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    1. Local experiences
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    5. /St Augustine Private Sailing for Up to 5 Guests
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    St Augustine Private Sailing for Up to 5 Guests

    Choose a morning or afternoon private sail for up to 5

    5.0 stars• 768 reviews

    Duration

    9AM - 1PM or 1PM - 5PM

    Ideal For

    Up to 5 people

    Highlights

    Set out on a half-day sailing session with morning or afternoon departure options. Enjoy a private day sail for up to five guests, subject to skipper requirements.

    • Choose a 9AM or 1PM departure
    • Complete a skipper checkout before departure
    • Submit a skipper resume prior to your sail
    • Sign a bareboat charter agreement and waiver
    • Add a captain to join if available

    Things to know

    Maximum of five persons onboard, including any added captain. Skipper checkout approval is at the Staff Captain's discretion. Funds are non-refundable if the skipper does not meet minimum skill requirements to operate unaccompanied.

    Split the cost with your group

    This booking is for the whole experience, which fits up to 5 guests.

    From$61per person
    Split with

    Cancellation Policy

    Cancel before 72 hours: fully refundable. Cancel between 71–25 hours: 50% of charter cost is non-refundable. Cancel within 24 hours: full cost is non-refundable. A rescheduling fee applies between 71–25 hours of charter. This does not apply to dangerous weather conditions.

    Product ID: WJQPXT

    Meeting details

    St Augustine Sailing, 3076 Harbor Dr, St. Augustine, FL 32084

    Experience provided by St Augustine Sailing

    Perfect for

    • Small groups looking for a sailing getaway
    • Experienced sailors ready for a half-day adventure
    • Friends seeking a unique coastal group activity

    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

    Private Day Sailor

    $309.38

    Fits up to 5 guests · 9AM - 1PM or 1PM - 5PM

    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
    768 reviews•Google Maps
    719
    13
    4
    2
    2

    St Augustine Sailing delivers exactly what you'd hope for in a maritime experience, with Dr. Dale and Captain Daniel earning particular praise for their expertise and warmth. Dr. Dale stands out as both a scientist and skilled instructor who runs everything from casual dolphin-watching tours to serious ASA certification courses. Reviewers consistently mention his teaching ability, patience (even calming someone through a panic attack during a maneuver), and deep knowledge of sailing mechanics. The Learn The Ropes courses seem especially popular, with multiple people mentioning how much they learned and feeling genuinely hooked on sailing afterward. Beyond the educational offerings, this outfit clearly knows how to create memorable outings. One couple raved about a wine and appetizer sail that included personalized touches like off-menu steaks, while families appreciated captains who let kids help raise sails and take the wheel. The boats themselves get compliments for their condition, and practical details like shade covers matter when you're out on Florida water. Wildlife sightings of dolphins and manatees add natural magic to the trips. Whether you want a romantic sunset cruise, a family adventure, or actual sailing instruction, the crew adapts well to different groups and consistently makes people feel welcomed rather than processed through a tourist experience.

    What people are saying

    Review 1 of 4
    5/5

    Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!

    Photo of Stephanie Weir

    Stephanie Weir

    August 13, 2026

    Review 1 of 1
    5/5

    Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!

    Photo of Stephanie Weir

    Stephanie Weir

    August 13, 2026

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