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    1. Local experiences/
    2. St. Augustine, FL/
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    4. Dinner Cruises/
    5. Sweetheart Head Over Heels Sailing Dinner Experience

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    Sweetheart Head Over Heels Sailing Dinner Experience

    Savor a private yacht dinner cruise with a chef-prepared meal and sparkling wine for a romantic escape.

    From$1,945

    Duration

    3 hours

    Ideal For

    Up to 10 people

    Includes

    Private yacht, dinner, sparkling wine

    Highlights

    Set sail on a private luxury yacht for a romantic evening with your special someone. Enjoy a 3-hour cruise along scenic waterways, complete with a chef-prepared five-course dinner and sparkling wine.

    1. Relax on a private yacht with stunning waterway views
    2. Indulge in a five-course dinner prepared by a private chef
    3. Toast with two bottles of house sparkling wine
    4. Enjoy quality time in a cozy, intimate setting
    5. Benefit from convenient and free marina parking

    What's Included

    1. Private yacht charter
    2. Five-course dinner
    3. Two bottles of sparkling wine

    Things to know

    All alcohol must be purchased in the office before departure. No red wines are available. Please wear non-marking shoes and avoid spray tanning products. Smoking and pets are not allowed on board.


    FAQs

    Q: How long is the sailing experience?

    A: The private charter lasts 3 hours along the Intracoastal Waterway and Matanzas Bay.


    Q: What is included in the dinner?

    A: A private chef prepares an upscale 5-course dinner with two bottles of house sparkling wine.


    Q: Can I bring my own alcohol?

    A: No. All alcohol must be purchased in the office before departure.


    Q: Is there a bathroom on board?

    A: Yes. The yacht has a private restroom available for guest use during the sail.


    Q: What should I wear?

    A: Wear shoes with non-marking soles such as deck or tennis shoes. Avoid high heels, hard soles, or black rubber soles.


    Q: Are blankets provided?

    A: Warm, cozy blankets for two are available for purchase at the office.


    Q: Where can I park?

    A: Free and convenient parking is available at the marina.

    Cancellation policy

    Deposit fully refundable up to 7 days prior to charter. 7 days prior, 50% of the charter 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 prior. If dangerous weather prevents departure, dinner will be served dockside.

    Meeting location

    3076 Harbor Drive St Augustine FL, 32084

    Perfect for

    • Couples celebrating anniversaries or planning romantic getaways
    • Groups of friends looking for an upscale night out on the water
    • Honeymooners wanting an intimate, gourmet dinner experience
    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 #69CKX8

    Private Charter - 41' Sailing Vessel

    $1,945

    Maximum of 8 people

    0

    Private Charter - 40' Sailing Catamaran

    $2,550

    Maximum of 10 people

    0

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    5.0 stars• 663 reviews

    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