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    St Augustine Sailing

    St Augustine Sailing

    5.0 • 740 reviews
    St. Augustine, FL

    St. Augustine Sailing invites you to swap city streets for Atlantic breezes aboard an impeccably maintained fleet. For more than four decades, this family-run crew has transformed the nation’s oldest city into a playground of luxu...

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    Book St Augustine Sailing

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    Private Sunset Sailing in St. Augustine

    Sail a luxury yacht at sunset and see St. Augustine's historic bayfront

    $795
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    St Augustine Private Sailing for Up to 5 Guests

    Choose a morning or afternoon private sail for up to 5

    $309.38
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    St. Augustine Nights of Lights Sailing Tour

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

    $145.12person
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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

    From$669
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    Sunset Sailing Cruise in St Augustine

    Sail into sunset views of St Augustine landmarks on a small-group charter

    $201.38person
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    Sail on a Shared Day Charter in St Augustine

    Sail past St Augustine landmarks on a 2-hour small-group charter

    $167.62person
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    Sunset Dinner Cruise in St. Augustine

    Private sunset sail with a chef-prepared four-course dinner

    From$1,861
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    Sunset Sailing Charter in St Augustine

    Private 2-hour sunset sail for up to 6 in St. Augustine

    $894.38
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    Sip & Sail Sunset Cruise in St. Augustine

    Sail St. Augustine’s waterways with wine tasting or mimosas

    From$201person
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    Sail On A Brunch Cruise In St. Augustine

    Share a brunch sail with mimosas on a 35 ft monohull in St. Augustine

    $223.88person
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    Sail On a Private Brunch Cruise in St. Augustine

    Charter a luxury catamaran and enjoy a family-style brunch with bottomless mimosas

    $1,687.50
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    St. Augustine Sunset Cruise with Wine Pairings

    Savor expertly paired wines and seasonal appetizers as you sail past St. Augustine’s scenic coastline at sunset.

    $336.38person
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    Private Dinner Cruise on Yacht in St Augustine Note: This title prioritizes the distinctive activity (dinner cruise) over generic "yacht charter," uses the city name (St Augustine is a destination city), and maintains natural readability. "Yacht" is included for boat type specificity. The romantic "for Two" aspect is better suited for the description rather than the title, as it focuses on a narrow use case with lower search volume compared to the broader "dinner cruise" appeal.

    Savor a private yacht dinner cruise with a chef-prepared meal and sparkling wine for a romantic escape.

    $2,538.72
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    Sunset Sailing Charter in St Augustine

    Private 2-hour sunset sail past St. Augustine bayfront landmarks

    From$669

    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