Incredible sailboat rentals in Chesapeake Bay, United States.

Sailing Reviews in Chesapeake Bay

1. 

   Dennese

   Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

   Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

2. BF

   Bruce

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

3. 

   George

   Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

   HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

4. KM

   Kelley

   Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

   If you’re looking for a unique and fun way to celebrate a special occasion, or just want to take advantage of the beautiful weather and get out on the water, this is it! I booked a Sunday afternoon trip with friends to celebrate my 36th birthday and it absolutely exceeded my expectations. Captain James was communicative and professional leading up to the trip; he’s a skilled captain and a joy to be around. His catamaran is clean and safe, and equipped with everything you could need, including a sound system and bumpin’ playlist! I will absolutely be booking with him again.

5. CC

   Catie

   Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

   Our experience with James was nothing short of incredible! We booked a short rental for our engagement pictures session, and James’ boat was beautiful, immaculate, and incredibly picturesque. James was quick and incredibly safe as well as a very skilled captain who accommodated multiple pick ups/drop offs for our shoot and did everything in his power to get the pictures we wanted. We would recommend him for photography or a nice sailing day - we will definitely be back!

6. SP

   Sydney

   Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

   We truly could not have asked for a more perfect sailing experience with Captain James!! Our time on the water was so fun thanks to his warmth, hospitality, knowledge, and love for sailing. Our group (including a toddler) loved experiencing the DC area all the way to Mount Vernon. We surprised our friend for her birthday and it was the most fun. I highly recommend this for any and every group looking for a different experience around DC!