Great sailboat rentals near Baltimore, Maryland.

Sailing Reviews in Baltimore

1. LM

   Liz

   Welcome Aboard Optimystic! Create a beautiful memory on the water.

   Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

2. AV

   Ariel

   38-ft Hunter 376 Sailing Adventure in Annapolis

   We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

3. 

   Erika

   38-ft Hunter 376 Sailing Adventure in Annapolis

   We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.

4. 

   Lauren

   Charter 42' Lagoon Catamaran in Annapolis, MD

   We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

5. RK

   Richard

   34' Hunter Cruising Monohull In Rock Hall, Maryland United States

   Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!

6. JH

   Julie

   38-ft Hunter 376 Sailing Adventure in Annapolis

   A great day on the bay with Alberto and Grace. They are lovely and wonderful hosts—and a super safe and accommodating Captain/ First Mate!!