Annapolis Sailing Charters: Sailing Chesapeake Bay

The concept of a “bareboat charter” – a boat rental without captain or crew – is very simple: A family or group of friends makes a reservation for a boat in advance, board the vessel at the designated time and place, receive a thorough check out of equipment and systems, and head to sea. During the charter period, the charterer determines the itinerary, sailing routes, destinations, etc. The charterer also assumes responsibility for the boat during the term of the contract; he or she acts as owner of the yacht.

Generally, the person skippering the vessel must have experience operating a boat of similar size (within five feet), displacement, and rig, and have comparable navigating experience to the planned itinerary. As part of the reservation process we discuss your experience. Our checkouts include a full systems checkout, and, if necessary, an underway check-out. We help you feel comfortable handling your yacht.

Cabin amenities will vary depending on the yacht you choose, but all yachts will be equipped with standard basics. For example, all yachts will have a fully equipped galley, including cooking and dining necessities, coffee maker, BBQ grill, Coast Guard Safety Equipment such as Adult PFDs, flares, first-aid kit, tool kit, charts, cruising guide, binoculars, and flashlight. Bed linens, towels, and inflatable dinghies are not included, but available for an additional fee.

If you prefer to hire a skipper of full crew, we have a list of qualified, experienced sailing professionals to choose from. Many people enjoy the security of having a captain aboard during the first few hours while they get their “sea legs” back. Others like to have that extra person aboard to help out throughout their trip.

To reserve the yacht of your choice, call us at 800-991-1776 to confirm availability. A 30% deposit will secure your reservation. We accept cash, check, Mastercard, Visa, or American Express. We will send a contract and Operator’s Manual by email. The balance is due 45 days prior to the charter.

If the charter is cancelled more than 90 days prior to your departure date, then your deposit if fully refundable. If between 89 days and 45 days prior to the charter start, a fee of $100 will be charged for boats 29’ to 39’ and $150 for yachts 40’ to 50’ and all catamarans. If the charter is cancelled between 44-15 days prior to the charter’s inception, a cancellation fee of $500 (loss of deposit) for all yachts will be charged. If a charter is cancelled 14 days or less prior to departure, there will be no refund. There will be a $50 rescheduling fee if the charterer elects to move the charter in lieu of cancellation; this is subject to availability of another similar yacht and must be more than 15 days prior to departure. No charters will be cancelled or rescheduled due to inclement weather or rain. However, if a named windstorm occurs at the time of your charter, rescheduling is permitted at no charge.

Additional expenses include fuel, holding tank pump-outs, provisioning, as well as the security deposit of either $1000 or $1500 depending on the size of the yacht chartered.

You can provision your own charter. But, if you want more time on the water and less time preparing for your trip, we offer an online provisioning service option based on your selections and specific needs. Please inquire for details.

Yes. We rent dinghies with outboard motors as well as linens and towels. Please consult your friendly charter reservationist for details.

Yes, you may check in anytime after 4 PM local time the evening before your charter for an additional $150.00.

Our office and our fleet are located in the Port Annapolis Marina on Back Creek in Annapolis, Maryland. Back Creek is one creek east of the Annapolis Harbor/City Dock area. There is plenty of parking, a nice bathhouse, pool, a ship’s store for marine items, and a cafe that offers food and beverages. Address: 7080 Bembe Beach Rd #211A, Annapolis, MD 21403.