⚓ Welcome Aboard

We’ve charted this FAQ to help smooth your voyage and answer the most common questions before you even need to ask. From check-in details to local favorites, we’ve tried to think like both hosts and guests to anticipate every swell and breeze along the way.

ABOUT THE PROPERTY

🏡 What is Fair Winds?

Fair Winds is a luxury 1850s historic home located at 159 Prince George Street in Downtown Annapolis — one of the closest private residences to USNA Gate 1 and the waterfront. Guests enjoy a fully private home with 5 bedrooms (6 beds), 3.5 baths, spacious dining areas, a gourmet kitchen, and a garden patio.

🛏️ How many bedrooms and beds are there?

Fair Winds has 5 bedrooms and 6 beds total:

• Primary Suite (2nd Floor): 1 Queen bed

• Guest Room 1 (2nd Floor): 1 King bed

• Guest Room 2 (2nd Floor): 2 Twin beds

• Guest Room 3 (3rd Floor): 1 Queen bed

• Guest Room 4 (3rd Floor): 1 Queen bed

• We also provide a Pack-N-Play with mattress and multiple crib sheets, as needed.

🔟 How many guests can stay overnight?

Up to 10 overnight guests (12 with advance approval).

🛏️ Are all bedrooms upstairs?

Yes — all sleeping quarters are on the 2nd and 3rd floors. The main staircase is wide and comfortable for a historic home; no bedrooms are on the ground floor.

👣 Is the home suitable for guests who have difficulty with stairs?

For an 1850s home, the main staircase is shockingly generous and the preferred route for guests with mild mobility concerns. For those with significant mobility limitations, the lack of first-floor bedrooms may make Fair Winds challenging.

🏡 Is the entire home rented, or can I book a single room?

Fair Winds is available only as a full-home rental, offering complete privacy.

🚗 Does the home have parking?

Fair Winds does not have private off-street parking, as is normal for historic downtown Annapolis. However, there are several easy paid and free options within walking distance.

🅿️Street Parking (Quick/Short-Term)

• Prince George Street: Often 2–3 spaces near the house. Paid via the ParkMobile App (typical downtown meter app).

• On-street time limits: Usually 2-hour maximum during the day; but free overnight. Enforcement can be active, so be sure to pay on ParkMobile and move your car when time expires.

🏢 Parking Garages - Great for all-day parking while you explore Annapolis:

• Hillman Garage: Closest public garage — about a 3–5 minute walk. Drive up Main St, turn left on Gorman St (just past CVS).

• Gott’s Court Garage: Around a 10-minute walk. Gateless entry; pay with phone and license plate (Metropolis/QR system) or app.

• John Whitmore Garage: Also ~10-minute walk and another good all-day option.

• Calvert Street Garage (State Garage): Excellent choice for free parking — free all day on weekends and free after hours (typically evenings until early morning).

✅ Free & Discounted Parking Tips

• Calvert Street Garage: Free all day on weekends, free evenings/overnight (subject to posted hours — check signage).

• Holiday & special promotions: The city sometimes offers free meter hours or promotions like Park, Shop & Dine validations; these vary by season.

⏱️Longer Stays / Advance Parking Options
If you’re planning a longer booking or want guaranteed spots in advance, you can check parking availability and reserve ahead via PremiumParking.com — they list downtown spaces, pay-by-app options, and multi-day or monthly parking where available.

If you need help choosing which garage works best for your plans (especially for multi-day/overnight), just let us know!

🚭 Is smoking allowed?

Fair Winds is a strictly smoke-free property, indoors and out.

🐾 Are pets allowed?

Pets are welcome only with prior written approval and may not be on furniture or bedding.

AVAILABILITY, RATES, & BOOKING

💼 What are your rates?

Rates vary by season, weekday/weekend, and events in Annapolis. For the most accurate pricing, view our live calendar and booking portal available through this site.

🌙 Is there a minimum stay?

Yes — 2 nights for most of the year. Special event weeks (Navy Football, Commissioning Week, boat shows) may require longer stays.

🗓️ Do you allow weekend rentals?

Absolutely. Many USNA families stay with us for football weekends, Plebe Parent visits, and alumni events.

💻 Do you offer direct booking?

Yes — and direct booking avoids OTA fees. Guests often prefer it for cost savings and smoother communication.

⚓ Do you offer USNA alumni or military discounts?

Yes — alumni and veterans are always welcome. Just ask for the “Anchors Aweigh” discount code.

🚀 Is Commissioning Week available?

Fair Winds is honored to host Navy families for this once-in-a-lifetime milestone.

