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    1. Local experiences/
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    5. Cruise St. Augustine Bayfront on a Private 2-Hour Sail
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    Cruise St. Augustine Bayfront on a Private 2-Hour Sail

    Private 2-hour sail past St. Augustine’s historic bayfront sites

    5.0 stars• 740 reviews
    From$669incl. taxes and fees

    Duration

    2-hour

    Ideal For

    Up to 6 people

    Includes

    Private charter, USCG captain

    Highlights

    Sail from the dock and cruise the Tolomato and Matanzas Rivers toward St. Augustine’s historic bayfront. Relax on a private charter with a U.S. Coast Guard (USCG) licensed captain and keep an eye out for wildlife along the way.

    • Set sail on a private 2-hour charter
    • Cruise the Tolomato River and Matanzas River
    • View St. Augustine historic sites from the water
    • Look for dolphins near Porpoise Point
    • Park for free at the marina
    • Purchase food and beverages before departure

    Things to know

    Alcohol must be purchased in the office prior to departure; red wine is not available. Smoking, pets, and spray tanning products are not allowed onboard.

    Cancellation Policy

    Cancel before 72 hours: fully refundable. Cancel between 71–25 hours: 50% of charter full cost is non-refundable. Cancel within 24 hours: full cost is non-refundable. A $100 rescheduling fee applies between 71–25 hours. This does not apply to cancellation associated with dangerous weather conditions.

    FAQs

    Plan to arrive 15 minutes before departure to collect life jackets for children (if needed) and get provisions aboard.

    Guest capacity depends on the vessel you book. The experience description notes a maximum of 6 guests per vessel (not including captain and crew).

    Wear shoes with non-marking soles (deck shoes, tennis shoes, or white-soled shoes). Avoid hard soles, high heels, and black rubber-soled shoes.

    Meeting details

    3076 Habor Drive, St Augustine, FL 32084

    Experience provided by St Augustine Sailing
    Experience provided by St Augustine Sailing

    Perfect for

    • Couples seeking a romantic escape on the water
    • Friend groups looking for a unique group outing
    • Families wanting wildlife spotting and history

    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

    Report an issue

    Reference #FJQRT4

    Private Charter - 35' Sailing Vessel

    $669.38

    Maximum of 6 people

    0

    Private Charter - 38 Sailing Vessel

    $894.38

    Maximum of 8 people

    0

    Private Charter - 41' Sailing Vessel

    $1,006.88

    Maximum of 8 people

    0

    Private Charter - 40' Sailing Catamaran

    $1,119.38

    Maximum of 10 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
    740 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 5
    5/5

    Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.

    Photo of gerald bates

    gerald bates

    May 17, 2026

    Review 1 of 1
    5/5

    Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.

    Photo of gerald bates

    gerald bates

    May 17, 2026

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