Great sailboat rentals near Essex, Maryland.

Sailing Reviews in Essex

1. DZ

   Dunja

   38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

   Captain Shane and Captain Andy were extremely communicative and helpful throughout the entire process from booking all the way through the excursion. The catamaran was clean, beautiful, and the entire charter was a great experience! I would strongly recommend S&S and if I ever host another boating event, I know who to go to!

2. NW

   Nicole

   38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

   I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!

3. 

   Elisabeth

   Welcome Aboard Optimystic! Create a beautiful memory on the water.

   Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

4. 

   Cindy

   Welcome Aboard Optimystic! Create a beautiful memory on the water.

   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!

5. TA

   Tanya

   38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

   This was an amazing experience. We had a great Captain and the whole operation is very well run. Thank you for making this an amazing 70th birthday.

6. TF

   Thomas

   38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

   Trip was very nice and we had a great time. The captain was very professional and the first mate helpful.