The Best Cruising Catamaran Rentals in Virginia

Charter 44' Orana Cruising Catamaran In Deale, Maryland

We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!

Lagoon 42 Catamaran in Chesapeake Bay

I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

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!

Charter 44' Orana Cruising Catamaran In Deale, Maryland

This trip was above and beyond ! The boat is spacious, beautiful, and comfortable. Everything was seamless and we spent a wonderful time sailing, swimming, and relaxing on the various parts of the boat.

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!