The Best Boat Rentals Near Ocean Pines

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

We arrived and were greeted by the friendliest person Mr. Tim. He was wonderful, very hospitable and attentive. He anticipated all of our needs for the evening. The waterfront scenery was surprisingly beautiful, seeing all the different styles of homes. An added bonus while coasting to the cove, we encountered a family of dolphins. It was a very exhilarating night. The view of the sun setting over the water was perfect from the float. The boat was quite spacious, enough for an impromptu dance party with the blue aura lights while finishing the evening. If you are looking for a fun filled evening full of laughter, and excitement. This is the thing to do

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

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

The best! Truly enjoyed the experience with my wife. I highly recommend. Professional and personable. You will enjoy your time with him no doubt, I can’t wait to book with him again soon.

The Big Kahuna 18 Passenger Tiki Boat

Justin and his crew did a great job! We planned a cruise for a bachelorette party. It was the perfect high energy, fun environment that allowed everyone to enjoy. They were highly accommodating and assisted us in any way we needed.

Private Yacht Charter: On 40ft Regal Commodore

Captain Dennis is absolutely fantastic. Great communication, fabulous boat and amenities, and a wonderful captain. Would highly recommend!

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!