It's hot! Cool off on a sailboat!

Book a sail
Daytime Harbor Sail
Leave behind the city’s bustle and set sail on the Chesapeake to experience urban life from the water.
$75 / person
Book now
Sunset Cruise With Local Craft Beer
Sailing is a wonderful respite from the city’s noise and busyness. At nighttime, it’s sublime.
$95 / person includes drinks & snacks
Book now

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
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