We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. St. Augustine, FL/
    3. Water Activities/
    4. Sailing/
    5. St Augustine Shared Sunset Sailing Charter

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
    Greetwell

    Trusted by leading vacation properties and hotels, Greetwell helps travelers feel at home wherever they go. Enjoy curated experiences that carry you from the comfort of your stay into the heart of the local community.

    Safe & Secure Payments

    Guest Support

    • Help Center
    • (650) 414-7338
    • [email protected]

    Company

    • About
    • Nominate Providers
    • Hospitality Partners
    © 2025 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 2
    Gallery image 3

    St Augustine Shared Sunset Sailing Charter

    Sail at sunset past St Augustine landmarks with a small group and professional crew

    From$179/ person

    Duration

    2 hours

    Ideal For

    Up to 12 people

    Includes

    Captain & crew, Free parking

    Highlights

    Make it a night to remember on a 2 hour small group sunset sail in St Augustine. Feel the ocean breeze as you pass landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse with a professional crew.

    • Sail along the historic waterfront at sunset
    • See Castillo de San Marco, Bridge of Lions, and the Lighthouse
    • Relax while the professional crew handles the vessel
    • Park conveniently with free marina parking
    • Purchase food and beverages on site
    • Arrive 10 minutes early for boarding

    What's Included

    • Captain and crew
    • Sailing vessel
    • Free marina parking

    Things to know

    A minimum of 2 guests is required to depart; maximum 12 guests. Wear non-marking shoes and avoid hard soles, high heels, and black rubber soles. No pets or smoking on board; alcohol must be purchased in the office before departure.

    Cancellation policy

    Cancel 72+ hours before for a full refund of your deposit. Cancel 71–25 hours prior: 50% of the charter cost is non refundable. Cancel within 24 hours: full charter cost is non refundable. Rescheduling 71–25 hours prior incurs a $100 fee. Weather-related cancellations for dangerous conditions are excluded.

    Meeting location

    3076 Habor Drive, St Augustine, FL 32084

    Perfect for

    • Couples seeking a romantic evening with historic views
    • Small groups wanting a relaxed waterfront experience
    • History buffs touring St Augustine's landmarks
    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 #DRG5V2

    Person

    $179

    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