The Blessing That Inspired Our Name

Front door decorated with two holiday wreaths on a dark green door, surrounded by beige and white siding and trim, with a plaque on the left side of the door and part of a brick wall and outdoor area visible.

In Navy parlance, "Fair Winds & Following Seas" is a blessing. Simply put, it's how the Navy says, "Good Luck!"

That’s the spirit of Fair Winds —our home, and now yours— in the heart of Annapolis. Built in the year 1850, this 19th-century landmark stands near the head of prestigious Prince George Street, a storied lane that has weathered centuries of change since the 1600s. Just a few steps from the United States Naval Academy, the Maryland State House, and the bustling city docks, it’s the perfect mooring for whatever course you chart through Downtown Annapolis.

From here, the town’s rhythm unfolds like the tide — cobblestone streets, gas lamps, and church spires leading you toward galleries, sail lofts, and centuries-old taverns that have welcomed sailors and statesmen alike. Wander past the Academy’s sea-worn gates, admire the hand-hewn brickwork of colonial homes, and take in the music, art, and maritime heritage that flow through every block.

Whether you’re setting sail from Ego Alley, exploring the city’s vibrant arts district, or simply strolling beneath the shade of crepe myrtles on Prince George, Fair Winds offers the ideal launch point. Here, Annapolis’s past and present meet on the breeze—where the sound of halyards on masts mingles with live jazz from a nearby café, and every step reminds you that this is a town built on the water, and by those who’ve loved it for generations.

So drop anchor, breathe deep, and let the charm of Annapolis carry you wherever the current leads.

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Living room with a tan leather sofa, two patterned throw pillows, a tufted ottoman, two large windows, a side table with a lamp, and wall decor
Close-up of a vintage brass door handle with a lion's head emblem, attached to an old, cracked white door frame. Inside the room, there is a wooden sideboard against a light blue wall and a painting hanging above it. Part of the adjacent room with a wooden dining table and chairs is visible in the background.

Aboard Fair Winds

Step inside this restored three-deck row home and let your shore leave begin. The moment you cross the threshold, you’re welcomed by a bright front parlor—anchored by a gas fireplace that flickers to life with a single click. It’s the perfect berth to swap sea stories over a cocktail or watch the steady “tide” of life along Prince George Street from the comfort of your armchair (or the front porch, weather permitting!).

A few paces farther aft, you’ll find the dining room—a natural gathering point for your crew—followed by a galley as cozy as it is capable. Outfitted with stainless-steel appliances, a deluxe Keurig complete with a milk frothier for lattes, and every gadget from blender to air fryer, it’s ready for whatever you’re cooking up. The galley’s second fireplace adds a touch of warmth, while the well-stocked pantry and “baking drawer” are standing by for anyone ready to hoist the whisk.

Just beyond the galley lies one of Fair Winds’ best-kept secrets: a private patio enclosed by centuries-old brick and shaded by a retractable awning. Whether you’re sipping morning coffee or charting a sunset happy hour, it’s your own hidden harbor in the heart of downtown. Fire up the gas grill for fresh seafood or a hearty steak, then dine under the glow of café lights as the sun dips below the yardarm.

In the midst of Annapolis’ lively harbor town, Fair Winds is your calm anchorage—a quiet oasis amid the bustle. When it’s time to turn in, choose from five beautifully appointed staterooms featuring king, queen, or twin berths dressed in soft linens, plush pillows, and comforters that rival the finest ship’s quarters. The baths, complete with walk-in showers and a luxurious soaking tub, offer the perfect place to wash away the day’s adventures.

Wherever you drop anchor, Fair Winds promises a soft landing and a stay as refreshing as a gentle breeze off the Bay.

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What Our Guests Are Saying…

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Location, Location, Location

Fair Winds sits in the heart of downtown Annapolis, just steps from the harbor and a block from the Yard, where sailboats creak at their moorings, chapel bells mark the hours, and the town hums with history. From morning coffee to evening dinners, you’re surrounded by waterfront walks, local art, and the glow of Annapolis’ restaurants and brick-lined streets — all easily explored on foot.

Chart Your Course

Curious to learn more about Fair Winds, her amenities, and all there is to explore in Annapolis? Drop us a line— we’re always happy to help you plan your perfect stay ashore.