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    1. Local experiences/
    2. St. Augustine, FL/
    3. Water Activities/
    4. Sailing/
    5. Shared Day Sailing Charter in St. Augustine

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
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    Shared Day Sailing Charter in St. Augustine

    Sail past historic St. Augustine landmarks with a friendly crew

    From$129/ person

    Duration

    2 hrs

    Includes

    Sailing, Professional crew, Parking

    Highlights

    Sail St. Augustine on a cozy 2 hour small group charter. Take in views of the Castillo de San Marco, the Bridge of Lions, and the lighthouse with an experienced crew.

    • See iconic landmarks from the water
    • Relax aboard a comfortable sailboat
    • Benefit from a professional crew
    • Park free at the marina
    • Purchase drinks and snacks on site
    • Arrive early for check-in

    What's Included

    • Sailing experience
    • Professional crew
    • Free marina parking

    Things to know

    Wear non-marking sole shoes; avoid hard soles and high heels. Alcohol must be purchased on site; no red wine. No smoking, pets, or spray tanning products on board.

    Cancellation policy

    Cancel before 72 hours: fully refundable. Cancel between 71 and 25 hours: 50% of charter cost is nonrefundable. Cancel within 24 hours: full cost is nonrefundable. A $100 rescheduling fee applies between 71 and 25 hours. Does not apply to cancellations due to dangerous weather.

    Meeting location

    3076 Habor Drive, St Augustine, FL 32084

    Perfect for

    • Couples seeking a romantic afternoon on the water
    • Small groups wanting historic views without crowds
    • First-time sailors looking for a guided introduction
    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 #AX6U4C

    Person

    $129

    1

    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