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Page 5 of 8 • 177 listings
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Elisabeth
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️
AD
Alexandra
Cruise the Potomac On a Rinker 310
Cindy is so sweet and patient. She answered all of my questions and planned everything accordingly.We had an amazing experience!
MH
Marcus
$300hr | 15 ppl | Luxury Yacht
We had an amazing experience! We brought 15 people and everyone loved it! Clean boat, nice captain, and great speakers. Will definitely be booking again soon.
Cindy
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Our sailboat outing was absolutely perfect - peaceful, scenic and incredibly relaxing. The boat was pristine. Captain Charles and his wife were perfect hosts. Highly recommend!
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!
ZK
Zainab
Cruise the Potomac On a Rinker 310
Cindy communicates very well and is very flexible when it comes to time. I appreciate her patience and how comfortable she made the experience for us. Thank you!