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Home / Activities / Maui’s Best Private Charter Sailing
Maui Activities Private Charter

Maui’s Best Private Charter Sailing

Experience Maui’s ocean your way with a private charter. Whether sailing, snorkeling, whale watching, or just watching the sunset, Maui Custom Charters delivers an experience that is truly memorable. An S/V Nova 42’ Catalina MKII is the perfect boat for small private groups to escape from the crowds.

Maui Private Sailing Charter Tour

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase through my links we may earn a commission at no additional cost to you. Read about our affiliate policies here.

Activity Overview

  • Departs From: Maui – Ma’alaea (Central)
  • Duration: 2 to 12 hours – you decide the length!
  • Included in the price: Private sailboat, captain, lunch or breakfast

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Whether you want to snorkel, watch the sunset, enjoy some cocktails, learn to sail, celebrate a special occasion, or just lay back and relax, then a private custom charter for up to 6 passengers will be perfect for your Maui vacation. Captain Anna and her crew at Maui Custom Charters can customize the perfect trip to make your dreams come true. 

Save 5% on your charter sail with promo code HVG5.

Click below to learn more and then call Captain Anna at 808-874-1110 to discuss your charter sail. Mention our code and she’ll take 5% off your charter. Thanks Captain Anna!

Book Online

Private Tour Highlights

Choose from five custom charter sailing experiences. But as the boat is yours, feel free to customize your experience. Want to learn how to sail, Captain Anna and the crew are excellent instructors! All tours are for up to 6 passengers.

  • Private Morning Snorkel Tour: 4 hours, snorkel where it is only accessible by boat
  • Private Afternoon Snorkel Tour: 4 hours, snorkel in a private, serene spot
  • Private Whale Watch Cruise: Jan-April during humpback whale season
  • Private Sunset Cruise: 2 hours
  • Private Custom Charter: 2 to 12 hours, the boat and day is yours

Our Experience

We’ve been lucky enough to go out twice with Captain Anna. Here’s a video of one of our sails.

About Maui Custom Charters

Maui Custom Charters is a small ʻohana run business. They are one of the few companies on Maui owned and operated by born and raised captains. Their hand-selected and trained staff have been on the island operating boats collectively for nearly 100 years, you can rest assured that your experience will be top-notch. Captain Anna also replies to Captain Anna from Hana (FYI).

They focus on providing genuine, thrilling, eco-friendly charters. Maui Custom Charter’s goal is to ensure you have the most incredible experience that you will look forward to having again, telling all your friends about, it and rebooking it every time you return to Maui. That is why The Hawaii Vacation Guide has gone out twice!

Remember: Save 5% on your charter sail with promo code HVG5.

Book online

We are affiliate partners with Maui Custom Charters which means we receive a small commission for each completed booking made through this site. This is done without any additional cost to you. You can read more about our affiliate policies here. Know that we only recommend tour operators that we know and trust. Your positive experience and your trust in us mean more than any affiliate commission. By booking tours through our website you help us to provide free information and videos to help you and other readers plan their perfect Hawaii vacation. Thank you so much for your support — you are amazing!

Aloha! We're Jordan and Erica.

We are Hawaii travelers who have lived on Maui and Oahu sharing our adventures, travel tips and resources, and honest reviews so you can easily plan your dream vacation to Hawaii.

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