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    5. St Augustine Sunset Sailing Charter
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    St Augustine Sunset Sailing Charter

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

    From$201/ personincl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 12 people

    Includes

    Captain & crew, Free parking

    Highlights

    Make it a night to remember on a 2 hour small group sunset sail in St Augustine. Feel the ocean breeze as you pass landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse with a professional crew.

    • Sail along the historic waterfront at sunset
    • See Castillo de San Marco, Bridge of Lions, and the Lighthouse
    • Relax while the professional crew handles the vessel
    • Park conveniently with free marina parking
    • Purchase food and beverages on site
    • Arrive 10 minutes early for boarding

    What's Included

    • Captain and crew
    • Sailing vessel
    • Free marina parking

    Things to know

    A minimum of 2 guests is required to depart; maximum 12 guests. Wear non-marking shoes and avoid hard soles, high heels, and black rubber soles. No pets or smoking on board; alcohol must be purchased in the office before departure.

    Cancellation Policy

    Cancel 72+ hours before for a full refund of your deposit. Cancel 71–25 hours prior: 50% of the charter cost is non refundable. Cancel within 24 hours: full charter cost is non refundable. Rescheduling 71–25 hours prior incurs a $100 fee. Weather-related cancellations for dangerous conditions are excluded.

    Meeting details

    3076 Habor Drive, St Augustine, FL 32084

    Perfect for

    • Couples seeking a romantic evening with historic views
    • Small groups wanting a relaxed waterfront experience
    • History buffs touring St Augustine's 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 #DRG5V2

    Person

    $201.38

    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

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