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    1. Local experiences
    2. /Things to do in St. Augustine…
    3. /Dining Experiences
    4. /Dinner Cruises
    5. /Sunset Dinner Cruise in St. Augustine
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    Sunset Dinner Cruise in St. Augustine

    Private yacht dining with sunset views of St. Augustine

    5.0 stars• 768 reviews

    Duration

    3 hrs

    Ideal For

    Up to 6 people

    Includes

    4-course meal, beverages

    Highlights

    Sail St. Augustine's bayfront at sunset aboard a private luxury yacht while enjoying a chef-prepared four-course dinner. Take in waterfront scenery, historic skyline views, and an intimate evening on the water.

    • Explore the bayfront and river aboard a private luxury sailing yacht
    • Take in views of the historic skyline, waterfront homes, and Bridge of Lions
    • Savor each course as it is served during your sail
    • Watch for dolphins and other marine wildlife along the route

    Itinerary

    #Day of Your Sail

    ✅ Arrive & Check-In – Please check in 15-20 minutes before departure.

    ✅ Final Weather Check – Be aware of any last-minute weather updates.

    ✅ Transportation Coordination – Ensure timely arrival for check-in to avoid missing your departure.

    #Dinner Cruise Experience

    🍽 Personalized Dining – Guests will be guided to their tables upon boarding.

    🥂 Welcome Beverage – Enjoy your first drink of choice once the safety briefing is complete and the vessel departs.

    🌊 Scenic Dining – Relax as each course is served while sailing along the bayfront and river. Dessert is typically enjoyed on the return trip.

    🐬 Spot Marine Life – Keep an eye out for dolphins and other marine wildlife during your voyage!

    #Post-Sail Departure

    ✅ Wrap-Up & Docking – Gather your belongings and ask the crew any sailing-related questions.

    📸 Share Your Experience! Tag @StAugustineSailing on social media and leave a review to share your adventure with others!

    We look forward to welcoming you aboard for an unforgettable sailing experience!

    What's Included

    • Chef-prepared four-course dinner
    • Wine, beer, or other beverages

    Important details

    • Complete the required waiver before sailing
    • Submit your dinner selection at least 2 weeks before your charter
    • Wear comfortable, non-marking, non-slip shoes; heels and black-soled shoes are not permitted

    Cancellation Policy

    Cancel at least 7 days before charter for a full deposit refund. Within 7 days, 50% of the charter cost is due and nonrefundable. Within 72 hours, all payments are nonrefundable. If dangerous weather prevents departure, dinner is served dockside.

    Product ID: JTJ7PJ

    FAQs

    Dress for the forecasted weather. Wear smart casual clothing and consider bringing a light jacket or sweater since it can get breezy on the water.

    Wear comfortable, non-marking, non-slip shoes. Avoid heels or black-soled shoes, since they can scuff the deck.

    Yes. Each vessel has a head (bathroom).

    Meeting details

    St. Augustine Sailing, 3076 Harbor Dr, St. Augustine, FL 32084

    Experience provided by St Augustine Sailing

    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

    Related locations

    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 1-877-GREET-WELL

    Report an issue

    Dinner for 2 - Aboard 38'

    $2,166.21

    0

    Dinner for 4 - Aboard 41'

    $2,626.73

    0

    Dinner for 6 - Aboard 40'

    $3,422.79

    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

    5.0
    Excellent
    768 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 4
    5/5

    Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!

    Photo of Stephanie Weir

    Stephanie Weir

    August 13, 2026

    Review 1 of 1
    5/5

    Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!

    Photo of Stephanie Weir

    Stephanie Weir

    August 13, 2026

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