Private Sailing Charter: Why It’s the Ultimate Way to Experience St. Augustine
There is no better way to truly feel the soul of St. Augustine than from the deck of a private sailing charter. While the nation’s oldest city dazzles from the cobblestone streets with horse-drawn carriages and centuries-old architecture, its real magic unfolds on the water. Augustine’s waterfront. From the water, the Castillo de San Marcos stands sentinel against fiery sunsets, the Bridge of Lions frames postcard-perfect views, dolphins arc through your wake, and the entire downtown skyline glows like something out of a dream.
A private sailing charter with St. Augustine Sailing delivers an experience that shared boat tours, crowded sunset cruises, and even most land-based activities simply cannot match: complete exclusivity, total flexibility, and luxury tailored to your group and your group alone. Whether you’re celebrating an anniversary, planning the perfect proposal, gathering three generations of family, hosting a small corporate retreat, or simply stealing a quiet escape for two, stepping aboard one of our luxury yachts at Camachee Cove Yacht Harbor turns an ordinary vacation day into a memory you’ll recount for decades.
Here’s exactly why a private sailing charter is the ultimate way to experience St. Augustine — and why thousands of our guests say they’ll never go back to crowded group tours again.
St. Augustine Was Literally Built for the Water
Founded in 1565, St. Augustine is the oldest continuously occupied European-established settlement in the continental United States. Every major chapter of its story, from Spanish galleons and pirate raids to the Flagler era and modern-day tourism, played out on the shores of the Matanzas River, the Intracoastal Waterway, and the Atlantic Ocean. The city’s most iconic landmarks were designed to be seen from the sea: the coquina walls of the fort, the twin spires of the Cathedral Basilica catching the golden hour, the St. Augustine Lighthouse standing proud on Anastasia Island.
From land you fight crowds, traffic, and obstructed sightlines. From the water on a private sailing charter, those same landmarks become your personal backdrop. There are no strangers leaning into your photos, no fixed narration blasting over loudspeakers, and no rush to keep a tour-bus schedule. Your skipper slows when a pod of Atlantic bottlenose dolphins appears, lingers when the sunset turns the sky ablaze, and steers toward hidden salt-marsh creeks when you ask. The city becomes your own private stage.
The Private Difference
Shared tours can be a fun way to get on the water for anyone watching their budget. But if you’re looking for a truly personal, elevated experience, a private sailing charter in St. Augustine is in a different category. It’s calmer, more comfortable, and designed around your group instead of a set script.
1. True Privacy & Intimacy
Our luxury sailing yachts host a maximum of 12 guests, your family, your friends, or just the two of you. That means your sail feels like a private celebration, not a public outing:
- No fighting for the best spot at the rail
- No awkward small talk with strangers
- No competing for seating
- The entire deck, the conversation, and the champagne are yours alone
Couples celebrating engagements, anniversaries, proposals or vow-renewal moments, regularly tell us the moments felt even more magical because there wasn’t another soul on board except their guests and the captain and crew (who conveniently doubles as discreet photographer). It’s truly theirs, quiet, unrushed, and beautifully private.
2. Your Schedule, Your Itinerary
On a shared tour you’re locked into someone else’s timetable. On a private sailing charter, the answer to almost any request is “Of course.” Your captain can tailor the pace, route, and vibe to what you want most.
- Prefer a morning departure for soft light and smooth water? Done.
- Want to linger when the dolphins show up? Absolutely
- Want more history… or less talking and more peaceful sailing? Your call.
- Feel like staying awhile along the bayfront to see the lights? We’ll drop anchor.
You don’t have to “keep up” with a tour schedule, you get to settle into the experience.
3. Personalized Service That Feels Like Family
When it’s just your group aboard, the whole charter becomes more attentive and persona. Your U.S. Coast Guard-licensed skipper and crew are focused on you from the first minute.
They learn names quickly and tailor the experience to your group
They adapt beverages and snacks to preference (yes, even Grandma’s ginger ale)
They can set the mood with your playlist via Bluetooth audio
They customize the tone: local history, nature, sailing education, or calming quiet
It feels less like “customer service” and more like being welcomed aboard by people who genuinely love what they do.
4. Luxury That Feels Like Your Own Private Yacht
Our fleet features modern, impeccably maintained Lagoon and Jeanneau sailing yachts, clean, comfortable, and designed for a relaxed, upscale vibe.
You’ll enjoy features like:
Spacious decks with comfortable seating (and room to spread out)
Shaded cockpits with bimini tops for sun protection
Bluetooth sound systems for easy music
Clean blankets and pillows for breezier evenings
Refrigerators with complementary water.
Options for chilled sparkling wine, craft beer, or sodas
Optional upgrades like gourmet charcuterie or fresh fruit platters
It’s the difference between “taking a boat tour” and stepping onto a yacht experience that feels like it was created just for you.
Private Charter vs. Shared Tour — at a glance
Private charter: your group only, flexible timing, custom route, personalized service
Shared tour: mixed groups, fixed schedule, set route, general narration
- Discover which type of charter is for you!
Signature Private Sailing Charter Experiences
St. Augustine Sailing offers a private sailing charter for every mood, season, and milestone.
Romantic Sunset Private Sailing Charter
Our most popular option. Depart Camachee Cove as the late-afternoon light turns golden, raise a toast with chilled sparkling wine, sail past the Lighthouse and downtown, then anchor or drift while the sky explodes in pinks and oranges over the historic district. Hundreds of couples have gotten engaged on this exact sail and many more have renewed vows with the fort as witness.
Dolphin & History Private Sailing Charter
Perfect for families or history lovers. Cruise the Intracoastal and Matanzas River while your skipper points out dolphin pods (almost guaranteed) and shares stories of Spanish treasure fleets, Henry Flagler’s railroads, and the Timucuan people who lived here for thousands of years before Europeans arrived.
Nights of Lights Private Sailing Charter (Nov–Jan)
St. Augustine’s world-famous Nights of Lights is regularly ranked among the top ten holiday light displays on the planet by National Geographic. Seeing millions of white lights reflect across the water from a private yacht, sipping hot buttery apple cider or a glass of wine, is pure magic. These charters sell out months in advance so book early.
Custom Full-Day or Overnight Private Charters
Anchor off Cumberland Island to see wild horses, sail down to Marineland, or spend the night aboard under the stars. If you can dream it, we can usually make it happen.
The St. Augustine Sailing Difference
- Modern, award-winning sailing yachts kept in Bristol condition
- Passionate, licensed captains who love sharing “their” city
- Transparent, all-inclusive pricing (no hidden dock fees, gratuity, or fuel surcharges)
- Eco-conscious practices — we leave nothing but wake
- Optional sailing lessons during your charter if you want to take the helm
- Membership programs and fractional ownership paths for guests who fall in love and never want to leave
Your St. Augustine Story Starts on the Water
A private sailing charter isn’t just another activity to check off the vacation list, it’s the moment your trip becomes legend. The proposal that ended in happy tears as the sun dipped below the lighthouse. The multigenerational family trip where teenagers finally put down their phones to watch dolphins race the bow. The quiet anniversary morning when you remembered exactly why you fell in love thirty years ago. The solo sail where St. Augustine quietly became your soul’s home port.
That’s the quiet, powerful gift of a private sailing charter, and that’s why our guests keep coming back year after year, some of them for decades.
Ready to write your own chapter? Book your private sailing charter today and see why St. Augustine was always meant to be experienced from the water.
For more information and to stay updated, visit www.sta-sail.com and follow them on social media @StAugustineSailing.
