St. Augustine by Boat:
A Coastal Journey Through History and Beauty

You have to see St Augustine by boat to really see it! Consider that from the deck of a sailboat, St. Augustine’s charm unfolds in a way that land simply can’t capture. Exploring the city by boat offers a fresh perspective — where ancient forts, towering lighthouses, and wild marshes reveal their secrets from the water’s edge. Unlike crowded streets or car tours, a sailboat journey brings you closer to the heart of America’s oldest city, all within a leisurely 15-mile radius.

At St. Augustine Sailing, we’ve crafted outings that make this experience unforgettable — picture sunset cruises that turn the evening into magic or high tea on the water with a side of history. Whether you’re a local or a visitor, seeing St. Augustine by boat transforms the way you connect with its past and present. Ready to set sail? Let’s dive into what awaits you on our sailing adventures.

The Unique Perspective of St. Augustine by Boat

Seeing St. Augustine by boat unveils a side of the city that land-bound visitors miss, offering unobstructed vistas and a deeper connection to its maritime soul. On land, the Castillo de San Marcos is a stone giant surrounded by bustling tourists, but from a sailboat on Matanzas Bay, it rises majestically from the shore, its cannons silhouetted against the sky. The St. Augustine Lighthouse, a black-and-white beacon on Anastasia Island, feels distant from the road — yet from the water, it towers over the coastline, guiding you with timeless grace.

Unlike noisy motorboats and crowded tour boats, our vessels offer the the most intimate way to get to know St Augustine, sailing as we slip through shallow inlets and rivers, revealing hidden corners of the coast. There’s a freedom in leaving the shore behind — the breeze in your hair, the rhythm of the waves, and the chance to see dolphins or seabirds up close. It’s not just a tour; it’s a journey into tranquility and wonder. Whether you’re tracing the city’s 450-year history or soaking in its natural beauty, St. Augustine by boat shifts your perspective, making every moment feel like a discovery. From the water, this historic gem shines brighter than ever.

Key Highlights Within 15 Miles of St. Augustine by Boat

A sailboat’s range of about 15 miles round-trip from St. Augustine opens up a treasure trove of sights, each transformed by the water’s perspective. From historic forts to wild waterways, here are the highlights you’ll encounter with St. Augustine Sailing, all within a day’s journey.

Historic Downtown and Matanzas Bay

Sailing along Matanzas Bay, the heart of St. Augustine’s historic downtown comes alive. The Castillo de San Marcos stands guard, its weathered stone walls rising directly from the water’s edge — a view that feels both imposing and intimate from your sailboat. The Bridge of Lions stretches across the bay, its elegant arches and lion statues mirrored in the rippling tide, especially striking at dusk. From land, these icons are framed by streets and crowds, but exploring St. Augustine by boat brings history to life in a quieter, grander way. The bayfront’s colorful buildings glow against the horizon, offering a postcard-perfect scene. At St. Augustine Sailing, our educational charters dive into the city’s 450-year story — imagine learning about Spanish explorers or pirate raids while anchored just offshore. It’s a front-row seat to the past, with the sea as your guide.

St. Augustine Lighthouse and Anastasia Island

Cruising past Anastasia Island, the St. Augustine Lighthouse commands attention. From the water, its black-and-white spiral stripes soar against the sky, a beacon that’s guided mariners since 1874. On land, trees and buildings obscure its base, but St. Augustine by boat showcases the lighthouse in all its coastal glory, framed by the Atlantic’s edge. Nearby, Anastasia State Park’s sandy shores stretch out, dotted with dunes and seabirds — perfect for spotting ospreys or dolphins playing in the surf. The view feels wild and untouched, a contrast to the city’s bustle.

Our family-friendly charters make this a hit for all ages, with plenty of chances to snap photos or learn about the area’s ecology. Whether you’re a history buff or a nature lover, this stretch of coastline delivers a serene, unforgettable glimpse of St. Augustine’s dual identity — historic and natural. By far, this is one of St. Augustine’s best boat rides!

Intracoastal Waterway and Tolomato River

Venture north or south along the Intracoastal Waterway or up the Tolomato River, and St. Augustine’s wild side emerges. These sheltered waters, easily reachable within 15 miles, wind through marshes and estuaries teeming with life — think manatees drifting lazily or herons stalking the shallows. From a sailboat, you’ll spot hidden coves and grassy islands that cars can’t reach, offering a peaceful escape from the mainland.

