The Best Boat Rentals Near Chesapeake Beach

Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island

We had the greatest time with Captain Tim and Chill Time cruises! From day one, Capt. Tim has been very responsive, communicative, and friendly! On the day of our charter, everything was amazing! From the onboard mimosas to the beautiful charcuterie plate, and the greatest inflatable float ever! We have zero complaints and we look forward to coming back again! Thank you for everything!!

Quick Private Annapolis Harbor Boat Ride - Oceanus 12 VST Inflatable

Stephen is the type of guy who makes the whole experience of boating on the water a once-in-a-lifetime feat. From his warm demeanor to his approach to helping each guest he takes on, to his allowance of people driving his own boat, his guidance along the way makes each and every guest wanting to come back for more. As soon as he met me outside the marina, he steered us on his boat into the waters of Annapolis Harbor, and did not hesitate to explain the landmarks we would be seeing alongside how boating actually works. For a newbie, he guided me on the logistics of how to drive his boat, which is something I thought was very warm and interesting. Stephen is an extremely friendly guy and is willing to do anything it takes to make his guests feel respected, relaxed and willing to know all about “the way of the water”. I learned a lot from him, and was left feeling fulfilled by my visit. I highly recommend Stephen to anyone who wants to do boating on the waters of Annapolis because he is a very knowledgeable and friendly person who always goes the extra mile.

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt. Alberto was wonderful, his boat beautiful and we had the most glorious morning on the water. It was seamless, efficient, lovely and our whole family said it was the highlight of there vacation and week.

$1100 2hrs| 39ft Regal | 12 Guests | Annapolis

An absolutely fantastic experience from start to finish! The captain was wonderful and the scenery was breathtaking, making for an unforgettable trip out on the water. The boat was spotless, the booking process was a breeze, and everything ran like clockwork — couldn’t recommend it more highly!