Hawaii the second time around in 2001 to work on learning about and protecting marine mammals and coral reefs in the Hawaiian Islands working with non profit organizations.  Eventually I discovered...

1st Mate Ryan

With an M.A. in Human Ecology and teaching degree from the University of Hawaii, Ryan is also a licensed 50 ton USCG captain. He has been certified as an EMT, licensed as a Realtor, credentialed as a secondary education teacher, certified as a Maui County life guard,...

Captain Bryan Stewart

Captain and crew on more than a dozen charter boats on Maui since 1987. 25 years as a licensed captain. Operating Sailboats, dive, snorkel, and whale watching trips. Divemaster, videographer, sailing instructor, fisherman, and sometimes tour guide. North shore...

Captain Jonathan Bader

Jonathan Bader grew up in Atlanta, Georgia. After high school he started as a landscaper at Post Properties luxury apartment homes. After 3 years he was promoted within the company to utility sub metering technician. In December 2008 Jonathan was laid off from Post...

First Mate Ian

Ian Nelson was born and raised in California. He attended college in San Luis Obispo California and moved to Maui in 2007 to pursue his passion for ocean sports. Since moving to Hawaii, Ian spent the last ten years learning and working in the boating industry. When he...

Captain Bryan Barr

Originally from Seattle, I found my way up north to Alaska to work aboard tour vessels for whale watching and glacier tours. It's up there that I found a passion for the water and the wildlife and sites in and around it. After years up in Alaska and Seattle, and...

Our Location

Click on the red pin for our address and more info. Click here for driving directions

Island Star Sailing

Island Star Sailing Excursions

Slip #42 Ma’alaea Harbor

Wailuku, HI  96793

(808) 669-7827

– Click here for driving directions

Hawaii Ocean Rafting

Shooting Star Scarab