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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

    From$309incl. taxes and fees

    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.

    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.

    Meeting details

    3076 Harbor Dr,, St. Augustine, FL, 32084-2123

    Perfect for

    • Small groups looking for a sailing getaway
    • Experienced sailors ready for a half-day adventure
    • Friends seeking a unique coastal group activity
    Experience provided by St Augustine Sailing
    Experience provided by St Augustine Sailing

    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 (650) 414-7338

    Reference #WJQPXT

    Private Day Sailor

    $309.38

    Max - up to 5

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    4.9 stars• 697 reviews

    Review summary

    4.9
    Excellent
    697 reviews•Google Maps

    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

    Great day with the Crew! Kevin is an amazing captain and we learned quite a bit from him. Highly recommend him for people wanting to improve their sailing skills.

    Photo of Rosser Pace

    Rosser Pace

    March 30, 2026

    Review 1 of 1
    5/5

    Great day with the Crew! Kevin is an amazing captain and we learned quite a bit from him. Highly recommend him for people wanting to improve their sailing skills.

    Photo of Rosser Pace

    Rosser Pace

    March 30, 2026

    Great for groups

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