A smiling couple taking a selfie, with a woman and a man, against a background of trees. The image is part of a graphic with a dark teal background, a circular photo with a yellow border, and the word 'Ahoy!' written in yellow text.

At the Helm

We’re Joshua (USNA ’09) and Amanda (USNA ’10)— two Naval Academy grads who first crossed paths on the trails of Philmont and have been charting life’s adventures together ever since. From deployments to new horizons, our journey has been fueled by service, curiosity, and a shared love of the seas and mountains alike.

Joshua still serves proudly as an active duty U.S. Marine Corps V-22 pilot, while Amanda, a former Navy Surface Warfare Officer, now steers her course in the Defense Tech world. When we’re not chasing our next adventure, you’ll find us hiking, exploring new ports of call, or simply enjoying a sunset over the Severn.

Anchored in honor, travel, and a deep love for Annapolis, we’ve designed our stays to reflect the same values that shaped us at the Academy— excellence, authenticity, and attention to detail. Each stay is crafted to give guests more than just a place to drop anchor— it’s an invitation to experience the heart and soul of Annapolis, the harbor where our story began, and the place we’re proud to call home.

A hand-drawn compass rose with North, South, East, and West labels, displayed over a background with horizontal light blue and white stripes.
An illustrated map showing the Main Gate of U. S. Naval Academy in Annapolis, Maryland, with a domed building and trees in the background.

Where Tradition Meets the Tides:

United States Naval Academy

Set on the banks of the Severn River, where the waters of the Chesapeake Bay meet the soul of a seafaring nation, the United States Naval Academy has stood as both a fortress of learning and a beacon of service since 1845.

Founded by Secretary of the Navy George Bancroft, the Academy was established to bring structure, science, and moral grounding to the art of naval warfare—a place where America’s future naval leaders could learn to navigate not just the seas, but the storms of command, courage, and character.

The Academy’s story began in the heart of historic Annapolis, on the grounds of what was once Fort Severn, a small Army post guarding the harbor. From that humble start, Bancroft’s vision took shape: a school that would turn midshipmen into officers—blending academic excellence with the rigors of seamanship and the unshakable honor that defines the Navy and Marine Corps.

Over time, the Yard has grown into a symbol of duty, discipline, and discovery. Its stately Beaux-Arts architecture, commissioned in the early 1900s and designed by Ernest Flagg, remains a masterpiece—anchored by Bancroft Hall, the largest dormitory in the world and home to every midshipman during their years on the Severn. Nearby, the Chapel’s copper dome rises above the treetops, its bell tolling across the water like a call to purpose, while beneath it rests John Paul Jones, the “Father of the American Navy,” in a marble crypt as solemn as a ship’s keel.

Each corner of the Yard tells a story: the grit of Plebe Summer, where the newest midshipmen are forged; the precision of Parade on Worden Field, where centuries of drill and ceremony echo across the river; and the Midshipmen’s March-On at Navy-Marine Corps Memorial Stadium, where every name engraved on the façade honors a fallen hero and the battles that shaped the sea service.

Life at the Academy moves to a rhythm all its own—a cadence that blends tradition and tide. It’s the sound of reveille at dawn, the creak of boats in Dorsey Creek, and the chant of “Go Navy, Beat Army!” echoing through the cold air of December. It’s the shared bond between classmates who’ve weathered both storms and sun, carrying lessons of integrity, teamwork, and resilience far beyond the Yard’s gates.

Today, the Naval Academy remains one of the world’s preeminent institutions of leadership and service—a place where science and seamanship, intellect and honor, all converge under the Navy’s timeless watchwords: Honor, Courage, Commitment. From its earliest days to its modern mission in the digital age, the Academy continues to prepare officers to lead with clarity, compassion, and an unwavering moral compass—whatever seas they’re called to sail.

So when you stroll along Prince George Street and hear the morning bells drift across the water, you’re not just hearing a school at work: you’re hearing the living heartbeat of the Navy’s past, present, and future. For in Annapolis, the call of the sea never fades; it merely changes watch.

History, Beauty & Tradition

Just a Block Away

From Fair Winds, you’re less than a five-minute stroll from the main entrance (Gate 1) of the United States Naval Academy — where future Navy and Marine Corps officers have been trained and inspired since 1845.

Steeped in history, honor, and heritage, “The Yard” is one of the most beautiful campuses in the country and a true must-see while you’re in port. Tours are offered Mon-Sat, lasting about 90 minutes, and are a fantastic way to experience the Academy’s story and setting.

Getting There: Turn right out the front door, then left on Randall Street. Walk one block — you’ll see Gate 1 across the street. Bring a government-issued ID to enter through the main gate. The Visitor Center, just to the right of the entrance, is a great place to start.

A national treasure sits just beyond your doorstep; a place where tradition meets tide, and the spirit of the sea runs deep. Don’t miss it!

The emblem of the U.S. Naval Academy featuring a shield with a sailing ship and book, surrounded by a gold trident, anchor, and laurel wreath, with the motto 'SCIENTIA' and the words 'NAVAL ACADEMY' and 'U.S.'.