The Finest Bareboat Fleet on the Chesapeake...

Experience the best new sailing yachts from Jeanneau and catamarans from Fountaine Pajot.  We are a boutique charter management company in the heart of Annapolis.  We offer luxuriously appointed, new and late model yachts which are privately owned and lovingly cared for. The Chesapeake Bay is well-known as an outstanding waterway for cruising. Protected waters, great anchorages, gorgeous natural scenery, bountiful seafood, unique, historic towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. 

Bareboat Yacht Charters

Cruise Annapolis offers luxury bareboat and crewed yacht charters on the Chesapeake Bay, onboard one of our world class Jeanneau monohulls or Fountaine-Pajot catamarans.  Most of our fleet consists of new yachts, the rest are nearly new. All are well equipped, privately owned, and meticulously maintained.  If you want to explore outside the Chesapeake Bay we have affiliate bases in the Bahamas, New England and the Caribbean.  

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Cruise Annapolis Sailing School

ASA Sailing Instruction

Learn to sail on the boat you ultimately want to own.  Catamaran sailing schools are our specialty.  Go out at any time, for any length of time, to learn with a certified instructional captain.  Your captain will work with you on any skills you are interested in learning; at a pace you are comfortable with. Our captains are fully experience on our Jeanneau and Fountaine-Pajot boats and will ensure you are comfortable in handling your new yacht.

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Business Yacht Ownership

Offset 80% to 100% of the costs of ownership with small business tax deductions and income.  Choose your boat, choose where you would like to keep it, use it as much as you like.  Let us help you set it up as a small business where tax advantages and income cover it's costs! We've already helped over 680 people do this. We're the acknowledged leaders in this field with 40 years of experience and success.  Call or sign up for our webinar.

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Let Cruise Annapolis Make Your Dream Chesapeake Sailing Vacation a Reality