Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Lahaina…
    3. /Water Activities
    4. /Sailing
    5. /Private 4-Hour Sailing Lesson in Lahaina
    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
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Private 4-Hour Sailing Lesson in Lahaina

    Build sailing skills with instruction tailored to your experience

    5.0 stars• 124 reviews
    From$2,729incl. taxes and fees

    Duration

    4 hrs

    Ideal For

    Up to 4 people

    Includes

    Water, sparkling water, juice

    Highlights

    Set sail for hands-on instruction tailored to your experience, whether you are new to sailing or building on existing skills. Bring your own alcohol or extra food to store in the onboard cooler.
    • Learn sailing skills at a pace tailored to your experience
    • Build on existing knowledge or start with beginner instruction
    • Bring reef-safe, non-spray sunscreen, a hat, and sunglasses
    • Pack a swimsuit and towel if you plan to swim

    What's Included

    • Lunch
    • Water
    • Sparkling water
    • Juice

    Know before you go

    • Arrive 5 minutes before departure
    • Sign a paper waiver upon arrival
    • Leave drugs at home; smoking and vaping are prohibited aboard

    Cancellation Policy

    Rebook or receive a full refund with at least 72 hours' notice. Full refund if the operator cancels due to weather. No-shows are charged the full price.

    FAQs

    Gratuity is welcomed for the crew. A 15–25% gratuity is typical for private boat charters.

    Meeting details

    Lahaina Harbor, Maui

    Experience provided by Gungho Sailing
    Experience provided by Gungho Sailing

    Related locations

    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 #V5FTNV

    Private Lesson

    $2,729.09

    Up to 4 People

    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
    124 reviews•Google Maps
    119
    0
    0
    0
    0

    Ali and Keahi are the heart of this operation, a couple whose genuine love of sailing and deep connection to Maui comes through in every review. Guests consistently rave about how personable and knowledgeable they are, turning what could be a standard boat tour into something that feels personal and memorable. Wildlife sightings, particularly whales, come up constantly, though reviewers are refreshingly honest that nature does its own thing out there. The private charter format is a real differentiator here. Families with young kids, couples celebrating milestones, first-time sailors, repeat visitors over multiple years, the common thread is that people feel genuinely cared for rather than herded through a tourist experience. Ali's habit of sharing local dining and activity recommendations has even earned its own shoutout in more than one review. Across the board, these are some of the most enthusiastic reviews you'll see for any Maui activity. The consistent five-star rating over a large number of reviews is hard to argue with. If you're on the fence, the flexibility and communication Ali and Keahi brought during a stretch of stormy weather says a lot about how they operate when things get complicated.

    What people are saying

    Review 1 of 4
    5/5

    Amazing experience. The captain and Allie were very attentive and helpful. Loved the snorkeling. I highly recommend Gung-ho sailing if you want to avoid the large snorkeling tours.

    Photo of Nadia Yakoob

    Nadia Yakoob

    July 7, 2026

    Review 1 of 1
    5/5

    Amazing experience. The captain and Allie were very attentive and helpful. Loved the snorkeling. I highly recommend Gung-ho sailing if you want to avoid the large snorkeling tours.

    Photo of Nadia Yakoob

    Nadia Yakoob

    July 7, 2026

    Nearby activities

    Thumbnail
    SnorkelingUp to 6

    Private Snorkel & Sail Charter in Maui

    $2,160.53
    Thumbnail
    SailingUp to 6

    Lahaina 3-Hour Private Day Sail

    From$1,080
    Thumbnail
    SailingUp to 6

    Private Sunset Sail in Maui

    $1,620.40
    Thumbnail
    Scuba Diving

    Beginner Scuba Diving Lesson in Kaanapali

    From$163/ person
    Thumbnail
    Scuba Diving

    Private 2-Hour Shore Dive in Kaanapali

    From$780
    Thumbnail
    Scuba DivingUp to 4

    Shark, Turtle & Wreck Dive in Lahaina

    From$815