SAILING

Maui - Sailing

Maui sailing trips offer an extraordinary way to explore the island's beautiful waters and coastline. Here's what you can expect from a Maui sailing charter: Ideal Sailing Conditions: The strong trade winds, particularly in late morning and afternoon, create perfect See more...

Top Review Scores Listed First

Barefoot Hawaii may earn a commission when you book through links on this page.

Maui Custom Charters

Maui Custom Charters in Hawaiʻi

Maui Custom Charters specializes in private sailing excursions, offering tailored experiences that let guests explore Maui's coastline with elegance and ease. Whether seeking a serene sunset sail, a lovely day of snorkeling, or a custom adventure, their expertly crewed sails provide an unforgettable way to experience the island's beauty.

Catamaran Private Morning Snorkel And Sail in Maui
Lowest Price Guarantee
All Fees and Taxes Included
Full Day Private Catamaran Sailing and Snorkeling Charter
Lowest Price Guarantee
All Fees and Taxes Included

Gungho Sailing Private Snorkel Sail

Gungho Sailing Private Snorkel Sail in Hawaiʻi

Gungho Sailing offers a private snorkel sail that promises a personalized and exclusive sea adventure. Aboard a classic sailing yacht, guests explore Maui’s vibrant marine ecosystems, snorkeling in secluded spots teeming with aquatic life. The experience combines the tranquility of sailing with the thrill of underwater discovery, enhanced by attentive, bespoke service.

Alii Nui Sailing

Alii Nui Sailing in Hawaiʻi

Alii Nui Sailing Charters offers a premier sailing experience, showcasing Maui's beauty from the sea. Their luxurious catamaran and dedicated crew provide a top-tier experience with snorkeling, dining, and sunset sails, ensuring every moment is filled with elegance and unforgettable marine encounters.

Kainani Sailing Charters

Kainani Sailing Charters in Hawaiʻi

Kainani Sailing Charters specializes in intimate, personalized voyages along Maui’s scenic coast. Their commitment to exclusivity and attention to detail ensures a unique experience, with opportunities for snorkeling, sunset viewing, and whale watching, all while sailing aboard a luxurious, well-appointed vessel.

Sea Maui

Sea Maui in Hawaiʻi

Sea Maui excels in sailing with a fleet of high-performance catamarans designed for both comfort and speed. Their expert crews navigate Maui’s waters with skill, offering guests exhilarating sails to stunning snorkeling spots and picturesque sunset views, making every journey on the water an unforgettable sailing adventure.

Gemini Sailing Charters

Gemini Sailing Charters in Hawaiʻi

Gemini Sailing Charters delivers an exceptional sailing experience off Maui's west coast shores. Aboard their spacious catamaran, guests enjoy breathtaking views, crystal-clear snorkeling waters, and a friendly crew. The relaxed ambiance is perfect for sunbathing, sightseeing, and making lasting memories on the Pacific.

Sail Maui

Sail Maui in Hawaiʻi

Sail Maui is renowned for its exceptional sailing excursions, featuring state-of-the-art catamarans that glide effortlessly across the Pacific. Their expertly guided tours offer unparalleled opportunities to explore Maui’s scenic coastlines and vibrant marine environments, providing both thrilling adventures and serene sunset sails.

West Maui Snorkel & Sail from Ma'alaea Harbor
Lowest Price Guarantee
All Fees and Taxes Included
Molokini Snorkel and Performance Sail from Ma'alaea Harbor
Lowest Price Guarantee
All Fees and Taxes Included

Kai Kanani Sail and Snorkel

Kai Kanani Sail and Snorkel in Hawaiʻi

The Kai Kanani Signature Deluxe Snorkel to Molokini offers a unique experience due to its exclusive South Maui location, which allows for snorkeling at Molokini Crater with minimal crowds. The tour includes two snorkeling locations, highlighting the vibrant marine life and coral reefs, and provides a chance to swim with Hawaiian Green Sea Turtles. Guests enjoy a gourmet lunch and open bar, along with shuttle service from Wailea Resorts, making it a luxurious and convenient way to explore the underwater beauty of Molokini.

Hula Girl

Hula Girl in Hawaiʻi

Hula Girl Sailing Charters offers luxurious and customizable sailing experiences along Maui's stunning coastline. With state-of-the-art vessels and tailored itineraries, guests enjoy gourmet dining, exceptional service, and opportunities for sailing, snorkeling, whale watching, or simply relaxing on deck, making each voyage uniquely memorable.

