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About Cruise Annapolis
The Finest Fleet on the Chesapeake Bay We offer bareboat and fully crewed sailing charters. Charter for any length of time. Take a boat for a day sail or spend a few weeks exploring all the Chesapeake Bay has to offer. We provide full itinerary planning and provisioning services. We take care of the details so you don't have to. Take a sunset cruise and spend an evening aboard one of our boats on a romantic getaway with that special someone. Take a half or full day cruise around the Annapolis area. The Chesapeake Bay is well-known as an outstanding waterway for sailboat 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. We can coordinate sailing charters at our home base on the Chesapeake Bay and anywhere in the world. Interested in learning to sail? Our certified instructors can take you on a Learn to Sail vacation and help you obtain ASA certifications. Let Cruise Annapolis make your dream vacation a reality.
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1 - 10 of 18 reviews
Reviewed September 4, 2018

If you are looking for a Five-Star full service charter experience and marina, look no further than Cruise Annapolis. My wife and I just spent the Labor Day weekend sailing on the well-appointed “Serendipity” a Jeanneau 469. The boat was in mint condition and the...More

Date of experience: September 2018
1  Thank Murphyslure
Reviewed August 6, 2018 via mobile

Visiting Annapolis for the day, this cruise offered a simple, 45 minute informative tour at a very reasonable fee. Seating is plentiful, and full bar with fair prices was also within easy reach. If looking for a tour and greater knowledge of the history and...More

Date of experience: August 2018
Thank Veinleisure
Reviewed August 5, 2018

Staff was amazing! We chartered a birthday party day sail and loved every minute of it. Highly recommend this company!!

Date of experience: July 2018
1  Thank Mary Maille L
Reviewed July 30, 2018

This was my first time ever chartering a sailboat for a weekend, and I couldn't have asked for a better "bucket list" experience... We chartered Kalm Waters, a 2018 version of the Fontaine-Pajot Helia 44 catamaran. We were told that this was only the third...More

Date of experience: June 2018
Thank franklinmlee
Reviewed July 27, 2018 via mobile

We chartered the Jeanneau 440, Summer Salt. It was a 2018 model. What was there not to like. It was a beautiful sailing machine with all the comforts. The Summer Salt came in with the onboard generator INOP but the excellent maintenance man Jevon meant...More

Date of experience: June 2018
Thank dottopilot
Reviewed July 21, 2018

We have chartered sailboats many times with Cruise Annapolis and we keep coming back. The staff are all very friendly and very helpful. We things change there is no hassle. And we like the new additions to the fleet.

Date of experience: July 2018
Thank thoward9
Reviewed July 10, 2018

This was our first charter experience with Cruise Annapolis. From start to finish, we had a very good experience. Making the initial reservation was simple, keeping track of documentation was easy with their online dashboard and the check in was quick and informative. On our...More

Date of experience: July 2018
Thank Mark A
Reviewed June 24, 2018

See the Chesapeake Bay and the Chesapeake Bay Bridge on this cruise. We stayed inside the air conditioned boat. Saw great scenery and just relaxed. Great cruise.

Date of experience: June 2018
Thank Patsy S
Reviewed June 19, 2018 via mobile

Cruise Annapolis provided the best service of any of my 15 charters (Chesapeake and Caribbean) thus far. The boat was immaculate and the service/briefings/checking/checkout was not only friendly, knowledgeable and complete, but expeditious...the first time I have ever described a charter process as expeditious. Compliments...More

Date of experience: June 2018
Thank BAKlippenstein
Reviewed June 18, 2018

They have a great variety of boats for charter and keep them in excellent condition. The people are very helpful and pleasant to deal with. Strongly recommended.

Date of experience: June 2018
Thank davidU2072MV
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