The Best Boat Rentals Near Saint Michaels

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

Captain McCoy made us feel right at home from the start. He is incredibly friendly and welcoming, and he handled our large group of ladies very well! He is a host and a captain! The boat itself was even better than expected, and Captain McCoy helped us enjoy all the amazing amenities (the speaker, the mounted cameras for group pics, the giant beanbag chairs for lounging on the bow). We will book with him again!

43ft Cruiser Express Yacht for Daily Charter

Here’s a polished version of your review: --- We had an incredible time on our sunset cruise around Annapolis! Captain Rob was the perfect host—welcoming, accommodating, and thoroughly professional. The boat was immaculate and just right for our group, offering plenty of space and comfort. Rob made sure we caught the best views of the sunset and always prioritized our safety. It was a smooth, relaxing experience from start to finish. We would absolutely book again and highly recommend this tour to anyone looking for a scenic and memorable way to enjoy Annapolis from the water. It was absolutely perfect!

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

We had another wonderful experience renting from Sunmi! The first one was a year ago. He continues to keep the boat in excellent condition - this is the boat in which he takes out his family, and it shows! And he himself is a wonderful person with whom it is a pleasure to interact. We will definitely go back with him next time we go boating in the Chesapeake Bay!

38-ft Hunter 376 Sailing Adventure in Annapolis

Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.

Private Yacht Charter: On 40ft Regal Commodore

Our boat ride with Dennis was awesome. His boat is very well maintained with plenty of space to make sure everyone always has a good seat and view. He took us to two great spots he knew about, one for swimming, and one for sunset viewing. During the ride he was always asking questions to make sure everyone was taken care of and having a good time. The kids (ages 7-8) were giggling non stop the first time he went full throttle, so this experience is definitely recommended for families.

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

Scott worked with me and accommodated time change at last minute due to weather - he gave my kids and I a super relaxing time on his boat, we had a blast on the pull float! I hope to book him again next summer for sure!