Explore America's Sailing Capital

Charter a Yacht in Annapolis with AYS Yacht Charters

Annapolis, Maryland is America’s Sailing Capital that thrives on its rich maritime culture and relaxed coastal lifestyle. From its beautiful shorelines and towns to the historic treasures waiting in every port, the Chesapeake Bay provides a premier cruising destination.

Enjoy an unforgettable sailing vacation and create memories that last forever!

Experience sailing on more than 200 miles of the Chesapeake Bay. There are destinations for everyone!

  • Explore the abundance of peaceful coves and captivating harbors.
  • Discover the thrills of the Baltimore Harbor and its vibrant nightlife. Delight in the charms of the seaside town of St. Michaels. Relax in the complete seclusion of Solomons Island.
  • Indulge in some of the best local seafood, including the famous Maryland crab cake, while visiting historical ports and scenic waterfronts.

The Chesapeake Bay offers a world of possibilities!

Book your vacation today.

Our Fleet

AYS Yacht Charters’ fleet includes luxury Beneteau sailboats and Lagoon Catamarans which are well equipped and expertly maintained.

In partnership with Navigare, a world-renowned charter operator, we make booking a dream vacation simple and convenient.

Featuring the Lagoon 42 "E-Lane"

Charter Fleet Boat Spotlight
Lagoon 42 “E-Lane”
Built 2019
Guests: 6 + 2
Cabins: 3
Heads: 3
AC: Yes
Generator: Yes

Lagoon 42 cabin layout 3

Frequently Asked Questions


Yes, you need to hold a sailing license to rent a boat in most of our destinations. This is what is called a “bareboat charter”. However, you may book a skipper through Navigare if you don’t have a sailing license or prefer a hands-off approach during your holiday. Some of our larger yachts over 50 feet require a dedicated crew. This experience is called a “crewed charter”.

The British Virgin Islands do not require a sailing certification; however, a strong sailing resume is preferred.

Should you want to verify the eligibility of your sailing credentials and license, feel free to contact us. Please note that ASA is recognized and accepted throughout Europe. To charter a boat up to 30 tons, you need to have a Bareboat Chartering level (ASA 104). Above 30 tons (i.e. Lagoon 450 and larger) Advanced Coastal Cruising (ASA 106) is required.

You will be asked to provide a sailing resume outlining your experience and skills with docking, mooring, and anchoring. Our catamarans 50 ft and above may require a dedicated crew, depending upon your level of experience and certification.

If you wish to opt for a checkout ride, please contact us to arrange this ahead of time.

See our packing tips on our blog post: Packing tips for a sailing vacation


Your Charter yacht will be located at the Bert Jabin Yacht Yard, at the dock in front of the charter basin.
Upon arrival, please contact the office and staff on site for assistance. Should you arrive after 19:00 (7:00 PM), we will leave the boat unlocked and ready for you, with a note to your attention on the office door. The check-in will take place the following morning.

We do not currently have one-way sailing routes in the Chesapeake.

Embarkation is at 14:00 (2:00 PM) but may be subject to base discretion.  
Disembarkation is at 12:00 (Noon).

Check-in is performed by an AYS Yacht Charters Team Member and the skipper and one crew member. They inspect the boat from stem to stern, and check that all the equipment is in place and functioning properly.

During check-in, you will also receive instructions on the operation of the specific yacht model you’ll be chartering. You and your crew will be given instructions regarding the use of toilet, holding tank, and propane for cooking. Should you have any questions or concerns, please ask our staff! If you detect any malfunctions, just call our service team! When you sign the takeover, ensure that any existing damage has already been written down. At check-out you will go through the boat again and be given the chance to rate our service.

Our office hours are from 8:00 – 17:00 (5:00 PM). If you arrive after hours, you will find a note on our office door with the location of your boat. Your boat will be left unlocked with the lights and refrigeration turned on.

The skipper always has full responsibility for the boat, therefore contracting skipper insurance is highly recommended. If you hire a professional skipper through Annapolis Yacht Sales and Charter, he will be responsible for any and all damages onboard.

Should loss or damage occur as the consequence of your gross negligence, damage costs may apply at the discretion of our base manager and will be discussed with you during check-out.

It is recommended that the boat be returned to the base the night before check-out, usually on Friday by 18:00 (6:00 PM). Check-out can take place on Friday as long as there is day light, or on Saturday morning. Disembarkation is at 12:00 (Noon) every day.

If the cancellation is more than 120 days prior to embarkation, the cancellation fee is $575 US.
If the cancellation is between 119 and 60 days prior to embarkation, you pay for 50% of the charter fee.
If the cancellation is 59 days or less before embarkation, you are responsible for 100% of the charter fee.
We strongly recommend purchasing travel insurance to cover for losses caused by unforeseen events.

There are no trains or busses from the local airport (BWI) to Annapolis. The most efficient way to get to the Annapolis base is by car. Parking is limited to load / unloading at embarkation site. Parking is limited overall at the Marina. Ridesharing and carpooling are recommended. You may take a taxi from the airport or utilize the local UBER transportation. Prices vary according to service.

Fuel, cruising tax, moorings in all marinas other than home base, and all other personal expenses.

You may sleep aboard your boat on the night before your charter (upon availability). For early accommodation, embarkation is at 17:00 (5:00 PM). Check-in the next morning is at 9:00 AM. The cost is 65% of the daily charter rate.

3 days is the minimum charter length with the exception of peak periods (New Year, Spring break, etc).

No, you do not have to clean the boat before you leave! However, the boat should be left in the same condition as you found it, i.e. dishes clean and put away, kitchen equipment in its original place, sheets & towels folded, and any garbage taken off the boat. Make sure to double check the lockers so as not to leave any personal items behind!

Charter An Annapolis Boat Today