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    1. Local experiences/
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    5. Private Sunset Sailing Charter in St. Augustine
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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

    4.9 stars• 697 reviews
    From$1,861incl. taxes and fees

    Ideal For

    Up to 6 people

    Includes

    Private yacht, Dinner, Beverages

    Highlights

    Sail along the St. Augustine bayfront aboard a private luxury yacht as the sun sets. Enjoy a chef-prepared four-course dinner with wine, beer, or other beverages.

    • Relax aboard a private luxury sailing yacht
    • Savor a chef-prepared four-course dinner
    • Sip included wine, beer, or other beverages
    • Admire sunset views of the St. Augustine bayfront
    • Arrive 15 minutes early for boarding

    What's Included

    • Chef-prepared four-course dinner
    • Selection of wine, beer, or beverages

    Things to know

    Please make your dinner selection 2 weeks before your charter. Arrive 15 minutes prior to departure for check-in and boarding. Dress for the forecast; vessels provide weather protection.

    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$310per person
    Split with

    Cancellation Policy

    Deposit is fully refundable up to 7 days before the charter. From 7 days prior, a 50% non-refundable payment is due. At 72 hours, the remaining balance is charged and all payments are non-refundable. If weather prevents departure, dinner will be served dockside.

    Meeting details

    3076 Harbor Drive, St Augustine Florida 32084

    Perfect for

    • Couples celebrating anniversaries or engagements
    • Groups looking for a special night out in St. Augustine
    • Anyone seeking a romantic sunset experience with fine dining
    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

    Report an issue

    Reference #JTJ7PJ

    Dinner for 2 - Aboard 38' - Mon Cheri

    $1,861.88

    0

    Dinner for 4 - aboard 41' - Enchantee

    $2,255.62

    0

    Dinner for 6 - Aboard 40' - Wind Dancer

    $2,936.25

    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

    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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