Maui Sailing Canoe

Maui Sailing Canoe in Hawaiʻi

Maui Sailing Canoe offers a unique, culturally immersive experience on traditional Hawaiian sailing canoes. Blending adventure with heritage, guests learn about Polynesian navigation and the rich history of the islands while gliding across Maui’s turquoise waters. This hands-on journey not only provides an opportunity for spectacular snorkeling and wildlife encounters but also deepens the connection to Hawaii's ancestral maritime traditions.

Hawaiian Canoe Sailing Experience in Maui
Lowest Price Guarantee
All Fees and Taxes Included

Pacific Whale Foundation

Pacific Whale Foundation in Hawaiʻi

The Pacific Whale Foundation offers a variety of sailing adventures that combine marine research and environmental education. Their sailing trips focus on conservation and offer guests a unique opportunity to learn about marine ecosystems while enjoying the natural beauty of Maui’s oceanic surroundings aboard eco-friendly sailing vessels.

Whale Watch Sail Deluxe Tour from Maalaea
Lowest Price Guarantee
All Fees and Taxes Included

Maui Sailing

Maui sailing trips offer an extraordinary way to explore the island's beautiful waters and coastline. Here's what you can expect from a Maui sailing charter:

  • Ideal Sailing Conditions: The strong trade winds, particularly in late morning and afternoon, create perfect conditions for sailing.
  • Sailing Destinations: Popular destinations include Molokini, where mornings offer calm waters and afternoons bring fun winds for the return.
  • Routes: Sail along West and South Maui, stopping at secluded beaches and scenic cliffs. Some trips include snorkeling or light-line fishing.
  • Seasonal Factors: Trade winds prevail around 300 days a year, primarily affecting the north and eastern shores in spring, summer, and fall. Popular departure points include Kaanapali and Maalaea, with stronger winds in the late morning and afternoon.

Whether you’re looking for a relaxing sail or an adventurous journey, Maui sailing charters offer an exciting way to enjoy the island's beauty.

Back To Top
Kauai Oahu Maui Big Island

Disclaimer

Independence:

We do not operate or endorse any specific activities.

Lowest Price Guarantee:

This is supported by Viator.

Vendor Representation:

We aim to represent a broad range of vendors. Vendors must have an operational website and online reviews to be included in our directory.

Website Functionality:

We exclude vendors whose websites are not functioning properly.

Liability:

We are not responsible for any website malfunctions or potential malware associated with the listed websites, all of which can be found on the internet. Similarly, we are not liable for any accidents, misinformation, fatalities, or any other unfortunate events that may occur during any tour, from the ticketing process to the tour itself and even after the tour is completed. We have no involvement in the actual operation of the hundreds of tours listed on this site. Our sole intention is to provide listings of available tours along with their official websites and reviews from professional sources, enabling you to use this information, along with any other resources you find, to make informed decisions about which tours to participate in.

Benefits of Using Our Lowest Price Guarantee Button

Lowest Price Guarantee:

Viator offers transparent pricing with no hidden fees or last-minute markups. If you find a lower price elsewhere, Viator will refund the difference promptly.

The Price You See Is What You Get

When you see the price on a Lowest Price Guarantee page that will be the full price including all taxes and fees. When you compare this with other websites you will often see an original price but additional taxes and fees will be added when you move to checkout.

Real-Time Booking:

Confirm your booking instantly without waiting, allowing you to finalize other vacation plans immediately.

Flexible Payment Options:

Reserve a tour now and pay later, usually within two to three days of the tour. Viator will send you a reminder email a day before the payment is due.

Easy Cancellation:

Get a full refund if you cancel before 24 hours of the tour time. Some specific tours may have a longer cancellation period, clearly stated on your voucher.

Dispute Resolution:

Viator will intervene on your behalf to resolve disputes with activity companies booked through one of their pages.

24/7 Support:

Access support anytime through chat and email.

Convenience:

Book multiple activities through Viator for a streamlined process, avoiding different policies and procedures of individual tour companies.

Quick Refunds:

Receive refunds quickly, usually within two days, unlike the typically slower individual activity bookkeeping departments.

Direct Communication:

Use Viator's online chat feature to communicate directly with tour operators for special requests or inquiries.