Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Maalaea…
    3. /Water Activities
    4. /Sailing
    5. /Private Sailing Charter in Maalaea Bay
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Private Sailing Charter in Maalaea Bay

    Celebrate on a private catamaran with onboard appetizers and drinks

    5.0 stars• 163 reviews
    From$2,729incl. taxes and fees

    Duration

    2–12 hrs

    Ideal For

    Up to 6 people

    Includes

    Appetizers, nonalcoholic drinks

    Highlights

    Celebrate special occasions aboard S/V Artemis with a private sailing experience. Enjoy light appetizers and non-alcoholic drinks as you spend time on the water.

    • Celebrate weddings, proposals, birthdays, ash scatterings, or private dinners
    • Bring your own alcoholic beverages to enjoy onboard
    • Pack swimwear and towels for your time on the water
    • Bring a sweater or jacket for occasional water spray on deck
    • Expect gratuity separate from the listed price; private-yacht standard generally starts at 20%

    What's Included

    • Light appetizers
    • Deli lunch on charters of 4 hours or longer
    • Breakfast, depending on departure time
    • Water, juices, and sodas
    • Glassware for alcoholic beverages you bring

    Cancellation Policy

    Free cancellation with a full refund up to 48 hours before departure. No refund within 48 hours of departure. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    FAQs

    Enjoy light appetizers, water, juices, and sodas. Charters of 4 hours or longer include a deli lunch and, depending on your departure time, breakfast.

    Bring your own alcoholic beverages to enjoy onboard. Glassware is provided.

    Bring swimwear, towels, sunglasses, sunscreen, and a hat that you can secure in the wind. Bring a sweater or jacket for possible water spray on deck.

    Experience provided by Maui Custom Charters
    Experience provided by Maui Custom Charters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #SH9Z2U

    Two Hour Charter

    $2,729.09

    Seats 6 Passengers

    0

    Three Hour Charter

    $4,093.63

    Seats 6 passengers

    0

    Four Hour Charter

    $5,458.18

    Seats 6 Passengers

    0

    Five Hour Charter

    $6,822.72

    Seats 6 passengers

    0

    Six Hour Charter

    $8,187.26

    Seats 6 Passengers

    0

    Seven Hour Charter

    $9,551.81

    Seats 6 Passengers

    0

    Eight Hour Charter

    $10,916.35

    Seats 6 Passengers

    0

    Nine Hour Charter

    $12,280.90

    Seats 6 Passengers

    0

    Ten Hour Charter

    $13,645.44

    Seats 6 Passengers

    0

    Eleven Hour Charter

    $12,508.32

    Seats 6 Passengers

    0

    Twelve Hour Charter

    $15,009.98

    Seats 6 Passengers

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    163 reviews•Google Maps

    With a perfect track record across well over a hundred reviews, this charter operation consistently delivers exceptional private sailing experiences around Maui. The crew—particularly Captain Anna, JJ, Nessa, Tim, and Marcella—earn universal praise for being knowledgeable, personable, and genuinely attentive to their guests. They regularly spot whales, dolphins, and sea turtles during tours, and their expertise about marine life adds real depth to every outing. The boats themselves (a 42-foot Catalina and 47-foot Leopard catamaran) are described as immaculate, spacious, and comfortable. What stands out is how the crew adapts to different occasions. Guests have celebrated proposals, birthdays, and even memorial services, with the team handling each event thoughtfully and professionally. They're also skilled photographers who capture beautiful moments without being asked. Whether you're snorkeling, whale watching, or simply enjoying a sunset sail, the crew creates a relaxed atmosphere while prioritizing safety and comfort. Communication from booking through the trip itself is reportedly excellent, with weather updates and helpful planning support. This is clearly a top-tier choice for anyone wanting a memorable, personalized day on the water.

    Nearby activities

    Thumbnail
    Yacht ChartersUp to 6

    Snorkel & Sail Private Morning Charter in Maui

    From$6,822
    Thumbnail
    Private Fishing ChartersUp to 6

    Fishing & Snorkeling Charter in Ma'alaea Bay

    From$6,140
    Thumbnail
    Yacht ChartersUp to 6

    Full-Day Snorkel & Sail Catamaran Charter In Maui

    $9,551.81
    Thumbnail
    Yacht ChartersUp to 6

    Snorkel & Sail Full-Day Charter in Maalaea Bay

    $5,731.08
    Thumbnail
    Yacht ChartersUp to 6

    Sail on a Private Charter in Maalaea Bay

    From$1,637
    Thumbnail
    Yacht ChartersUp to 6

    Private Morning Snorkel & Sail Charter in Maui

    From$3,274