Charter-ready for sailing around the renowned waters of Maalaea, our sailing fleet provides the perfect choices for small private groups to escape the crowds. Join us for a gorgeous sunset sail, whale watch, enjoy some cocktails, learn to sail, celebrate a special occasion, or just lay back and relax. We can customize the perfect trip to make your dreams come true.
Posted By : 835tiffanyo
We had the BEST time with Kiera & Tennyson! They are wonderful captains, and took care of our every want/need! Absolutely a 🌟🌟🌟🌟🌟 review! Would do this again!! 100% recommended!
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Posted On : 2024-04-26 23:28:09 
Posted By : jmak5240
Amazing charter, so many great videos and photos. Crew was great, snacks and company were fantastic. Would definitely recommend this for a small family group!
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Posted On : 2024-04-17 23:14:23
Posted By : TANDTN
We did 2 sailings and both were magnificent. I would give 10 stars!!! Both trips were on S/V Nova. Our first was with Kiera and Annie. We saw SO many whales and the knowledge Kiera and Annie shared about the migration activity and the behavior was impressive. We had so much fun sailing and when we snorkeled we could hear them singing. Next we did the sunset with Peter and Tennasyn. Again, total knowledge of the whales...we saw so many breeches and the sunset was beautiful. The Nova is a beautiful sailing vessel. Both crews were so much fun and easy going which made our 40th anniversary all the more special. We even brought home some cool merch!
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Posted On : 2024-03-05 12:23:58
Posted By : Bdaviskc
Wonderful experience from start to finish! Captain Kiera and Tennyson were phenomenal hosts and we enjoyed every minute of our 3 hour whale watch/sunset cruise. The Nova is a great boat and very stable, snacks/charcut plate were awesome and it seemed like our drinks were always full. 150% recommend this group--we will be back! If you are considering booking with them--do it, you will not regret it!
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Posted On : 2024-03-04 12:14:50
Posted By : WineluvrMaui
Totally amazing trip with great crew and great Captain!!! Had such a great time on a private charter. Unbelievably good service! You'll be glad you booked with them.
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Posted On : 2024-01-24 21:00:30
Posted By : fuzzyc2024
Anna and Tennyson were the best! We had a great trip, and they were very kind, knowledgeable and overall made it a wonderful experience. Crew accommodated our unique timing experience so we could make our flight. Could not have had a better boating trip on Maui!!
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Posted On : 2024-01-13 21:02:38
Posted By : GlenLivet
My wife and I were treated (by our daughter and her husband) to a sunset sailing cruise for our 50th Anniversary. I cannot imagine it could have gone better. We left out of Ma'alaea Harbor north of Kihei. We were met by Captain Kiera and First Mate Tennasyn. Now, there are good sailors and there are truly good people. Kiera and Tennasyn were both. They were gracious, efficient and competent. All on board felt comfortable. We were blessed with ideal conditions, just enough wind to allow for sailing, but not to bounce us around. We sailed around Ma'alaea Bay for two hours during which time we had several encounters with Northern Humpback whales including some breeching whales and a mother and young one. It was exciting. As sunset approached, we were surrounded by the sounds of the waves lapping against the boat, the wind slapping the sails and the strains of Cousin IZ's "White Sandy Beach". It was magical. The final dip of the sun into the Pacific Ocean seemed almost anticlimactic. I cannot recommend Maui Custom Charters more highly. It was a highlight of our trip to Maui. Thank you Kiera and Tennasyn.
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Posted On : 2024-01-05 15:02:11
Posted By : howardb852
Love Maui! Our captain, Kiera, was fantastic! First of all, her knowledge of the boat and sailing in general is incredible. To say that she is a terrific captain would be an understatement. She made sure that everyone on the boat had fun, was safe at all times and got off the boat knowing a lot more about sailing, Hawaiian culture and marine habitats. We took a dedicated whale watching cruise a few days before our trip with Kiera. It was fun and we saw some whales but nowhere near as many as on our MC Charter cruise. She knew right where to go and how not to spook them.
This obviously maximized our viewing. I would recommend Maui Custom Charters and Captain Kiera to anyone thinking about this trip!
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Posted On : 2023-11-10 11:31:19
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