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    1. Local experiences/
    2. St. Augustine, FL/
    3. Water Activities/
    4. Yacht Charters/
    5. Private Sunset Sail Along Historic Bayfront

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    Private Sunset Sail Along Historic Bayfront

    Experience a luxury sunset sail with stunning views of St Augustine’s historic landmarks.

    From$595

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Private yacht, crew, parking

    Highlights

    Set sail on a luxury yacht for a memorable sunset cruise along St Augustine’s historic bayfront. Enjoy iconic sights and a relaxing atmosphere with friends or family.

    1. Sail past landmarks like Castillo de San Marco and the Bridge of Lions
    2. Relax on a luxury yacht with professional crew
    3. Take in panoramic views of the downtown skyline
    4. Purchase food and beverages on board
    5. Enjoy a comfortable and scenic evening on the water

    What's Included

    1. Private yacht charter
    2. Professional crew
    3. Free parking at the marina

    Things to Know

    Maximum of 6 guests per vessel, not including captain and crew. Please wear non-marking shoes and avoid red wine, spray tanning products, and smoking on board. No pets are allowed.


    FAQs:

    Q: How long is the sail?

    A: The sunset sail typically lasts about 2 hours from departure to return.

    Q: Is the tour narrated or guided?

    A: Yes. The captain or crew points out landmarks and shares local history.


    Q: Will we see wildlife?

    A: You may spot dolphins, birds, and other marine life, though sightings are not guaranteed.


    Q: Is there a bathroom on board?

    A: Yes. The boat has a restroom with a sink and toilet.


    Q: Can people get seasick?

    A: It’s uncommon, but motion sickness can occur. Staying mid-vessel and watching the horizon can help.


    Q: Can we bring our own food and drinks?

    A: No. Food and drinks are available for purchase on board.


    Q: What should I wear and bring?

    A: Wear comfortable, weather-appropriate clothes, non-slip shoes, and sun protection. Bring a light jacket for cooler evenings.

    Cancellation policy

    Cancel before 72 hours for a full refund. Cancel between 71–25 hours and 50% is non-refundable; a $100 rescheduling fee applies. Cancel within 24 hours and the full cost is non-refundable. Weather-related cancellations are excluded.

    Meeting location

    Inside Camachee Cove Marina at 3076 Harbor Drive, St Augustine, FL 32084. Once you reach the marina, continue past the security guard building and we are located on the first floor of the 5th structure on the right.

    Perfect for

    • Couples seeking a romantic evening with historic St. Augustine views
    • Small groups celebrating special occasions on the water
    • Families wanting a relaxing 2-hour escape with local 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 #D9F6WF

    Private Charter - 35' Sailing Vessel

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    Private Charter - 44' Sailing Vessel

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    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