• CW stays are 9 nights (covering the full 10-day period).

• Rates are by request-only due to limited availability and high demand.

• Most years are fully booked years in advance, but you can contact us to check.

• Payment plans are simple and flexible: 10% at signing, remaining payments annually until 90 days before CW.
  

⛔ What is your cancellation policy?

• Full refund if canceled 14+ days before check-in.

• No refund within 14 days of arrival.
  

🔎 How do I check availability for specific dates?

Visit our live calendar on fairwindsdta.com. If your dates appear blocked, feel free to reach out — occasionally our internal calendar can offer solutions.

LOCATION & PROXIMITY

🔱 How close is Fair Winds to USNA Gate 1?

Exceptionally close — a 3–4 minute walk straight down Randall Street. If you're visiting a Mid, attending Navy Football, or touring the Yard, this is one of the most convenient stays in Annapolis.

🚶 Can we walk to the stadium?

Yes — the Navy–Marine Corps Memorial Stadium is a 20–25 minute walk, or a short ride.

⛵ How far is downtown Annapolis?

You are in downtown. Steps to:

• City Dock

• Main Street

• Market House

• Waterfront restaurants

• Water Taxi

👩🏻‍🍳 What restaurants are within walking distance?

Many — including some of the best in Annapolis:

• Big Cheese (2 min) – best sandwiches in town

• Choptank (6 min) – waterfront seafood

• The Goat (30 seconds) – casual, delicious

• Iron Rooster (2 min) – famous breakfast

• Galway Bay (5 min) – beloved Irish pub

• And dozens more. Full list in the Welcome Book.

☕ Where is the nearest coffee?

Rise Up Coffee, Bitty & Beau’s, Starbucks, and Brown Mustache are all 1–4 minutes on foot.

CHECK-IN/OUT & STAY DETAILS

⏰ What time are check-in and check-out?

• Check-in: 4:00 PM

• Check-out: 11:00 AM

⏳ Do you offer early check-in or late check-out?

When possible, yes — depending on housekeeping schedules. Fees may apply.

🗝️ How do we enter the home?

Fair Winds is equipped with a smart lock (access code provided within 24hrs of arrival).

🛜 Is the home equipped with Wi-Fi and streaming?

Yes — high-speed Wi-Fi with Google TV, YouTubeTV, Netflix, and Prime Video.

❄️ Does the home have air conditioning and heat?

Yes — central HVAC, controlled by a smart thermostat between the kitchen and dining room.

🫕 Is there a grill?

Yes — a gas grill with propane is available on the patio.

🔥 Is there a fireplace?

Yes — two gas fireplaces (kitchen + family room). They are secured from April 1–August 31 for safety.

🍽️ Is the kitchen fully equipped?

Absolutely — a chef-friendly kitchen with:

• Full appliances

• Keurig

• Small appliances (in vintage wood pantry)

• Basic spices and pantry sundries

🎥 Do you allow small gatherings or filming?

Fair Winds welcomes small, quiet, pre-approved daytime use, such as filming an interview or gathering for a meal. Parties, events, or large groups are not allowed.

👨‍👨‍👦‍👦 Can we host a meal for visiting friends or family?

Yes — the dining room comfortably hosts 10+ for meals, which is why so many families use Fair Winds as their home base for Navy milestones.

SPECIAL REQUESTS

👩🏻‍💻 Is the house good for corporate retreats or work trips?

Yes — many companies use Fair Winds for small off-sites.

💡 What if we forget something?

We’re happy to ship lost items (shipping charges apply).

PROXIMITY TO EXPERIENCES

🪪 Can we visit the US Naval Academy?

Absolutely — bring a government-issued ID and enter through Gate 1. Tours operate Mon–Sat and last ~90 minutes.

🚤 How close is the Water Taxi?

Just down the block at City Dock — about 2 minutes away.

🗺️ What are the best things to do within walking distance?

• Waterfront promenade

• William Paca House (half a block away)

• Maryland State House

• Live music at Rams Head

• Sailing tours on the Woodwind

• Shopping on Main Street & Maryland Ave

HOUSE POLICIES

📢 Are parties allowed?

No — this is a quiet residential street in DTA. Unauthorized events may result in cancellation and/or fees.

🔕 What are the quiet hours?

10 PM – 8 AM (city ordinance + house rules).

📸 Is there an exterior security camera?

Exterior-only, for safety and compliance. No interior cameras — ever.

🌊 Still adrift with questions?

Send us a signal! We’re always happy to help ensure your stay is smooth sailing from bow to stern. Reach out anytime — the crew at Fair Winds is standing by at the helm.