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Our charters: sailing Chesapeake Bay

We have just the right boat for you and your crew...

A large quality fleet of yachts from which to choose

From modern monohulls to exciting catamarans, any of our boats will have you sailing from Annapolis in comfort and style.

View our full fleet list

Location, location, location

Annapolis harbour

Annapolis Bay Charters is located at The Port Annapolis Marina on Back Creek. This is a full-service marina with a pool, private bathhouses, breakfast/sandwich shop, picnic/grilling areas, water-taxi service to downtown shops and restaurants, parking. At anytime during your charter you may come back and use your slip and the facilities at no additional cost. Back Creek also offers easy access to the Chesapeake Bay.

Frequently asked questions

What is a 'Bareboat Charter'?

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.

What experience do you require?

Generally, we require that the person chartering the vessel has experience operating a boat of similar size (within five feet), displacement, and rig, and navigating experience. As part of the reservation process we will talk with you about your experience. Our checkouts include a full systems checkout, and, if necessary, an underway check out. We want you to feel comfortable handling your yacht.

What is included with the boat?

Although cabin amenities will vary depending on the yacht you choose, all yachts will be equipped with the 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, along with a Tool Kit, Charts, Cruising Guide, Binoculars, Flashlight, etc. Bed linens, towels, and inflatable dinghies are not included, but available for an additional fee.

Do you have captain and crew available?

We have a list of qualified, experienced captains, and crew available from which you can choose should you so desire. 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.

How do I reserve my charter?

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

What if I have to cancel my 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 rescheduling is permitted at no charge.

What additional costs should I expect?

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.

How do I provision my charter?

We offer an online provisioning service option, based on your selections and specific needs. This way you can have more time on the water and less time preparing for your trip. Please inquire for details.

Do you have dinghies and linens available?

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

May I arrive the evening before my charter begins?

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

Where are you located?

Our office and our fleet are located on Back Creek in Annapolis, Maryland. Back Creek is one creek east of the Annapolis Harbor/City Dock area. We are in the Port Annapolis Marina. 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 Road, Suite 211, Annapolis, MD 21403.

Worldwide destinations with Dream Yacht Charter

Visit Dream Yacht Charter

Sail the places you’ve only dreamed of. The Caribbean, the Mediterranean, the Indian Ocean, the Chesapeake Bay or the Pacific Ocean. With over 40 locations worldwide and more than 700 boats from which to choose, Dream Yacht Charter is everywhere you want to sail.

Choose your vacation by destination, Bareboat Charter, Luxury Crewed Charter or By the Cabin vacation packages.

For more details speak to one of our
Planning Specialists at 800-991-1776 or email our team


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