Jess

5.0/5 stars 14 reviews
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About Jess

“I have been sailing the Chesapeake Bay and the High Seas for 25+ years.”


Aboard since 2018

From Kensington, MD

Reviews of Jess (14)


  • Jess was an AMAZING host. Great boat, great charter, great service. We enjoyed the bareboat charter ! Thank you.


  • Captain Jess was awesome! The boat was spacious and clean. We enjoyed a perfect day on the water. Would highly recommend and we plan on renting Lagoon 410 in the future!


  • The pontoon boat is a great excursion and Captain Jess is the absolute best! We have booked with him before, and the second time was just as amazing as the first time. We will be back!


  • Amazing experience and an amazing captain! I rented this boat for my birthday last year and it was an absolutely great experience. Everyone had a great time and we are definitely doing this again!


  • Jess was an amazing captain! Super laid back and friendly! We felt extremely safe on the boat and we felt like we were in good hands! Highly recommend him and his super fabulous boat!


  • Amazing day. Jess was fantastic. Would hire him & his incredible boat again in a heartbeat.


  • We had a great time on Imagine! Jess was an excellent captain and sailor, had good recommendations, and made our experience enjoyable and fun.


  • Jess was very welcoming and accommodated everything we asked for to help make my daughter’s 19th Birthday memorable. We will definitely use him for our next boating excursion and highly recommend his services.


  • Highly recommend! This boat is absolutely beautiful. The captain Jess was very professional and also a great time. Would love to book a second trip in the future.


  • Jess was very friendly. The cruise was a great sunset cruise. Everything went well, communication was great.


  • Jess was awesome. His boat was perfect. We had 9 peoplel - 4 adults, 5 kids. Great sailing, touring the rivers and we anchored and swam for a while. The boat was perfect and made for a great day on the water.


  • The boat was GORGEOUS in real life! Everything about the trip was smooth! I enjoyed and will be booking again :)


  • I cannot recommend Jess enough for a sailing charter! I was looking to charter a boat from Kent Island for my sister's bachelorette party, and Jess was far and above the most responsive and courteous person I reached out to. Jess and his wife were incredibly hospitable, constantly making sure if we were comfortable and enjoying ourselves. The boat was very spacious, and more than enough room for our group of 9. We cruised around for several hours, lounging around and enjoying the drinks and snacks we had brought on board. We stopped for a long swim, and Jess provided us with a bunch of floats, tubes, and noodles.

    We had the most amazing day sailing around the bay, and was it was definitely the highlight of our weekend.

    Jess, thank you for making my sister's bachelorette so special!!


  • The Imagine was clean and well-stocked with supplies. It accommodated all 12 of us and four furry friends comfortably!

    Jess is responsive, communicative, straight-forward, and more than accommodating! Despite us arriving way earlier than our scheduled appointment, he allowed us to load up as he prepped the ship and then proceeded to wait about 45mins after our scheduled departure time because our group couldn't get its act together!

    Throughout the process, he handled it all with a great attitude!