Who we are

Maui Custom Charters is a small family-run business; we are a team of captains and crew who strive to exceed every one of your expectations. Whether it is sailing, snorkeling, whale watching, or enjoying the sunset, your charter will be an unforgettable experience. We are your captain, your crew, your concierge for the rest of your vacation, and hopefully someone to whom you can consider referring all of your family and friends.

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Get ready for an unforgettable day

A unique maui
experience

female crew setting sail on Maui sailboat

Private and Authentic

Maui is best enjoyed away from the crowds, on your own time, with top-notch personalized service. Our sailing operation is managed by born and raised locals, ensuring you receive an authentic and unforgettable experience. We strive to take you to less frequented reefs, cater sailing conditions to your comfort level, and provide as much comfort and relaxation, or heeled over adventure as you desire.

Genuine Boat Culture

Our boat culture is built upon treating all of our guests like our best friend’s best friends. This means your service with a smile is genuine. By the end of your private sailing trip we have most likely exchanged life stories, fascinating facts about Hawaii, laughs, tears, and vows to see each other again on the water or lands near and far.

Meet the Crew

Premier Location

Ma’alaea Harbor is conveniently located a short drive from the resort areas of Kihei and Wailea to the south, or Lahaina, Ka’anapali, Nāpili, Kahana, Kapalua to the west.

Gear Included

Maui Custom Charters provides all the gear for your snorkeling needs, entertaining, and having a great time out on the water. Whether you want to snorkel, watch the sunset, enjoy some cocktails, learn to sail, or just lay back and relax, we can customize the perfect trip to make your dreams come true.

FREQUENTLY ASKED QUESTIONS

Captain Anna talking to a guest on the sailboat

The fleet

S/V Artemis

S/V (Sailing Vessel) Artemis is a 47’ Leopard sailing catamaran equipped using the highest quality materials and top brand fittings. Leopard catamarans offer unparalleled standards in design and construction for reliability, seaworthiness, and performance.

Designed by world renowned Robertson and Caine, S/V Artemis’s sleek lines make her a dream to sail in any wind conditions presented to us in world-renowned Ma’alaea bay.
S/V Artemis’s interior is fully equipped with 4 private cabins, 4 marine heads, a spacious saloon, a fully equipped galley, and a bluetooth speaker system. Her exterior features a safe and comfortable cockpit area with the mainsheet traveler located overhead on the Targa arch. Fully shaded, the cockpit offers ample seating. The spacious swimming platform and sugar scoops are great for slipping into the water for snorkeling, or for cannonballs and jumping competitions.
The real star of the show is the bow of the vessel. The vast trampolines are perfect for relaxing and enjoying the spray and the sun while watching and listening to the blue ocean pass underneath you. Sit on one of our princess chairs, or lounge on the trampoline and enjoy everything Maui has to offer.

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S/V Nova

Charter-ready for sailing around the world-renowned waters of Maalaea, S/V Nova is a 42’ Catalina MKII, USA built and reputed as a leader in her class. By leading in design, cruising performance, and comfort, the Catalina 42 has become the choice of sailors worldwide.

The MKII version is the logical result of America’s most experienced sailboat builder continuing to listen carefully to the needs and desires of experienced sailors.
S/V Nova’s interior is fully equipped with 2 private cabins, 2 marine heads, a spacious saloon, a fully equipped galley, and a bluetooth speaker system. Her exterior features a spacious deck, shaded cockpit, dodgers, step down boarding platform with a fold-down swim ladder, and a hot freshwater shower.

F/V Marjorie Ann

FV Marjorie Ann is a 36’ Chesapeake Bay power boat built in Maryland in 2010 and driven across the country and shipped across the Pacific to Maui in 2012. She is an excellent vessel for afternoon whale watches, celebrations, ash scatterings, sunset charters, and more!

Marjorie Ann has a comfortable cabin, fully-shaded large back deck, large cooler with ice for all your beverages and snacks, an onboard marine head, and a great sound system. Most importantly she can accommodate up to 13 guests!

Your crew

Maui Custom Charters is one of the few companies on Maui owned and operated by born and raised captains. Our hand-selected and trained staff have been on island operating boats collectively for nearly 100 years, ensuring that your experience will be top notch.

Born and raised in Hana, Maui, Anna traveled to the east coast to attend Brown University and obtained a degree in marine science. She then returned home and has worked on the water since 2007 as crew and captain for power catamarans and as an underwater photographer for a humpback whale research group. Most of her time has been spent off the coast of Maui, but she has also worked in Washington, Florida, and the south Pacific. In her free time, Anna loves to cook, surf, dive, hunt, and spend time with her family and friends in Hana.

Originally from the east coast, Peter grew up in the Appalachian Mountains in western Maryland. He spent summers at the beach where he learned to sail. Moving to Maui after college in 2002, he led guided kayak tours for many years and became a PADI scuba instructor, but he never lost his love for boating. He began working on sailboats in 2010 and received his captain’s license in 2018. He has been sailing ever since! His other interests include playing music and fishing.

Kiera grew up traveling and has spent the majority of her life on the water. Her years have consisted of sailing, scuba diving, camping, wake boarding, paddle boarding, and jet boating. After graduating with her Bachelors degree she began to transform her passion into her career. She landed on Maui in 2015 and obtained her 50ton Captains License. Kiera loves conservation and dedicates her days to the preservation of our sea and land. When she isn’t on the boat she is up country working on an organic farm.

At 19, Kelly’s first command as captain was a 100’ triple engine charter boat. Born and raised in Haiku, Maui, Kelly has spent his entire career on the water captaining snorkel charters, whale watches, and fishing charters. He is Maui Custom Charter’s chief engineering manager. Kelly’s hobbies include fixing boats ;), hunting, fishing, and assisting with shark tagging projects. Cool fact: Kelly once rescued 5 scuba divers who had been swept out to sea from Molokini and lost for 5 hours.

Born and raised in Haiku, Maui, Monroe attended the University of Hawaii, Manoa and received a bachelor’s degree in biological sciences. He grew up working on boats in Ma’alaea harbor. He enjoys spending time with his wife and 3 young children, taking them surfing, sailing lessons, and fishing. Monroe is also Kelly’s older brother.

Captain Carrie moved to Maui 7 years ago from Minnesota and has been working on catamarans on the island ever since she arrived. Her love of marine wildlife and the year-round active lifestyle is what drew her to Maui. When not working on the water she loves to spend her free time hiking, spending time with friends, and traveling.

Tennasyn moved to Maui in 2022 to continue her career on the water and fulfill her lifelong dream of living in Hawaii. She moved here from St. Augustine, Florida, where she earned her Bachelor of Science in Coastal Environmental Science. With a passion for Marine Biology and all things ocean, her favorite activities include: sailing, free diving, fishing, and scuba diving. Originally hailing from Dallas, Texas, Tennasyn considers herself a true saltwater cowgirl.

First Mate Annie

Born and raised sailing the Great Lakes of Michigan, Annie came to Maui looking for warm weather and adventure. She has been working out of Ma’alaea Harbor since 2002 on a variety of snorkeling and fishing charters, as well as private motor yachts and sailboats. “One thing is for sure, I’ve been graciously appreciating the beauty and culture of this amazing place. Blessed and thankful!”