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.

What Inspired Our Name

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 lovingly restored 1850 home tucked along storied Prince George Street in the heart of Annapolis. Just steps from the United States Naval Academy, the Maryland State House, and the bustling city docks, it’s a perfect mooring for whatever brings you to town.

From here, Annapolis unfolds at an easy rhythm: cobblestones underfoot, church spires overhead, boats gliding through Ego Alley, and music drifting from tucked-away taverns that have welcomed sailors and statesmen for generations.

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

Map of Annapolis, Maryland highlighting Naval Academy, USNA, Fair Winds, and Navy-Marines Memorial Stadium.

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.

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. Just beyond the threshold, a sunlit front parlor welcomes you — anchored by a gas fireplace that springs to life with a click. It’s the perfect berth for swapping sea stories over a cocktail or watching the steady “tide” along Prince George Street.

A few steps aft, the dining room gathers your crew before leading to a galley that’s as cozy as it is capable. Stainless appliances, a deluxe Keurig with frothier, and every gadget from blender to air fryer stand ready for duty. A second fireplace adds warmth, and a well-stocked pantry await.

Just beyond lies a hidden harbor: a private brick patio shaded by a retractable awning. Sip morning coffee, chart a sunset happy hour, or grill the day’s catch beneath café lights as the sun dips below the yardarm.

Amid Annapolis’ harbor bustle, Fair Winds is your calm anchorage. Five inviting staterooms — king, queen, or twin berths dressed in soft linens — promise restful nights, while spa-like baths with walk-in showers and a soaking tub wash the salt from the day.

Drop anchor and enjoy a stay as refreshing as the Bay breeze.

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What Our Guests Are Saying…

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Screenshot of a Yelp review for Fair Winds Inn in Chapel Hill, North Carolina, praising its charm, comfort, and convenient location.
Review from Sarah about her stay at a home, praising its location, cleanliness, and responsive host.
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Review for Nicole from Carmel, Indiana, praising her as a responsive and flexible host.
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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.