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    5. Private Sunset Sailing in St. Augustine
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    Private Sunset Sailing in St. Augustine

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

    From$795

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    Discover what we've curated for you

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Private charter, Professional crew

    Highlights

    Set sail at sunset aboard a luxury yacht and take in St. Augustine's historic bayfront. Enjoy views of landmarks like the Castillo de San Marcos, the Bridge of Lions, the Great Cross, and the lighthouse with a professional crew.

    • Sail a luxury yacht along the bayfront
    • See Castillo de San Marcos and Bridge of Lions
    • Spot the Great Cross and St. Augustine Lighthouse
    • Relax with a professional crew on a private charter
    • Feel the sea breeze during a serene sunset
    • Purchase drinks and food onboard

    Things to know

    Maximum 6 guests per vessel. Arrive 15 minutes early. Wear non-marking shoes; no pets or smoking; avoid red wine and spray tanning.

    Cancellation Policy

    Cancel before 72 hours for a full refund. Cancel 71–25 hours before for a 50% refund; a $100 rescheduling fee applies. Cancel within 24 hours is non-refundable. Not applicable to cancellations due to dangerous weather conditions.

    Meeting details

    3076 Habor Drive, St Augustine, FL 32084

    Perfect for

    • Couples looking for a romantic St. Augustine getaway
    • Small groups celebrating special occasions together
    • History buffs wanting waterfront views of colonial landmarks
    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 #B3JN7W

    Private Charter - 35' Sailing Vessel

    $795

    Maximum of 6 people

    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

    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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