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    1. Local experiences/
    2. St. Augustine, FL/
    3. Water Activities/
    4. Sailing/
    5. Sail In Style Nautical Portrait Experience

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    Flexible cancellations
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    Sail In Style Nautical Portrait Experience

    Capture stunning portraits while enjoying a luxury sailing adventure along St. Augustine’s scenic coastline.

    $299/ person

    Duration

    2 Hours

    Ideal For

    4 to 12 people

    Includes

    Sailing, portrait session, digital photos

    Highlights

    Set sail on a luxury yacht for a two-hour experience blending elegant sailing with a professional portrait session. Enjoy breathtaking views of St. Augustine’s historic waterfront while each guest receives a private photo shoot.

    1. Select from five iconic St. Augustine backdrops for your portraits
    2. Relax aboard a premium sailing yacht with comfortable seating
    3. Receive five professionally edited digital photos per guest
    4. Enjoy a boutique-style, small-group atmosphere
    5. Experience a scenic cruise past all five landmarks
    6. Benefit from a licensed captain and dedicated crew

    What's Included

    1. Two-hour luxury sailing experience
    2. Professional portrait session with in-house photographer
    3. Five edited digital photos per participant

    Youths 15 and under must be accompanied by a parent or guardian. Youths 16 and older require a signed liability waiver. Minimum of 4 bookings required to depart. Limited availability to maintain an intimate setting. No substitutions for the photographer are permitted.


    FAQs

    Q: How long is the Sail In Style experience?

    A: The experience lasts two hours, including both sailing and individual photo sessions.


    Q: How many photos do I receive?

    A: Each guest receives five professionally edited digital photos delivered via private email link.


    Q: Can I bring my own photographer?

    A: No. All portraits are taken exclusively by the in-house photographer to ensure consistency and quality.


    Q: What should I wear for the photos?

    A: Solid colors photograph best. Avoid all-white or all-black outfits, large prints, and high heels. Barefoot or flat sandals are recommended aboard the yacht.


    Q: Will other guests be on board?

    A: Yes. This is a shared experience with up to 12 guests total, but each participant has a private 10-minute photo session.


    Q: What happens if fewer than four people book?

    A: The sail requires a minimum of four bookings to depart. Guests will be notified to reschedule or receive a refund if the minimum is not met.

    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 aboard the vessel dockside.

    Meeting location

    3076 Harbor Drive, St Augustine Florida 32084

    Perfect for

    • Couples seeking a romantic St. Augustine getaway with professional keepsakes
    • Friend groups wanting upscale photos without stiff studio vibes
    • Families celebrating milestones on the water in historic Florida
    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 #CJVVRT

    $299 / person

    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