The Intracoastal’s calm currents make it ideal for a relaxing sail, while the Tolomato River feels like a secret passage through time. St. Augustine Sailing’s eco-adventures or private charters let you tailor the trip — bring binoculars for birdwatching or simply unwind as the scenery unfolds. This is St. Augustine at its rawest, a blend of solitude and discovery that only the water can unlock. Within a day’s sail, these routes prove there’s more to the city than its historic core.

St. Augustine Sailing's Charter Offerings

At St. Augustine Sailing, we turn the magic of St. Augustine by boat into tailored experiences that elevate your time on the water. From romantic sunsets to an elegant spa day, our charters bring the city’s coastal charm to life — here’s how.

Sunset Cruises -
A Magical Experience

There’s something undeniably special about a sunset from the water. As the sun dips below the horizon, casting fiery reds and purples across Matanzas Bay, St. Augustine’s skyline glows. On land, trees and buildings can block the view, but a sunset cruise with St. Augustine by boat offers an unobstructed front-row seat to nature’s show. Our sunset charters, departing from Camachee Cove Yacht Harbor, let you unwind on a luxury sailboat as the day fades into night. Whether you opt for a shared sail or a private escape, the gentle sway of the boat and the vibrant colors reflecting off the sea create a memory that lingers. Sip a glass of wine, feel the breeze, and watch the city transform — a perfect ending to any day in St. Augustine.

Elegance Afloat - Culinary Sailing Experiences

Indulge in the perfect pairing of gourmet cuisine and coastal charm with St. Augustine Sailing’s exclusive Culinary Sailing Experiences. Whether you’re toasting the sunset on our Sunset Tasting Cruise or enjoying a chef-prepared meal under the stars on a private or shared Dinner Cruise, every moment is crafted for unforgettable flavor and ambiance. Our Brunch Sails—available as private or shared experiences—offer a luxurious way to start your day, featuring fresh fare and breathtaking morning views. For a more refined experience, step aboard our High Tea Adventure, where heirloom teapots, delicate pastries, and tranquil seas combine to honor tradition and elevate your afternoon. Every voyage is a feast for the senses, blending culinary artistry with the magic of sailing along St. Augustine’s historic waterways. Whether you’re celebrating a special occasion or simply treating yourself, our Culinary Sailing Experiences promise something truly memorable.

Luxurious Charters

Escape the ordinary and indulge in pure relaxation with St. Augustine Sailing’s Luxurious Sailing Experiences. Treat yourself to our Tide of Tranquility, where you’ll enjoy either a 3-hour or 5-hour sailing escape complete with spa services aboard a private yacht. Let the gentle sway of the sea melt your stress away as our licensed spa therapist pampers you with facials, massages, and soothing treatments, all while you sip refreshing beverages and nibble on light, nourishing refreshments.

For an unforgettable night on the water, our Overnight Stay experience offers two serene options: dockside comfort or the romantic solitude of a mooring ball in downtown St. Augustine. Whether you’re seeking a wellness escape, romantic retreat, or peaceful night under the stars, our luxury sailing adventures are designed to rejuvenate your body and soul while showcasing the beauty of coastal Florida like never before.

Charters For Everyone

At St. Augustine Sailing, we believe the magic of sailing should be accessible to all. That’s why we offer a wide range of sailing charters to suit every dream—and every budget. From our First Sunday Sails at just $50 per person to unforgettable Dolphin Tours and St. Augustine History Sails, there’s something for everyone to enjoy. No two sailors are alike, and our custom charters reflect that. Whether you’re planning a romantic escape, a family outing, or an educational adventure exploring the city’s rich history and marine life, we’ll help you create the perfect experience. Small-group charters ensure a personal touch, while our knowledgeable captains guide you through hidden waterways, scenic vistas, and historic landmarks. Whether it’s your first time on the water or your fiftieth, St. Augustine Sailing makes every sail a unique journey worth remembering. Let us help you set your perfect course!

Book Today and let the coast inspire you take St Augustine’s by boat.