The Best Boat Rentals Near Middle River

38-ft Hunter 376 Sailing Adventure in Annapolis

Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.

43ft Cruiser Express Yacht for Daily Charter

We went on a boat ride with Captain Rob for my boyfriend's birthday and it was an amazing experience. We were able to bring our own drinks and Captain Rob had a cooler to store them in and keep them cold so we did not have to carry much. The initial boat that we booked was not available on the day of our ride so Captain Rob upgraded our boat to a much larger yacht without charging us anything additional. He was very kind and knowledgeable and answered all of our questions without making us feel inexperienced. Everything was on time and the experience was flawless and exactly as I had hoped it would be. We will absolutely be back this summer for longer trips and with more people. Highly recommend Captain Rob!

38-ft Hunter 376 Sailing Adventure in Annapolis

This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.

42ft Party Yacht Best of Baltimore 2024-25 Winner!

Captain Brian was amazing! He was so helpful, professional, and made sure everything went smoothly for me and my guests. The weather was perfect, and he was very accommodating to make sure we had the best experience possible. We had so much fun out on the water! I truly appreciate how easy and enjoyable he made the whole trip. It was such a fun and memorable experience I’m definitely looking forward to booking again and would absolutely recommend anyone to book with him.

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

Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

42ft Party Yacht Best of Baltimore 2024-25 Winner!

Cap Brian is AMAZINGGGGGGGGGGGGGGGGGGGGGGGGGG! He is very sweet and his communication is fast and top notch, he is very patient and fun. I had captains who were non-social and just wanted your money. He was VERY professional, social, safe and he made me and my guest feel very comfortable, and safe as well. All I will say is HE IS WORTH IT GO BOOK YOU WILL NOT BE DISAPPOINTED AT ALL! I will definitely be booking with him again and again, and again!! 10 STARS!