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    5. St. Augustine Sunset Cruise with Wine Pairings
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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.

    5.0 stars• 663 reviews
    $299/ person

    Duration

    2 - Hours

    Includes

    Luxury yacht, wine tasting, appetizers

    Highlights

    Experience a luxurious evening on the water with a 2-hour sunset cruise featuring gourmet cuisine and fine wines. Relax as a sommelier guides you through a curated tasting while you enjoy breathtaking views of St. Augustine’s historic coastline.

    1. Set sail aboard a luxury yacht for a sunset cruise
    2. Savor a flight of wines paired by a sommelier
    3. Enjoy seasonally inspired gourmet appetizers
    4. Relax with attentive, high-end service throughout
    5. Take in stunning views of the St. Augustine coastline

    What's Included

    1. 2-hour sunset cruise on a luxury sailing yacht
    2. Captain, chef, and sommelier-guided wine tasting
    3. Seasonal appetizers paired with select wines

    Cancellation Policy

    Deposit fully refundable up to 7 days prior to charter. 7 days prior, 50% of the cost is due and becomes non-refundable. 72 hours prior, the remaining balance is charged and all payments are non-refundable. Chef and food costs are non-refundable at 72 hours. If dangerous weather prevents departure, the tasting will be served dockside or in a private room onsite.

    FAQs

    Yes, free parking is available in the marina.

    This experience is best suited for adults due to the wine pairing

    Yes, dietary preferences or allergies can often be accommodated with advance notice at the time of booking.

    Meeting details

    3076 Harbor Drive, St Augustine Florida 32084

    Perfect for

    • Wine-loving couples seeking a romantic St. Augustine evening
    • Friend groups celebrating a special occasion on the water
    • Adults looking for upscale coastal dining with sommelier guidance
    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 #QNPSEH

    $299 / person

    0

    Why book through Greetwell?

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      Most experiences can be cancelled for a full refund

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    Review summary

    5.0
    Excellent
    663 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 5
    5/5

    Where to begin?! So many great things to say about this experience, the company and the captain! Truly from beginning to end I was impressed with the warmth and professionalism of the team at St. Augustine Sailing. I visit St. Augustine once a year for a spa + boating getaway and when I came across SAS I was thrilled to find they offered a sailing option with brunch in addition to so many other wonderful options. I called to ask a couple questions and the customer service etiquette and the friendly smiles of the staff, Lauren & Dirk, on to the day of my outing were excellent. Owner, Roseanne, was also delightfully to speak with and has done an amazing job with leading her team and attention to details. I had Kevin as my Captain and when I say he took the day trip to the next level of expertise, comfort and enjoyment for my time out on the water - he did not disappoint. He was kind, friendly, engaging and super knowledgeable. He was informative of the area as we sailed and gave good local recommendations for the rest of my stay. Hands down SAS is the areas BEST yacht and sail boating company offering a more private and exclusive experience away from the hustle and bustle of the overcrowded tourist boats. The added luxury of their gorgeous fleet is well worth the cost which was also very affordable for the over the top experience they offer. I love to travel and am always looking for a personalized experience and this was it! I’ll be back and I’m bringing friends. I’ve found my go to when visiting St, Augustine!

    Photo of Takiya La'Shaune

    Takiya La'Shaune

    July 19, 2025

    Review 1 of 1
    5/5

    Where to begin?! So many great things to say about this experience, the company and the captain! Truly from beginning to end I was impressed with the warmth and professionalism of the team at St. Augustine Sailing. I visit St. Augustine once a year for a spa + boating getaway and when I came across SAS I was thrilled to find they offered a sailing option with brunch in addition to so many other wonderful options. I called to ask a couple questions and the customer service etiquette and the friendly smiles of the staff, Lauren & Dirk, on to the day of my outing were excellent. Owner, Roseanne, was also delightfully to speak with and has done an amazing job with leading her team and attention to details. I had Kevin as my Captain and when I say he took the day trip to the next level of expertise, comfort and enjoyment for my time out on the water - he did not disappoint. He was kind, friendly, engaging and super knowledgeable. He was informative of the area as we sailed and gave good local recommendations for the rest of my stay. Hands down SAS is the areas BEST yacht and sail boating company offering a more private and exclusive experience away from the hustle and bustle of the overcrowded tourist boats. The added luxury of their gorgeous fleet is well worth the cost which was also very affordable for the over the top experience they offer. I love to travel and am always looking for a personalized experience and this was it! I’ll be back and I’m bringing friends. I’ve found my go to when visiting St, Augustine!

    Photo of Takiya La'Shaune

    Takiya La'Shaune

    July 19, 2025

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