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    1. Local experiences/
    2. St. Augustine, FL/
    3. Water Activities/
    4. Sailing/
    5. Private Day Sail on St. Augustine's Historic Bayfront

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
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    Private Day Sail on St. Augustine's Historic Bayfront

    Sail a private 2-hour charter past St. Augustine's historic waterfront with USCG-licensed captains

    From$595

    Duration

    2 hrs

    Includes

    Private charter, USCG captain

    Highlights

    Slip away from the dock and sail the Tolomato and Matanzas Rivers to St. Augustine's historic bayfront. Look for wildlife and enjoy city views on your private 2-hour charter with a professional USCG-licensed captain.

    • Explore the Tolomato and Matanzas Rivers
    • Spot dolphins near Porpoise Point
    • View St. Augustine's historic bayfront
    • Relax aboard a luxury sailing vessel
    • Bring friends, family, or a special someone
    • Purchase food and beverages before departure

    Things to know

    Alcohol must be purchased in the office before departure; no red wine. Wear non-marking shoes and avoid high heels or black soles. No pets or smoking on board, and no spray tanning products; free marina parking available.

    Cancellation policy

    Cancel 72+ hours before departure for a full refund. Cancel 25-71 hours prior and 50% is nonrefundable; rescheduling then incurs a $100 fee. Cancel within 24 hours and the full cost is nonrefundable. Dangerous weather exceptions apply.

    Meeting location

    3076 Habor Drive, St Augustine, FL 32084

    Perfect for

    • Couples seeking a romantic escape on the water
    • Friend groups looking for a unique group outing
    • Families wanting wildlife spotting and history
    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 #FJQRT4

    Private Charter - 35' Sailing Vessel

    $595

    Maximum of 6 people

    0

    Private Charter - 38 Sailing Vessel

    $695

    Maximum of 8 people

    0

    Private Charter - 41' Sailing Vessel

    $795

    Maximum of 8 people

    0

    Private Charter - 40' Sailing Catamaran

    $995

    Maximum of 10 people

    0

    Captain Fee by the hour

    $30

    0

    Instruction Fee by the hour

    $125

    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