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With Captain
Classic pilothouse ketch with sheltered space and plenty of character, offering a relaxed, comfortable platform for cruising local Annapolis and Chesapeake waters.
Trip is run with a dedicated captain included, so guests can relax while an experienced skipper handles the sailing and guides the route around Annapolis waters.
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AI Overview
Owner's Description
Step aboard a classic Nauticat 331 for an exclusive private sailing experience in Annapolis. This comfortable pilothouse sailboat offers a more refined way to experience the waterfront, whether you’re looking for a relaxed harbor cruise, sightseeing around Spa Creek and the Severn River, sailing the Chesapeake Bay, or simply enjoying time on the water with friends and family. The pilothouse design offers the flexibility to enjoy the boat from inside or outside, with a protected, air-conditioned space for especially hot days or less-than-perfect weather. This is not a crowded party boat. It is a private, relaxed experience focused on enjoying the boat, the views, and the Chesapeake Bay atmosphere. Depending on weather and conditions, we can sail, motor, anchor, swim, stop at waterfront restaurants, or simply cruise and take in the scenery. The boat features a shaded cockpit, air-conditioned pilothouse, cabin and galley, comfortable cockpit seating, classic teak character, and plenty of charm. A solid wood rail runs around the boat, offering a more substantial and secure feel than the flexible lifelines found on most sailboats. Movable cushioned seating can be arranged throughout the decks, and the spacious bow has room for all six guests to relax while underway. Guests are welcome to bring food and drinks. I provide plates, cups, utensils, a cooler with ice, and a small gas BBQ grill. Catering can also be arranged. Perfect for couples, families, small groups, birthdays, visiting guests, relaxed celebrations, sunset cruises, or anyone looking for a more refined, private Annapolis boating experience without the crowds. Captained by a USCG Master credentialed captain based in Annapolis. Capacity: up to 6 guests. Listed pricing is based on up to 4 guests. Please include your group size when requesting a booking. Pricing may vary for smaller groups, larger groups up to 6 guests, longer trips, custom itineraries, or special requests. I’ll confirm the final details and price before accepting the booking.
Optional Add-ons
These options can be added during checkout.
Catering
$1 per trip
Paddleboards
$80 per trip
Parking
$1 per trip
Ice
$5 per trip
Floating Bed
$200 per trip
Pick-up Options
$1 per trip
Stephen
11 total bookings
- Capacity
- 6 guests
- Sailing
- Cruising Monohull
Reviews
(4 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
5 photos have been added by reviewers who booked this listing.
CJ
Camille
Terrific trip. Steve was a great captain! Super helpful with planning a perfect day on the water.
KG
Kathleen
Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!
RB
Richard
Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.
LF
Linda
Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!
Stephen
11 total bookings
I’m a USCG Master credentialed captain based in Annapolis. I operate a classic Nauticat 331 pilothouse ketch and offer relaxed, private boating and sailing experiences around the Annapolis waterfront, Spa Creek, the Severn River, and nearby Chesapeake Bay waters. My focus is safety, comfort, and a low-key personal experience. Depending on weather and conditions, we can sail, cruise the harbor, anchor, enjoy the views, swim when appropriate, or arrive at a waterfront restaurant by boat. Longer outings and overnight trips to places like St. Michaels, Rock Hall, Baltimore Inner Harbor, or a quiet anchorage may also be available by request. This is not a crowded party boat. It is best for couples, families, visiting guests, small groups, birthdays, sunset cruises, or anyone who wants a private and comfortable time on the water. Guests are welcome to bring food and drinks, and I’m happy to customize the outing with you based on your interests, the weather, and the conditions.
Features & Details
- Nauticat
- 331
- Capacity: 6 people max
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Near 25 Market Space
Annapolis, Maryland, 21401
United States
Departure Location
38.9770404,-76.4860379
Annapolis, Maryland, 21401
United States
Cancellation Policy
Free cancellation up to 7 days before your trip.
Additional Terms & Information
Safety comes first. Weather cancellations or rescheduling are at the captain’s discretion, but the goal is always to provide a safe and enjoyable day on the water, not to keep a guest’s payment when the experience would be poor. Summer thunderstorms are common in Chesapeake Bay forecasts and often pass quickly, so a chance of storms does not automatically mean cancellation. If severe weather appears likely to affect a significant portion of the charter, we may delay, reschedule, or cancel. Likewise, even if conditions are technically safe, an extended period of rain may simply not make for an enjoyable trip. In those situations, I will work with guests to be as flexible, reasonable, and accommodating as possible. Guests concerned about weather close to their booking date are welcome to reach out so we can discuss the forecast and available options. In practice, we have adjusted dates and start times when possible to work around weather and other circumstances. Guests should arrive on time and ready to board. Late arrivals may shorten the trip. No-shows are handled under the platform cancellation policy. Guests may bring food and drinks. Unsafe intoxication, drugs, disruptive behavior, or failure to follow captain instructions may result in refusal of boarding or early return. Swimming is only allowed with captain approval and when conditions are safe. Children must be supervised by an adult at all times and wear life jackets when required. While life jackets are available on board, children’s sizes should be discussed in advance to ensure an appropriate fit is available.
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