The Best Sailboat Rentals Near Cape Charles

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

We celebrated our 10th anniversary on Faith and couldn’t be happier. Captain Ian personalized the journey for us and guided us along the way. He was exuberant, caring, and checked in with us to make sure we were having a great time. He asked if we wanted to learn sailing and taught us a few things, which was so cool and unexpected. We are excited to sail again to learn more and see the beautiful sites NYC has offer!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

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!

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!

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

been through a few yacht but Joe is the best host. He makes sure you will have a wonderful trip. And his boat is gorgeous, clean and spacious!