Design your Sailing Charter 

Customize your Private Sailboat charter ON THE CHESAPEAKE BAY

Based out of Rock Hall, located on Maryland’s eastern shore, Shardana Sailing Charters offers you a range of cruising options.  We offer half-day, full day, sunset, overnight destination cruises, full weekend, and multi-day cruising charters,. We also offer an expanded variety of special event sails including marriage proposals, wedding parties, corporate team building and other special cruises. Our trips can be laid-back or adventurous, you decide how you want sail. We can design your charter so you can swim, visit a historic sight, anchor out to star gaze and/or enjoy dinner ashore at a restaurant—How you sail on Shardana is (nearly) totally up to you! We can custom design your sailing adventure to meet your specific needs and fulfill nearly any of your requirements. Our 43-foot semi-custom built sailboat can accommodate up to six passengers per trip, including families, friends, groups, or even small office retreats.  For larger groups and corporate events, we do partner with other captained owned and operated sailboats to accommodate larger groups.   Sailing on a yacht is a personal and intimate experience and our captains and crew are here to serve you.    All of our cruises are private sailing charters so you decide with whom you sail and in many ways, how you sail.   If you would like to learn how to sail or improve your skills, Shardana Sailing Charters can provide you with sailing instruction. All of our captains are certified sailing instructors and have sailed in the Caribbean and Mediterranean seas; Some have sailed all over the world. (See our Captains Bios here). You will cherish the life-long memories made while sailing Shardana for years to come.  That's why our motto is….Creating Memories and Sail Your Story!

Join us on a sailing charter and sail any, or all, of the 205 miles that mark the northern and southern boundaries of America’s most famous sailing center, and the largest bay in the USA— the Chesapeake Bay!   We can customize any cruise for up to six passengers. All half-day and full-day excursions include soft drinks and snacks.  S/V Shardana has three state rooms, one of which is reserved for the captain.  Therefore, please understand that for groups larger than four people on multi-day cruises, two passengers may be sleeping in the convertible beds located in the main salon.  

Shardana Sailing Charters has partnered with Pearl on Main to provide you with delicious catered options for your cruise.  All you need to do is contact Pearl on Main to place your order. We can also arrange to have the Osprey Point Inn Restaurant provide catered options for your charter. Alternatively, you are more than welcome to bring your own food and beverages for your trip.

Please call us for details at 215-238-1635 .

Prices are for the entire boat, NOT per person:

Half-Day Trips: $435/3.5 Hours

Day Trips:  $839/7 hours

Sunset Cruise: $375/2.5 hours

Overnight Package: $1099, up to six passengers, boarding anytime and ending 24 hours the following day.  Includes captain and fuel, does not include provisions or docking fees.

Marriage Proposal Package: Call for Details and Pricing

Romantic Package: $1099 for one couple (no other passengers), boarding anytime and ending 24 hours the following day.   Includes captain and fuel, does not include provisions or docking fees.

Full Weekend Cruise Package: $2400, up to six passengers, boarding anytime Friday after 12:00 pm; cruise ends around 4:00 pm on Sunday afternoon.  Includes captain and fuel; does not include provisions or docking fees.

Mid-Week Special: $3300, Monday through Friday cruising;  Boarding anytime after 9:00 am on Monday and disembarking  12:00 pm on Friday.   Includes captain and fuel. Fee does not include provisions or docking fees.

Seven Day Adventure: $4900, Saturday morning 9am through the following Saturday morning 9am. Includes captain and fuel. Fee does not include provisions and marina docking fees. Call for booking.

Custom Multi-Day Cruises:  Call for pricing.

Corporate Team Building and Leadership Training: Check out our customizable corporate programs here.

Flotilla Cruising:  We are partnered with other captained vessels to provide multi-boat flotilla cruising experiences.

Special Events:  For birthdays, engagements, weddings, anniversaries, corporate events or corporate training, Shardana Sailing Charters will make your event all the more memorable.  We also work with the Boy Scouts of America as well as Sea Scouting, and religious organizations.