Come relax on a sailboat!

Book a sail

A private charter on our spacious catamaran or classic sailboat

Looking for something beyond what we offer on our regular tours? We’re happy to help design a custom experience for you.
Book a Private Charter

Join us for a sunset cruise with local craft beer

Enjoy a selection of local craft beers while watching the sun dip below the horizon…as we drift into the night.
Book a sunset Cruise

Special event: Dog Social Sail

Bring your pooch out on the water! Come join a relaxing sail for some dog (and human) connection. We'll meet at Happy Dog Boutique in Fells Point, which will be open for you to pop in and get treats or shop before we take off. Then we'll spend two and a half hours sailing out to the Key Bridge on our 40' Leopard catamaran. We'll drop you off two blocks away at Crescent Marina. There are limited dates and spots available so book soon!
Join the dog sail

What Guests Are Saying

"Logistics wise, the entire process is hassle- and worry-free. Rob is a great communicator and very accommodating (the snacks and beverages were wonderful!). All in all, highly recommended as a relaxing gateway from the busy city! A++!"
– Joey, Ohio
"I went out with Captain Rob on a beautiful fall day. I have not sailed much and it was a lovely experience - the city is transformed from the water! The water was calm and I got to try a little sailing myself, which was neat to learn. I can't wait to go out again!"
– Meave, New York
"Loved this experience. It was a perfect relaxing evening on the water. The conversation was easy going and interesting. Nice to get away from the city and glide along the water. In regards to logistics, the meeting up was easy."
– T, Hawaii
"This was an amazing experience. My mother especially loved getting to learn how to sail and was even able to steer the boat. We will definitely visit again thanks to Rob. He was professional, friendly, and a great host."
– Katelyn, Pennsylvania
"Rob was up front about any potential disruptions due to weather. Luckily, the weather cooperated and it was a nice leisurely sail. Great conversation, a couple of nice brews, wind, water, and sun. What more could you want?!"
– Mikquel, Missouri
"Wonderful experience! We did the sunset sail. It was intimate and beautiful! I highly recommend!"
– Sheree, Maryland