The Best Sailboat Rentals Near Riviera Beach

Woman-owned luxury with transparent pricing - read our 5-star reviews!

We had such a good experience with Jessica and Captain Dan! The boat was supplied with basic needs and a bathroom! There is a Bluetooth speaker and a bean bag in the front of the boat so that you can lounge there if you'd like. The communication up front was excellent and easy to follow. I highly recommend this experience. Myself and the 5 others in tow had the best time! Thank you!

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!

Woman-owned luxury with transparent pricing - read our 5-star reviews!

Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!