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    St Augustine Sailing

    St Augustine Sailing

    4.9 • 697 reviews
    St. Augustine, FL

    St. Augustine Sailing invites you to trade city streets for ocean breeze aboard their impeccably maintained luxury yachts. Led by an enthusiastic crew of Coast Guard-licensed captains and hospitality pros, each charter is crafted ...

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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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    St. Augustine Private Sailing Charter & Harbor Tour

    Sail a private 2-hour charter past St. Augustine's historic waterfront with USCG-licensed captains

    From$669
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    St Augustine Sunset Sailing Charter

    Sail at sunset past St Augustine landmarks with a small group and professional crew

    $201.38person
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    Small Group Sailing: Historic St. Augustine Bay

    Sail past historic St. Augustine landmarks with a friendly crew

    $167.62person
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    Private Sunset Sailing Charter in St. Augustine

    Savor a chef-prepared four-course meal with drinks aboard a private luxury yacht at sunset

    From$1,861
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    Private Crewed Sail Through St. Augustine Bay

    See St Augustine landmarks on a private crewed sail

    $894.38
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    St. Augustine Sailing with Wine & Mimosas

    Savor mimosas or seasonal wines while sailing St. Augustine’s scenic waterways with a captain

    From$201person
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    Sailing & Brunch Cruise in St. Augustine

    Savor mimosas and a boxed brunch while sailing St. Augustine with a captain and crew

    $223.88person
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    St. Augustine Private Catamaran Brunch Cruise

    Savor family-style brunch and bottomless mimosas on a private catamaran with views of St. Augustine

    $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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    Private Sunset Sailing Charter in St Augustine

    Experience a luxury sunset sail with stunning views of St Augustine’s historic landmarks.

    From$669

    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