Great sailboat rentals near Annapolis, Maryland.

Sailing Reviews in Annapolis

1. KC

   Kevin

   April, 2024

   Charter 42' Lagoon Catamaran in Annapolis, MD

   Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!

2. RH

   Roger

   April, 2024

   Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

   Great vessel. Well maintained. Up to date equipment. Very relaxed.

3. JR

   Josh

   September, 2023

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   Highly highly recommended! The boat is as advertised, but the real treat is spending time with Captain Alberto, and his wife Grace, who are such warm, loving, and knowledgeable people. They clearly know their boat inside and out, so you will never feel uncomfortable. But they also encourage guests to help running the boat and they have the knowledge to help everyone understand what is happening. Most importantly, they are simply fun to be around and a joy to talk to. I can't wait to sail with them again!

4. BC

   Brian

   August, 2023

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   Across the board, a wonderful charter that exceeded expectations. It'd been some years since my wife and I had been on the water and what we expected was a day out refamiliarizing ourselves and just enjoying the Bay -- But Capt Alberto skillfully combined pleasurable sailing with private sailing lessons, a naval architecture primer, and boat buying 101. We can't wait to get back out on the water again with Alberto!

5. 

   Michael

   August, 2023

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   We had an amazing experience today with Alberto and his lovely wife. The boat was beautiful. I’m interested in learning to sail and as soon as Alberto found that out he spent most of the day teaching me about sailing. He has deep knowledge and was very good at explaining things. They also both made us feel like good friends rather than customers. We will definitely sail again with them soon!

6. JW

   Joe

   July, 2023

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   Captain Alberto and his wife, Grace, are such great hosts. They worked with us to reschedule because of a lightning storm. Communication was great. The boat is very nice and comfortable. We had a great time and learned a lot too. We will book with them again!