Welcome Aboard!
We are a boutique sailing charter company based between the historic seaside towns of Oxford and St. Michaels, Maryland, cruising the serene waters of the Tred Avon and Miles Rivers and out into the storied Chesapeake Bay. Our charters are crafted for those who crave both elegance and adventure—relaxation with a hint of the unexpected, coastal beauty with a touch of indulgence.
Our Story
Inspired by the timeless romance of Chesapeake sailing, our company was created for guests who want more than just a boat ride—they want an experience. Sailing the Chesapeake on a catamaran is a blend of smooth speed, wide-open comfort and endless coastal scenery. With twin hulls skimming the water, the boat stays level and stable while the breeze fills the sails. We blend classic maritime heritage with the comfort of a private, personalized charter. Whether you prefer a champagne sunset or a breezy daytime voyage, every sail is designed to feel effortless, luxurious, and unforgettable.
Where Adventure Meets Calm
The Tred Avon and Miles Rivers are some of the Chesapeake’s most captivating waterways:
- Wide, open breezes perfect for smooth sailing
- Miles of scenic shoreline and secluded coves
- Majestic ospreys, blue herons and quiet marsh grasses
- A peaceful river that opens to the vast, iconic Bay
Here, a sail can be as serene—or as spirited—as you want it to be. Sit back and savor the quiet rhythm of the water or feel the thrill as the sails fill and the bow slices forward.
The Charm of Oxford
The port of Oxford offers old-world coastal beauty: colonial history, quiet tree- lined streets, and waterfront views that feel untouched by time. After your journey, enjoy local seafood, explore marinas, or arrive in true Eastern Shore style—aboard the ferry, just as travelers have for generations.
The Rhythm of St. Michaels
St. Michaels welcomes boaters with a charming blend of nautical history and easy-going coastal atmosphere. You’ll cruise into a protected harbor lined with classic sailboats and waterfront restaurants, where docks are just steps away from boutique shops, iconic seafood restaurants and the famed Chesapeake Bay Maritime Museum. The town’s walkable streets are shaded with old oaks, colonial homes and friendly locals who love to share stories of the Eastern Shore. It’s the kind of port where you can tie up, wander the historic district, enjoy fresh crab on a sunny patio and watch the painterly sunset settle over the Miles River – quiet, picturesque and made for lingering.
A Private Escape on the Water
Every charter is reserved exclusively for your group. Perfect for:
- Romantic escapes and proposals
- Family adventures
- Celebrations on the water
- Out-of-town guests
- Those who want to see the Bay in style
Relax on deck with curated comforts, take the helm under guidance, or simply sip a drink and watch the shoreline drift by. It’s relaxed effortless cruising – big views, salty air and the easy freedom of life under sail.
Sailing with Intention
- Elegance without formality
- Adventure without pressure
- Safety, comfort, and personalized servic
- Memories that last long after you step back onto the dock
Your Chesapeake Adventure Awaits!
Sunrise whispers, warm breezes, golden sunsets, star-lit returns—every sail is a moment in time. Join us and discover the Chesapeake the way it should be experienced: beautifully, privately, and with a touch of salt-air magic.
Meet the Captain
At the helm of every charter is Captain Ridge, a lifelong sailor, maritime enthusiast, and storyteller of the Chesapeake. Raised on the water and guided by a deep respect for the Bay’s tides, wildlife, and traditions, the captain brings both professionalism and passion to every voyage.
With years of experience sailing the Tred Avon, Choptank, and wide-open waters of the Chesapeake Bay, the Captain knows every shift of wind, hidden cove, and scenic shoreline. Guests can expect a calm, confident presence—someone who makes sailing feel effortless, safe, and inviting, whether you’re an experienced sailor or stepping aboard for the very first time.
Beyond navigation, the captain is part host, part historian, and part adventurer. You may hear stories of Bay lore, learn the basics of sailing, or be invited to take the helm for a hands-on experience. For those who prefer to recline with a glass in hand, the captain ensures a smooth, luxurious ride with nothing required except enjoyment.
Safety is always the top priority, followed closely by comfort, hospitality, and an appreciation for the beauty of the Chesapeake. Under the Captain’s guidance, every journey becomes more than a charter—it becomes a
memory.
Meet Catamaran ALPENGLŌ
Alpenglō is a 47-foot PRIVILÈGE Catamaran. Privilège Catamarans are a French brand of luxury cruising cats known for their high-quality construction, bespoke interiors, and capability for long passages & ocean crossings. Each Privilège catamaran is a semi-custom build, allowing owners to personalize their boats with choices ranging from interior layout and materials to equipment and electronics. This approach results in unique vessels tailored to the specific needs and desires of their owners. You’ll find Alpenglō offers an elegant living space, spacious salon seating & cockpit, queen-sized beds in every cabin, beautiful wood finishes and special touches throughout.
What exactly is an Alpenglō?
An Alpenglow is natural optical phenomenon (like a rainbow) that lights up mountains just before sunrise or right after sunset when the sun is still below the horizon yet its rays still catch the high peaks. Instead of shining directly, the light scatters through the atmosphere, washing the slopes in warm shades of rose, peach and lavender while the valleys remain cool and shadowed. The effect is quiet and magical – an otherworldly glow that makes the mountains look like they are lit from within. Those who spy it are so very lucky! After years of mountain living, Alpenglō’s owners named the boat after this phenomenon, something that always brings a smile.