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Page 1 of 10 • 240 listings
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LE
Lara
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
My girlfriends and I had the best time celebrating a bachelorette party with Captain Brian and his beautiful boat! From the very start Brian had quick communication and was helpful answering our questions. The actual boat was so nice, with a rustic charm. It comfortably fit all 10 girls. Brian made the day extra special - he’s so kind and fun. Would definitely recommend to this others and even hope to do another trip again!
JS
Jen
STARZ -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!
SG
Stephanie
Special End of Season Sunday pricing for 8 to 13 passengers
My friends and I rented Captain Russell’s boat for a wedding weekend celebration and had the best time! The boat was beautiful, and Captain Brian made the whole experience super enjoyable. Highly recommend!
MF
MaryBeth
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Highlight of our trip was booking this catamaran ride with Captain Paul. From the view, to the swim and dolphins, it was wonderful. Don’t hesitate to book a trip!
DC
Donte
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!
M
Mark
Ask about our SPECIAL end of season Sunday Savings! Captain included.
Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.